Portrait of Chicago: Uptown

Monstrose Harbor looking south, 2018. | Frank Kryzak

Uptown is a quintessential Chicago neighborhood that has its own unique identity but is also a microcosm of 20th and 21st century urbanism in the United States. It’s a common misnomer to say that Chicago has 77 neighborhoods. In fact there are over 200 neighborhoods in the city within 77 official “community areas.”  Uptown is a perfect example of this: Uptown, the community area, encapsulates many different neighborhoods. This article is meant to be a snapshot of various neighborhoods within the larger Uptown community area, and how their histories have shaped what Uptown is today.

History of the Uptown Community Area:

When first founded Uptown was part of Lake View Township, which was north of Chicago’s city limits. Lake View was incorporated in 1857 and covered a massive area: from Fullerton Avenue to Devon Avenue and from Lake Michigan to Western Avenue. The name of the township was taken from one of the area’s first commercial establishments, the Lake View House, which was a hotel located at Sheridan and Grace that opened on July 4, 1854. It was a popular summer retreat for wealthy Chicagoans and local politicians due to its proximity to Lake Michigan. Despite the popularity of the hotel, the area around it remained a remote outpost of scattered farms, summer houses, and saloons for quite a long time. Then in 1872 the Chicago, Milwaukee, and St. Paul (CMSP) Railroad was established as a commuter rail line between downtown Chicago and Evanston, and areas along the rail line, such as Lake View, began to develop. By the mid 1880s, there were three train stations within current day Uptown: Argyle Park, Graceland-Buena Park, and Sheridan Park (Wilson). After that, streetcar lines were built along Lawrence and Broadway (originally Evanston Avenue). In 1889 Lake View Township was annexed to Chicago.

Roughly a decade after Lake View was annexed to Chicago, the Northwestern Elevated Railroad built a partially-elevated line, roughly parallel to the CMSP tracks (which makes up much of the tracks the CTA runs on to this day). At that time the Northwestern rail terminated at Wilson Avenue, but by 1908 the line was extended to Evanston. The Wilson station of the Northwestern had a tremendous impact on the development of Uptown. Uptown’s population exploded and grew rapidly over the next few decades; the area that had remained relatively rural was transformed into a dense urban enclave. By the 1920s, Uptown was one of the most popular and glitzy places in Chicago, with grandiose movie palaces, banks, department stores, smaller specialty shops, dance halls, a beach, jazz clubs, and restaurants contributing to a bustling neighborhood buzzing with nightlife. To this day a decent amount of Uptown’s built environment has retained the early 20th century character of this glamorous entertainment district.

But around the Great Depression, things started to change in Uptown. The extension of Lake Shore Drive to Foster Avenue in 1933 effectively cut the neighborhood off from the lake. Then, during World War II’s housing crisis, former large luxury apartments and hotels were converted into smaller, cheaper units. Though, commercial and residential real estate remained highly valuable in the 1940s.

The 1950s saw changing demographics in Uptown, as the area became accessible to recent migrants and low-income residents due to factors such as neglectful landlords and a plethora of buildings falling into disrepair. During this time, urban renewal policies caused displacement in areas such as Lincoln Park, resulting in thousands of low-income residents in need of affordable housing. The 1950s also saw an influx of Japanese Americans, low-income white people from Appalachia and the South, and mental health patients at the direction of the State of Illinois. At the same time, hundreds of Native Americans began to cluster in Uptown because of federal incentives and opportunity for work. These changes dramatically altered the cultural makeup of Uptown. Incidentally, the high rates of transient residents, available affordable housing, and the aging building stock made Uptown an attractive place for developers. These were the seeds for what would ultimately become a decades-long clash between gentrification forces and longtime Uptown residents.

Developers weren’t the only people becoming interested in the neighborhood. According to the Encyclopedia of Chicago:

“The changes in Uptown’s economy, population, and housing stock drew the attention of residents, business owners, community organizers, and public officials. Longtime residents and people working for commercial institutions created the Uptown Chicago Commission (UCC), which successfully sought designation as a conservation area (1966). The federal government made Uptown a Model Cities Area. New residents joined community organizations, including Jobs or Income Now, sponsored by Students for a Democratic Society; Slim Coleman’s Heart of Uptown Coalition; and the Uptown Hull House’s Organization of the Northeast. Wary of the land clearance that had accompanied urban renewal in Hyde Park and Lincoln Park, they wanted to improve local conditions while keeping Uptown within the means of lower income residents. They protested the building of Truman College (1976), which displaced several hundred residents.”

As that quotes shows, a wide array of social service organizations and institutions opened in the neighborhood to serve the needs of its diverse groups of residents. Uptown’s changing demographics have continued into the 21st century. The neighborhood has attracted people from Central America, Asia, Africa, and the Middle East. Today, Uptown is a fascinating community area full of diversity, rich history, and an array of interesting and unique neighborhoods that tell the complicated story of urbanism in the United States. 

Breaking Down Uptown’s Neighborhoods:

Uptown is quite large and can be generally broken up into eight neighborhoods. The boundaries of these neighborhoods are not marked in any official capacity, however, the map below (put together by Uptown United) provides a useful visualization.

Source: Uptown United



New identifier on Argyle and Broadway, marking the east entry point for the Argyle shared street. | Frank Kryzak

The West Argyle Street Historic District (also known as New Chinatown, Little Saigon, or Little Vietnam at various points) is a historic district in Uptown. It was listed on the National Register of Historic Places on June 3, 2010. Its boundaries are Broadway on the west, Winona on the north, Sheridan on the east, and Ainslie on the south.

The development of the West Argyle Street Historic District from a rural suburb to a dense urban neighborhood is a microcosm for the development of Uptown as a whole. In the early 20th century, residential and commercial development in Uptown concentrated around commuter rail stations (which is now referred to as transit oriented development). Although the land between Lawrence, Foster, Sheridan, and Broadway was first subdivided by John Fussy and Richard Finnemore in 1859, it was William C. Goudy who first brought suburban settlement to the area. Goudy, a prominent Chicago lawyer and state senator, purchased a large tract of land north of the city in 1872, just a year after the Great Chicago Fire. When he purchased it, the land was a wooded and sandy shore that was generally used for hunting. The suburb that then arose in the area became known as Argyle Park to honor Goudy’s mother’s Scottish birthplace.

Development was centered around the Argyle Park train station. 10 years after Goudy purchased the land, he secured the construction of the Evanston and Lake Superior railroad, which began service in 1884 and connected Argyle Park to Chicago with a station on Argyle Street, west of Sheridan. The Evanston & Lake Superior railroad soon after became the new Chicago & Evanston line of the Chicago, Milwaukee, and St. Paul Railway (CMSP), which opened in 1885. By 1908 the Northwestern Elevated Railroad was extended north from its northern terminus at Wilson Avenue, using the tracks of the CMSP. The railroad tracks were later elevated onto an embankment, which the Red and Purple lines run on to this day, between 1914 and 1922.

The extension of the elevated railway and the railroad’s connection to downtown encouraged new residents to move to Argyle Park and nearby communities. The area especially saw an influx of new residents who desired to live near Lake Michigan. By 1908, a number of two- and three-story flat buildings had been constructed within the district, particularly along Winthrop Avenue between Ainslie Street and Winona Avenue. After the new Argyle station was built, the area immediately surrounding the street saw residential development that was increasingly concentrated into larger and more efficient flat buildings and residential hotels.

Argyle Park station, 1908. Source: Uptown History

Vestiges of early commercial development remain along the 1100 block of Argyle Street, on both sides of the elevated tracks. The area around the station was less glamorous and glitzy than other areas of Uptown, like the Uptown Square entertainment district. As opposed to the fancy high-rise apartment buildings east of Sheridan, the people who lived near the Argyle Park station were more middle class, but could still afford to live near the lakefront. Argyle Street was a mixed-use corridor that primarily served the needs of the residents that lived nearby. Many remaining commercial and commercial/residential buildings along the 1100 and 1200 blocks of Argyle were built between 1908 and 1930. Multi-unit residential buildings and residential hotels, which served middle class residents in the 1910s and 1920s, were built on the blocks surrounding the station, including Winthrop, Kenmore, and Sheridan. 

Charles Stanley Building, built in 1918. | Frank Kryzak

The Cascades Dance Hall and Butterfly Cafe at 4936-4940 North Sheridan Road, constructed in 1920 by owner and architect Percy T. Johnstone, provided entertainment options for residences in the immediate vicinity of Argyle Street. Although some residents tried to stop construction on the project, claiming that Sheridan Road was a residential street not suitable for a dance hall, the building was completed in 1921 and pre-dated the larger and more opulent venues in the Uptown Square area such as the Aragon Ballroom, which was completed in 1925. 

5034 N. Sheridan. | Frank Kryzak

There is an interesting religious complex still standing on a largely residential street in the area called the Agudas Achim North Shore Congregation Synagogue (completed in 1925) and Hebrew School (completed in 1949). The synagogue, a Romanesque – revival style building consisting of gray brick and limestone with Baroque and Gothic detailing, had a sanctuary that could hold 1,200 people. The building eventually fell on hard times but then was purchased by FLATS and recently restored and turned into apartments. 

The Agudas Achim North Shore Synagogue located at 5029 was built in 1922 and recently redeveloped into 40-unit apartment by FLATS, a Cedar Street Company specializing in adaptive re-use. | Frank Kryzak

A nondescript building on Argyle in a mostly residential area west of Broadway from the early 20th century holds an incredible amount of significance. This building, located at 1325 W. Argyle, was once Essanay Studios, a movie studio built in 1909. Essanay was founded in 1907 by George Spoor and Gilbert Anderson, and was one of the earliest and largest movie companies in the country. The movie studio was only in operation for about eight years, but many famous early screen actors made movies there, including: Charlie Chaplin, Gloria Swanson, Wallace Beery, Ben Turpin, and Francis X. Bushman.

The former Essanay Studios building is now part of St. Augustine College. | Frank Kryzak

Just north of Argyle, the Bachman house (located at 1244 W. Carmen) was designated a Chicago Landmark in 1992. Architect Bruce Goff created this peculiar home in 1948, when he remodeled a wood house built in 1889 into the home and studio for recording engineer Myron Bachman. The window openings were changed and an exterior cladding of brick and corrugated aluminum was added. 

The Bachman House located at 1244 W. Carmen Avenue. | Frank Kryzak

As Uptown became a popular destination in the 1920s, a large number of residential hotels, which combined smaller and less expensive living spaces with hotel amenities, were built within the Winthrop-Kenmore corridor near the Argyle station. Residential hotels, with and without commercial space on the first floor, can be found on every block in the Argyle Street Historic District. The largest concentration is on the 5000 block of Winthrop, where five residential hotels were built between 1923 and 1926, and are a visible reminder of the rapid urbanization of the area during the 1920s.

A former residential hotel located on Winthrop, just north of Argyle. | Frank Kryzak

The Somerset Hotel at 5009 North Sheridan Road was another landmark hotel built in the neighborhood during this time. The building was built in 1919 and opened for guests by 1920.  It was designed by owner and renowned architect Samuel N. Crowen and contained a total of 441 fully-furnished rooms arranged in 205 suites of one to four rooms each. The building was converted to apartments and is now called The Somerset Place Apartments.

The Somerset Hotel building, pictured here 100 years after it was built in 1919. | Frank Kryzak

The development of residential hotels near Argyle culminated in 1929 with the completion of the 5050 North Sheridan Road building. It replaced an existing three-story, twenty-four-flat apartment building with a 12 story residential hotel. It was considered the first “luxury” residential hotel in the district. The building, designed by the architecture firm of Levy & Klein, contains a Gothic Revival style facade. 

5050 N. Sheridan in 2019. | Frank Kryzak

As the 5050 N. Sheridan residential hotel was being completed in the fall of 1929, the building boom that had transformed Uptown as a whole, from a sleepy suburban settlement to dense neighborhood, was about to end. The Great Depression effectively halted speculative building throughout Chicago (and the country for that matter) through most of the 1930s. Additionally, the extension of North Lake Shore Drive to Foster Avenue in 1933 diverted some traffic away from Uptown’s commercial corridors and cut off the neighborhood’s direct access to Lake Michigan. 

North Lake Shore Drive ended at Foster Avenue with the Edgewater Beach Hotel in the distance in 1938 source: Chicago History Museum

Overcrowding in neighborhoods like Uptown became a significant issue during the housing shortage after World War II when many of the units in the dense residential hotels and apartment buildings were divided into even smaller, one and two room units with cheap rents. The previous residents of the area left and low-income, transient residents moved into the neighborhood. These new residents included displaced coal miners from Appalachia in the 1950s, Native Americans in the 1960s, and patients with mental-illnesses in the 1970s. Southeast Asians also arrived in large numbers during the 1970s and 1980s, many of which settled along Winthrop and Kenmore corridor and opened businesses along Argyle Street. Today, the area is popularly known as Little Vietnam, and remains a vibrant commercial area with a wide array of international businesses and diverse clientele. 

Nha Hang, an excellent Vietnamese restaurant on Argyle. | Frank Kryzak

Indeed, today Little Vietnam is what the Argyle neighborhood is best known as. Beginning in 1975, resettlement agencies in Chicago began placing Vietnamese refugees in the neighborhood. They felt that setting up recent arrivals from Southeast Asia in cheaper housing in and around Uptown made sense, especially since a direct connection to the existing Chinatown was available via the CTA Red Line (The Chinatown stop is located at Cermak Road in the Armour Square community area located south of downtown). These same agencies also resettled former re-education camp detainees and other Asian Americans in and near Uptown in the late 1980s and early 1990s. To this day Vietnamese and people of Vietnamese-decent have remained clustered in Uptown, Rogers Park, and Albany Park, or have moved out into the north and northwest suburbs.

A grocery store along Argyle. | Frank Kryzak

The concentration, not only of Vietnamese, but also of Laotian, Cambodian, and Chinese residents in Uptown spurred a significant amount of Vietnamese and Southeast Asian commercial businesses in the neighborhood.  Since the late 1970s, Southeast and East Asian residents have opened a plethora of restaurants, grocery stores, gift shops, hair salons, video shops, and other businesses targeted to Southeast and East Asian clientele in and around Argyle and Broadway. This concentration of businesses is significant, as it has helped revitalize the retail corridor along Argyle; as the New York Times put it in 1986, “revitalizing a Chicago slum”.

Mural on Argyle. | Frank Kryzak

Vietnamese and Vietnamese -Americans have established a variety of ethnic institutions in Chicagoland for social support and preserving their cultural heritage, and a large concentration of these institutions are located in and near Uptown. The Vietnamese Association of Illinois’ main office on Broadway (there is a satellite office in DuPage) has provided advocacy and social services since it was founded in 1976. 

Mural in an alley adjacent to Argyle. | Frank Kryzak
Argyle Street, 2018. | Frank Kryzak

Interestingly, anyone who has ever taken the train to or from the Argyle Red Line stop might notice a Chinese-style pagoda above the platform. This may seem peculiar, considering Argyle is an area now known as a place representing Chicago’s Vietnamese population, as stated earlier. 

The pagoda above the Argyle Red Line station seen in the background. | Frank Kryzak

According to architectural historian, Erica Allen-Kim, the Chinese-style pagoda at Argyle reflects the fact that many Asian immigrants and refugees in and around Argyle are actually ethnic Chinese. The idea for the pagoda stretches back to the 1960s when Chinese-American businessman and restauranteur Jimmy Wong proposed the creation of a satellite Chinatown on Argyle with a pedestrian mall, pagoda, and reflecting pool. This never materialized but in 1979 Charlie Soo, another Chinese-American businessman, helped create the Asian-American Small Business Association. And then in 1986 he helped partner with the CTA to renovate and paint the Argyle station (at the time in pretty rough shape) in a traditional red-and-green color scheme symbolizing good luck and prosperity. According to a Tribune article, the ticket booth was remade to look like a tea house. In 1991, Soo persuaded the Aon Corporation, which had an office nearby, to fund the pagoda roof design as part of the CTA’s Adopt-A-Station program to help brand the area and spur more economic development.

The Argyle Station has since been renovated, and in 2012 was re-painted, including a mural called “Cornucopia” by Lynn Basa, and a red-and-green “Asia on Argyle” sign installed. The refurbished pagoda roof “functions as an architectural and spatial landmark, serving more as billboard and signifier of ethnicity,” according to Kim. Now Argyle, from Broadway to Sheridan, is Chicago’s first “shared street”. Completed in 2015, the street is now a space where pedestrians, bicyclists, and people driving cars share the street. There are permeable pavers, infiltration planters, bollards, the street was raised, and all curbs were eliminated to create a plaza like feel. This type of street is popular in places like Europe, and is often referred to as a Woonerf. The street has become a place for community events, and now hosts the Argyle Night Market every summer. The activation of the main commercial corridor in the neighborhood signifies a bright future for the area, while honoring its past and the diverse groups of people who still make Argyle Street their home.

Argyle Street in Uptown is Chicago’s first “shared street”. | Frank Kryzak


800 Hutchinson in Buena Park, built in 1908. | Frank Kryzak

In 1887 James B. Waller, a resident of the Lake View township sold 35 acres of land that he owned to real estate speculators and developers. Waller’s original house is now the site of St. Mary of the Lake church, which was built and dedicated in 1917. This land, including the Waller home, is located in what is now called Buena Park.

Sheridan Road and Buena Avenue, exterior view of the Waller residence.
The original Waller home. Source: Chicago Public Library

Buena Park makes up the southeast corner of Uptown and abuts the lakefront. It became known as one of the wealthiest areas of Uptown almost immediately after it was developed. When people think of Uptown, it’s unlikely that Buena Park is the image that their mind conjures. In Buena Park you will find unique and pastoral streets that are described as “terraces,” which include large, ornate single family houses on relatively large and manicured lots. Renowned architects such as George Maher, Louis Sullivan, and a young Frank Lloyd Wright designed an array of Prairie, Arts and Crafts, and Beaux Arts style houses in the neighborhood. Unlike other parts of Uptown, apartment buildings historically were harder to come by in Buena Park, as the character of its built environment largely resembled a wealthy suburb as opposed to a dense urban neighborhood.

Montrose Avenue looking south on Broadway and Sheridan Road into Buena Park, 1891. Source: Chicago Public Library

Perhaps the most famous and intriguing section of Buena Park is the Hutchinson Street Historic District, which includes its namesake street. In the late 19th century, Charles Scales bought a parcel of land that includes present-day Hutchinson Street. This tract of land was located between Fremont (now Hazel) Street and Halsted Street (now Clarendon Avenue), just north of Buena Avenue. To encourage development for this newly acquired land, a street named Kenesaw Terrace, was built through the middle of it.  Scales hired Chicago architect George Washington Maher to design his family house and it was completed in 1894. The beautiful Queen Anne style house stands to this day at 840 W. Hutchinson.

The Scales House, located at 840 W. Hutchinson, built in 1894. | Frank Kryzak

There are other houses that are still in existence on the original parcel of land designed by G. W. Maher. These include the Mosser house at 750 W. Hutchinson, built in 1902; the Lake House at 832 W. Hutchinson, built in 1904; the house at 839 W. Hutchinson, built in 1909; and the Seymour house at 817 W. Hutchinson, built in 1913.

Claude Seymour House, built in 1913, located at 817 W. Hutchinson. | Frank Kryzak

In October 1936, Kenesaw Terrace was renamed to honor a prominent Chicago businessman and civic leader, Charles L. Hutchinson. He was the president of the Corn Exchange National Bank (which his father founded) and also served as a director of the Northern Trust Company, the Chicago Packing and Provision Company, and the Chicago Street Railway Company.

734 Hutchinson, built in 1913. An example of the Mission style of architecture, the two-story stucco residence was designed by T.S. Urbain. | Frank Kryzak
4250 N. Marine Drive (view of the Hutchinson Street side of the house). | Frank Kryzak
This classical revival style home at 716 Hutchinson was built in 1901. | Frank Kryzak
707 Hutchinson is dwarfed by a high rise in the background. | Frank Kryzak
A one and a half story house made of grey stucco at 715 Hutchinson. | Frank Kryzak
747 Hutchinson, built in 1909. | Frank Kryzak

As a whole, Buena Park developed along the same trajectory and timeline as other neighborhoods within Uptown. In the late 19th century a train station was established at what is now Buena and Kenmore. In 1885, the Chicago, Milwaukee & St. Paul (CMSP) Railway opened a steam rail line connecting the suburbs of Lake View township and Evanston to Chicago, running between Calvary Cemetery and Union Station. By mid-1889, trains ran as far north as Maple Avenue in suburban Llewellyn Park (which is now present-day Wilmette).

Construction of L tracks at Sheridan Road
Construction of the Elevated tracks at Sheridan Road and Irving Park Road looking northwest toward Buena Park, 1901. Source: Chicago Public Library

Then, around 1900, the Northwestern elevated and the CMSP began negotiations to extend the elevated company’s trains north to the city limits and on to Evanston over the steam railway’s tracks. At that time, the Northwestern elevated ended at Wilson and Broadway, adjacent to the CMSP Sheridan Park station. An agreement between the two was reached in 1904, but finalization of the terms was delayed until 1907. “L” service was extended north of Wilson to Central in Evanston in 1908 over the now-electrified CMSP tracks. CMSP stopped their steam commuter operations from Wilmette to the Sheridan Park station at the same time as L service was extended over CMSP’s tracks. The CMSP line continued running two trains a day between Union Station and Sheridan Park from June 1908 until 1917, when the limited service was ended and the tracks were only used to haul freight. 

The Northwestern L and CMSP railway Buena station, source Chicago-L.org
Post card of Buena Park, view from Buena Station, N.W. Elevated R.R. looking East
View from the Buena elevated station in 1920. Source: Chicago Public Library
View from near where the Buena station once stood, 2018. | Frank Kryzak

In the 1910s, the Northwestern began elevating the ground-level tracks between Howard Street and Leland Avenue (one block south of Lawrence and north of Wilson). By early 1922, the new elevated, four-track main line between Lawrence and Howard was completed. At this point, the CMSP continued its freight operations north to where the L began operating on the CMSP’s former right-of-way, so an interchange yard was needed where the freight railroad could exchange cars with the L and vice versa. The site selected was a narrow strip of land along the CMSP’s old main line between Graceland Cemetery and the elevated structure between Montrose and Irving Park, called the Buena Yard. 

The CMSP’s Graceland station was at the center of the yard, even though it had ceased to function as a passenger station five years earlier in 1917. Initially, there were two CMSP Graceland station houses, one on the east side of the tracks and another on the west side, partially on cemetery land. The L structure that now exists was actually built over the east station house and the Buena station platform was built above it. Part of the old CMSP station was used for the L station, while the rest of it was used as a freight office. By 1924, the west station house was being used as an office by the Graceland Cemetery Association; and eventually was demolished in the 1960s. Also, in the early 1960s, the east building (which had been sitting vacant since the Buena L station closed in 1949—just two years after the CTA took over operations for elevated rapid transit in Chicago) was partially demolished.  The remaining half was likely used for storage after that, and at some point the entire station was removed. Today, there is hardly a trace that either the west or east station houses ever existed.

Like much of Uptown as a whole, the area of Buena Park surrounding the Buena Yard was considered rough in the later days of freight service. According to Chicago-L.org, there were many nights when switchmen didn’t want to get off the freight locomotives alone, and vandalism became an increasingly costly issue. Due to escalating costs, lack of customers, and safety concerns, CTA’s freight service came to an end in the 1970s. This meant that the last freight cars returned to Buena Yard, spelling the end of the yard itself, and subsequently the strip of land was abandoned for many years.

Burned out apartments at 4136 N. Broadway in Buena Park near Buena Yard, 1975. Arson and deteriorated buildings were commonplace in Uptown in the 1970s. Source: Uptown: Portrait of a Chicago Neighborhood in the Mid-1970s by Robert Rehak

But then, in the early 1990s during Mayor Richard M. Daley’s administration, the City entered into a public-private partnership to create a park on the abandoned land. The park transformed the former Buena Yard with native trees, grasses, wildflowers, jogging and walking paths, new sewers, lighting, and a new alley running underneath the elevated track structure. The Chicago Park District named the site Challenger Park in memory of the 1986 Challenger Space Shuttle disaster.

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Challenger Park, 2018. The imprints of train tracks are still visible. | Frank Kryzak
Buena Yards and the former St. Paul Graceland station, source: Chicago-L.org

As mentioned earlier,  many perceived the area around Buena Yard, along with most of Buena Park, as a rough neighborhood. An interesting article from the New York Times covers gentrification in Buena Park in the late 1980s. By that time, Buena Park was largely considered “blighted” and then a developer purchased buildings and vacant land mostly in the 4200 and 4300 blocks of North Kenmore, and began redeveloping the Buena Park Historic District. The developer’s goal was to “bring new life to the last blighted pocket in the changing neighborhood.” Buena Park was listed on the National Register of Historic Places in 1984.

St. Mary of the Lake Church, established in 1917 at 4200 N. Sheridan. | Frank Kryzak
Uptown on New Year's Day, image 63
Buena Park on New Year’s Day, source: UIC
High rises of Buena Park in 2019, with the Immaculata High School and Convent in the foreground. The Immaculata campus is listed on the National Register for Historic Places and is a Chicago Landmark. | Frank Kryzak

In the mid 1980s, the Chicago Park District worked with Greenpeace Great Lakes and Uptown community leaders to renovate a historic rock garden in Lincoln Park (the park itself, not the community area) and rename it the Peace Garden. Improvements included replanting perennials in the garden’s multitiered beds, replacing missing stones, repairing the original water cascade that trickles down to a lower basin, painting a mural in the adjacent underpass, and creating a narrow arched mosaic above the east entrance to the underpass. Mayor Harold Washington dedicated the Peace Garden in May 1986.

Peace garden along the lakefront in Buena Park. | Frank Kryzak

Just to the west, a prominent building once located in Buena Park, the Sheridan Theater, was located at 4036 N. Sheridan and opened in 1927. It was a treasured cinema in the neighborhood, but fell on hard times by the 1990s and was eventually demolished and replaced by a mid-rise residential building.

Sheridan Theatre in 1928. Source: Cinema Treasures
A drug store which is now the site of the present day Holiday Club, with the Sheridan Theatre in the background. Source: Uptown Chicago History
1947–Sheridan Road and Irving Park Road, looking north. Source: Chicago History Today


Montrose Harbor looking south, January 2017. | Frank Kryzak

What distinguishes Clarendon Park and Margate Park from other parts of Uptown is the presence of park space, beaches, and Lake Michigan. It is an area of high rises, dense courtyard buildings, and natural beauty. The focal point of this area of Uptown is Montrose Beach and Montrose Harbor. A unique aspect of the beach is, not a dog-park, but a dog-beach at its north end. 

The Clarendon Park field house, which is located between Montrose and Wilson, is home to the Garfield-Clarendon Model Railroad Club and to Kuumba Lynx, a 20-year-old art youth development organization that “presents, preserves, and promotes hip hop as a tool to reimagine and demonstrate a more just world.” Kuumba Lynx is an important community anchor and has even been featured on the Netflix show “Rhythm and Flow”. And surrounding the field house is Clarendon Park, which is rich with recreational amenities; it has a variety of fields for soccer and softball, as well as basketball courts.

Lake Michigan from near Montrose Harbor, January 2017. | Frank Kryzak
Amazing tinted aerial of Uptown, 1928, Chicago. Click to enlarge. Looking north from Irving Park (then called Graceland), you can see the Marine Hospital, which took up quite a bit of land. The Disney Magnet School is there now. Notice that Lake...
Tinted aerial of Uptown, 1928. Looking north from Irving Park (then called Graceland). At the time Lake Shore Drive terminated at Clarendon Beach. This gives a really good perspective on how much landfill was used to create the parks and beaches east of Lake Shore Drive in the 1930s. Source: Calumet 412

A gem along the lakefront near Montrose Harbor is the Montrose Point Bird Sanctuary, which is a stretch of shrubs, trees, and a meadow (and is colloquially known as the Magic Hedge). An important rest stop for migratory birds, every spring and autumn thousands of birds from over 300 different species pass through or nest within the sanctuary. The following video was taken in early spring, the sounds of birds can be heard along with a visible cardinal chirping.

Montrose Beach, May 2018 |Frank Kryzak
People flying kites in early spring on Cricket Hill, near Montrose Harbor, May 2018. |Frank Kryzak
Wilson Avenue Beach in 1919, long before outer Lake Shore Drive cut off Clarendon Park from the lake, The Clarendon Park field house can be seen in the background.
811 apts uptown
Clarendon Park with the recently completed Eight Eleven apartments in the background, summer 2019. |Frank Kryzak
Clarendon Park field house 1916. Notice it was directly beachside on the lakefront. This area is now recreational fields, and the lakefront is now significantly further east. Source: Chicago Public Library
Montrose Avenue beach
Montrose beach, 1887. Source: Chicago Public Library

Just a few blocks south of the Clarendon Park field house sits Joseph Brennemann Elementary School (at 4251 N. Clarendon). The school was built in 1963 by famous architect Bertrand Goldberg (who designed the iconic Marina City towers which famously grace the cover of Wilco’s album Yankee Hotel Foxtrot). The building now looks relatively unremarkable, but underneath the existing roof lies curved concrete structures that were part of Goldberg’s original design.

Front of Brennemann School, from Clarendon Ave. the corrugated metal rising from the roof now covers all of the original classroom caves. (Jason Marck/WBEZ)
Brennemann School, source: WBEZ
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Goldberg’s original design for Brennemann, source: bertrandgoldberg.org
The lakefront, north of Montrose beach looking north toward the northern boundary of Uptown at Foster, and Edgewater beyond that, January 2017 |Frank Kryzak
Lawrence Avenue beach
Lawrence Avenue beach, 1910. Source: Chicago Public Library

The Clarendon Park & Margate Park area of Uptown isn’t all beaches, water, and parks though. The built environment east of Sheridan Road is a fascinating amalgam of vernacular architecture and history.

Wilson Avenue east of Sheridan has a mixture of buildings from the early 1900s next to buildings from this decade, as shown in this photo. The new building on the right is a transit oriented development (TOD) completed in 2019. |Frank Kryzak

Nearby, the Wilson Abbey building- which now houses a small theater, a coffee shop, meeting rooms, and office spaces for rent- was built in 1917 and designed by brothers Cornelius W. Rapp and George Leslie Rapp, who also designed the Riviera Theatre and Uptown Theatre. It was originally built as a car dealership, operated for a while as a tavern for bootlegging, and then as a strip club called the Backstage Lounge.

931-939 W. Wilson, now known as Wilson Abbey. |Frank Kryzak

The Uptown Theatre wasn’t the only large movie house in Uptown. Before that, there was the Pantheon, located just north of Wilson on Sheridan. Designed by Walter Ahlschlager for the Lubliner and Trinz  movie theatre chain, it opened in 1918.

Pantheon Theater, 4642 N. Sheridan. Source: Uptown History

The Margate Park area, which is just north of Clarendon Park is made up of historic mansions, mid-rises, and terra cotta hotels that reflect the area’s development in the bustle of the early 1900s, much like the rest of Uptown. A standout business in the area is Big Chicks, which is an iconic LGBTQ bar founded in 1986 by Michelle Fire. She also owns the burnch restaurant Tweet, located right next door.

Big Chicks and Tweet, spring 2018. |Frank Kryzak


Sheridan Park, 2018. |Frank Kryzak

Sheridan Park is generally bounded by Clark on the west, Montrose on the south, Racine on the east, and Lawrence on the north. Within the neighborhood, there is the Sheridan Park Historic District—a residential area composed primarily of single-family homes, smaller apartment buildings, and larger apartment hotels that date back from the 1890s to the 1920s. Before the neighborhood urbanized, it was an area frequented by Native Americans. A path called the Green Bay Trail, which ran from Fort Dearborn all the way to Green Bay, was regularly traversed by Native Americans (present-day Clark Street follows the path). But by the mid-1800s, the neighborhood would become inextricably linked with Graceland Cemetery. 

Traveling east or west through the neighborhood, between Montrose and Lawrence, you can notice a relatively steep incline (by Chicago standards). This “hill” is called the Graceland Spit, which is a ridge rising about 20 feet above the flat plain of geological Lake Chicago. Graceland Cemetery and St. Boniface Cemetery were both initially built on this ridge because of its well-drained, sandy soil. 

In April 1861, the Graceland Cemetery Corporation was formed to subdivide and market a portion of its land north of Montrose, the area currently occupied by the The Dover Street Landmark District, which runs through the neighborhood along Dover Street and partially along Beacon Street. The boundaries of the subdivision were St. Boniface Cemetery on the north, Racine on the east, Sunnyside on the south, and Clark on the west. This speculative real estate development was named the Sheridan Drive Subdivision due to its proximity to Sheridan Road along the lakefront, which had been recently built. 

Sunnyside Avenue
Sunnyside Avenue looking west, 1891. Source: Chicago Public Library

The subdivision attracted Chicago businessman Bryan Lathrop, the nephew of Graceland Cemetery founder Thomas P. Bryan, and the president of the cemetery. Bryan Lathrop was interested in real estate and personally financed lot sales in the subdivision by offering buyers trust deeds (i.e. mortgages). Aside from his real-estate career, Lathrop was also a key figure in the establishment of several Chicago cultural institutions, including the Newberry Library, the Art Institute of Chicago, and the Chicago Symphony Orchestra.

Row houses in the Dover Street Landmark District. |Frank Kryzak

In 1891, Ossian Simonds, notable for his work in Graceland Cemetery, was commissioned to design the layout and landscape for the new subdivision. His design featured angled streets and large building lots, with terraced front lawns and plenty of large trees. These streets break from the traditional Chicago street grid, and the lots are larger than the typical Chicago lot size. The slight diagonal direction of the streets follows the natural elevated ridge in the land and Clark Street.

Leland Avenue & Magnolia Street
Magnolia and Leland, 1891. Source: Chicago Public Library

In 1891, the same year the Sheridan Drive Subdivision was created, the Sheridan Park train station (long ago demolished) was built at Wilson and Broadway on the Chicago, Milwaukee & St. Paul (CMSP) railway. This establishment of public transportation nearby helped usher in development and an influx of people into Sheridan Park. The Romanesque-style train station was similar to other stations from the same period that still can be found in Chicago’s North Shore suburbs. 

Sheridan Park train station at Wilson and Broadway, source: Uptown Chicago History

The large lots and lush lawns in Sheridan Park give the neighborhood a relatively spacious character. Its oldest buildings are large single family homes that were built between 1891 and 1920. The smaller apartment buildings date from between 1897 and 1927, and the residential hotels were built generally in the 1910s and 20s. The dominant building type in the neighborhood is the six-flat, but with a significant amount of single-family homes and two-flats as well. The setbacks on Dover and Beacon were maintained throughout the area’s later development, so that even the larger apartment buildings from the 1920s have yards. 

Mann’s Million Dollar Rainbo Gardens, once located at Clark and Lawrence. It was an entertainment destination during the Jazz Age and eventually became an ice skating rink, a roller rink, and a music venue.  Larry Fine, who was invited to join the Three Stooges, worked here.

By 1950 Sheridan Park was one of the densest neighborhoods in Chicago, with over 12,000 residents. In the 1940s landlords began converting many large six-flat apartments into single room apartments – sometimes up to 30 of them in a given building, due to a housing shortage. Uptown’s density of small, short-term rental apartments attracted white southerners and folks from Appalachia who were searching for work, and by the 1950s thousands of them migrated to Sheridan Park.

Carols 1
Carol’s Pub, a honky tonk bar opened in 1972 and recently re-opened, 2019. |Frank Kryzak

As this low-income transient population began growing in the neighborhood they were generally seen as a source of blight by established wealthier residents. These “blighted” buildings were largely single room occupancy (SRO), residential hotel, and dense apartment buildings generally located along Lawrence and Wilson. One of the most notorious low income housing buildings was the Wilson Men’s Club Hotel, a vacant department store at Wilson and Racine converted into a cubicle residency in 1929, which now in 2020 is being redeveloped as micro-apartments. The housing stock, due to overcrowding, high tenant turnover, and neglectful building owners, began to decline in the 1960s. By 1960 dilapidated residential hotels with rooms lacking bathrooms, were increasing throughout Central Uptown. More than 1,800 dilapidated residential hotel rooms were located in Sheridan Park.

In 1955, wealthy citizens of Uptown formed the Uptown Chicago Commission (UCC) to try and combat these changes in the neighborhood. Sheridan Park’s western boundary, Clark Street, consisted of another auxiliary commercial strip. The street had a distinct Swedish character and a well-organized business organization, the North Clark Businessman’s Association. Uptown at this time was still largely defined by its commercial establishments such as restaurants, taverns, lounges, concert halls, and theaters. These places increasingly served the neighborhood’s low income population.

In 1969 a Federal urban renewal plan for Uptown, which was pushed for by the UCC, was approved along with other neighborhoods in Chicago such as Woodlawn, Hyde Park, and Lincoln Park. Before the plan was approved, many neighborhood groups came together to form the Uptown Area People’s Planning Coalition (PPC) in order to influence the urban renewal plan. Their goals included not displacing residents, keeping tear-downs at a minimum, and instituting cooperative and non-profit ownership structures to keep rents affordable; the UCC resented the PPC. During this time the New Left also started to organize Latinxs, African Americans, Native Americans, and other multiracial groups in the neighborhood. These New Left community organizations started to challenge the UCC and their vision for the neighborhood (to resist these new social and class changes), and community tensions continued to rise. Also at this time, a myriad of social services were brought to Uptown due to the neighborhood’s designation by the City of Chicago as a Model Cities program recipient. 

Eventually the neighborhood fight over the site for Truman Community College in the 1970s exemplified the ongoing battle in Uptown over community development, urban planning, policy, displacement, gentrification, and equity. Wealthier residents, including the UCC, favored the demolition of rundown buildings (“slum clearance”) and replacing them with anchor institutions such as community colleges to fix the neighborhood’s “problems”. Organizations such as the PPC, however, pushed back on this, arguing that Truman Community College would only hurt the neighborhood by displacing thousands of residents. The PPC sought to keep and help the neighborhood’s low income residents with an affordable housing development on the site called Hank Williams Village that would include welcome centers, health clinics, and nursing homes. However, the UCC effectively wanted to push these residents out and attract new middle- and upper-class residents.

Unsurprisingly, Uptown’s wealthier residents and the UCC won, and in 1976 Truman College opened at Wilson and Racine, displacing between 1,800 and 4,000 residents—many of whom were low-income.

The south west corner of Wilson and Racine, 1955. This site would later be occupied by Truman Community College, source: Uptown History

In the 1970s and 80s, the spiritual successor of the New Left called the “Coleman-Shiller movement” took hold in the neighborhood. The movement was named after Walter Coleman, a community activist with experience in the Student Nonviolent Coordinating Committee and the Black Panther Party, and Helen Shiller, a left-wing activist who was the Alderman of the 46th Ward from 1987 to 2011. They led the Heart of Uptown Coalition, which was formed in 1972, and then worked  for Harold Washington’s campaign for Mayor in 1983. In the 70s and 80s they led the expansion of social services in Uptown, forming the Uptown People’s Health Clinic, the Uptown People’s Law Center, and the Uptown People’s Community Center. And they continued to lead the charge in advocating for more affordable housing in the neighborhood and retaining its existing low income residents. Affordable housing added to the neighborhood mostly took the form of large, privately-owned, publicly-subsidized affordable housing buildings. They were primarily funded by HUD  grants and allowed a large number of low-income residents to stay in the neighborhood. Uptown as a whole, but also notably Sheridan Park, throughout the 60s, 70s, and into the 1980s was largely seen as notoriously rough. Many residents were without jobs, a large number of buildings had deteriorated or were burned down, and gang activity and crime were rampant.

South west corner of Wilson and Magnolia, 1976. This building was destroyed by fire (likely arson), and this was a relatively common sight in the neighborhood in the 70s. Source: Uptown: Portrait of a Chicago Neighborhood in the Mid-1970s by Robert Rehak

But by 1985, in some aspects, the neighborhood was on the verge of gentrification, and subsequently the Sheridan Park Historic District was created. At the time, a new demographic was starting to reside in Uptown because of its vintage housing stock and proximity to Lake Michigan. And the way these new residents would “reinvent” the neighborhood involved historic preservation legislation. One of these residents, Daniel Bluestone, successfully led a campaign to have Buena Park listed on the National Register in 1984. This was a pivotal moment because there was now a blueprint for other developers to carve out areas in Uptown (and other communities) that would be deemed “historic” and effectively usher in gentrification within those districts.

When the Sheridan Park Historic District was created, most residents of Sheridan Park or Buena Park at that time had never heard of these names before, they simply called where they lived Uptown, or in Sheridan Park’s case, The Heart of Uptown. These “new” names for historic districts were critical in the perception of “reinvention” of these places. To most middle and upper class people in the Chicago area, the name Uptown had quite the negative connotation, so these name changes were crucial for real estate brokers, developers, and investors. Renaming sections of the neighborhood was a way to eschew the social, economic, and racial diversity of Uptown for an idealized and presumably whitewashed version of what the neighborhood could be. Immediately following the historic district designation, the name Sheridan Park could been seen advertising many of the newly renovated apartment buildings. While the historic designation for Sheridan Park, and subsequently many other areas around the city as well, was ultimately a good tool for preserving the character and history of the built environment and ushering in investment to fix many formerly dilapidated buildings, the question persists—who actually benefited from this? 

By the 1980s and 1990s many affordable housing building owners began to consider opting out of the federal programs, which would displace most residents. Allies of the Coleman-Shiller movement organized a task force which helped rally residents to put pressure on HUD to “preserve” the buildings by giving additional incentives to owners either to remain in affordable housing programs or to sell to non-profit corporations. 

Sheridan Park in many ways has been a perfect microcosm of the fight between affordability and social justice, on one side, and with development and gentrification pressures on the other. This struggle continued in Uptown as a whole throughout the 20th century and still to this day. Perhaps D. Bradford Hunt and Jon B. DeVries in Planning Chicago put it best when they describe the socioeconomic uniqueness of the neighborhood:

Decades of conflict have produced a stalemate and perhaps an equilibrium. Gentrification has not overwhelmed the poor, nor have significant concentrations of poverty, affordable housing, and social service agencies led the community to a “tipping point”. Uptown’s trajectory does not fit with traditional patterns of urban change. Perhaps ironically, a high degree of conflict over planning has produced Chicago’s most diverse community, with extraordinary ranges of ethnicity, race, and income.”

Apartment buildings in Sheridan Park, 2018. | Frank Kryzak
Sheridan Park, 2018. |Frank Kryzak
issel 2
The historic terra cotta-faced Issel Building at Clark and Wilson in Sheridan Park, built in the  1920s |Frank Kryzak

One example of the neighborhood’s diversity is the Black Ensemble Theater, which was founded in 1976 by Jackie Taylor, an actor, playwright, and producer. It began as a small community arts organization and has grown to be a vibrant nationally and internationally renowned arts institution. The Black Ensemble Theater is recognized as one of the most diverse theaters in the country, and as a leader in the African American and mainstream arts communities.  In 2011, the Black Ensemble Theater Cultural Center opened at 4450 N. Clark Street in Sheridan Park, as the theater’s first permanent home.

The Black Ensemble Theater Cultural Center, 2018. |Frank Kryzak

As Megan E. Heim Laframbois notes in her book “Reframing the Reclaiming of Urban Space: A Feminist Exploration into Do-It-Yourself Urbanism in Chicago“, the dichotomy between people of varying socioeconomic standing has manifested itself in Uptown’s public spaces. The Sunnyside Mall was built in 1975 as a landscaped and tree lined car free plaza that stretches for two blocks between Magnolia and Beacon. 

The Sunnyside Pedestrian Mall, created in 1975. |Frank Kryzak

The space has been activated the past few years with events such as community movie nights and Halloween festivals by community organizations, but the space has also been described as a place for drugs, violence, and gang activity. The tensions that exists in regards to who uses the space and what they use it for is representative of the constant push-pull of such a diverse neighborhood.


Uptown Square in the 1930s, with the Sheridan Trust and Savings Bank/ Uptown National Trust building in the middle of the frame dominating the Uptown skyline. Source: Uptown Update

The Uptown Square Historic District, radiating from the intersection of Lawrence and Broadway, is what most people likely consider the beating heart of Uptown, with its grand theaters and entertainment venues.

According to the Uptown Square National Register report:

“The district’s collection of 52 buildings and one structure includes a range of significant architecture reflecting the period of significance from 1900 to 1950, including turn-of-the-century storefronts with apartments, grand Spanish Baroque and Moorish entertainment facilities, Classical Revival terra cotta-clad office buildings, an Art Deco post office, and Art Deco and Venetian Gothic apartment hotels. The district is distinguished from its surroundings by its architecture, its scale, and its organization as a cohesive commercial and entertainment district.”

It may be difficult to imagine it now, but Uptown Square was once a grassy and sandy stretch of land, up until the mid-1800s. 

Train tracks at Wilson Avenue and Broadway, looking north
Train tracks at Wilson Avenue and Broadway, looking north, 1897, source: Chicago Public Library

In 1891 the Sheridan Park rail station on the Chicago, Milwaukee, & St. Paul (CMSP) line was built close to where the present-day Wilson Red Line station exists. This commuter rail station was incredibly important for the residential and commercial development of the area. 

The Sheridan Park station, built in 1891 near present-day Wilson and Broadway. Source: Chicago Rails
Train tracks at Wilson Avenue and Broadway, looking north
Montrose and Broadway looking north, 1897. The Sheridan Park train station at Wilson and Broadway can be seen in the background. Source: Chicago Public Library

The beginning of the Northwestern Elevated Railroad’s operation in 1900 only further accelerated development in Uptown. Between 1900 and 1910, the neighborhood’s population grew by 60%. This growth rapidly changed the area’s character, which had previously been mostly scattered single-family residences with a few small two and three-flats, and the occasional retail store on the ground floor. At this point, larger multi-story apartment buildings began to replace single family homes and two-flats. The oldest remaining buildings in the Uptown Square district are three apartment buildings constructed on the north side of Lawrence between Winthrop and Kenmore: the Middlekauf Apartments (built in 1901 and located at 1042-48 W. Lawrence), the Lawrence Apartments (built in 1902 and located at 1058 W. Lawrence), and the Fleur-de-lis Apartments (built in 1905, and located at 1064 W. Lawrence). The first permanent elevated station at Wilson, designed by William Gibb in 1900, was a one-story building on the elevated tracks and was the northern terminal for the line. This station was serviceable for the first couple of years it existed, however the increased ridership and frequency of trains became a problem and in 1907 the Lower Wilson station opened to support the at-grade repair yard and shops at the terminal station (Wilson Yard and Shops) and to handle some rush-hour and express trains. The Wilson Yard and Shops was Northwestern Elevated’s chief maintenance facility and storage yard. To maximize storage capacity on what was a relatively small space, they built a large two-story complex between Montrose and Wilson which opened in 1901. 

A year after the lower station was built, in 1908, the Wilson station was converted from a terminal to a through station when the Northwestern Elevated opened its extension to Evanston over the electrified ground-level tracks of the CMSP.  This was made possible by a short extension of the elevated structure across Broadway, then down a two-track ramp to the CMSP tracks.  Not long after the extension was created, Uptown was booming with development, and the triangular property on the north side of Wilson, between the elevated tracks and Broadway, was developed as a commercial property.

The property was leased by Peter C. Stohr, the assistant to the traffic director of the Union Pacific Railroad in Chicago at the time. He commissioned Frank Lloyd Wright to design an office and retail building adjacent to the Wilson station. Wright designed the building with a one story portion tucked under the elevated tracks and a prominent three-story elevation along Broadway. The building was one of the biggest commercial buildings in Uptown when it was completed, but it wasn’t around for long.  In 1922 it was demolished to make way for the CTA Wilson L (Gerber station house) building designed by Arthur U. Gerber, which opened in 1923. Recently, the Gerber building has been partially restored as part of the Red and Purple Line Modernization program and will be home to the Chicago Market food co-op, likely to open in 2020.

Gerber Building, 2019. |Frank Kryzak
The Peter C. Stohr Arcade Building, which housed a variety of businesses including a grocery, photography studio, and real estate office was built in 1909 and was designed by Frank Lloyd Wright. The building anchored the Wilson station for just over a decade until the Gerber building was erected in its place and has stood ever since. Source: Chicago-L.org
The original track-level Gibb- designed station house. Source: Chicago-L.org
Lower Wilson Station before the elevated
The lower Wilson Avenue station. This was once the terminal before the “L” was extended north. This station opened on March 5, 1907. The intent was to alleviate crowding at the upper Wilson station, already in use. Lower Wilson closed on August 1, 1949, early in the CTA era. Source: The Trolley Dodger

The Wilson Shop building continued to be used in some capacity for over 90 years. In 1949 the Lower Wilson station ceased to be used for revenue operations, but the lower yard remained in use, even though all trains now ran to Howard. But, by the 1970s the lower yard had been demolished.

By the 1990s, the Wilson shop had become outdated and no longer had the capacity for maintenance on newer CTA train cars. As part of the impending through-routing of Howard service with the Dan Ryan (it has previously been run south to Englewood-Jackson Park), a plan was formulated to expand and modernize the Howard Yard and build a new Howard Shop. The new Howard facility opened in 1993 and the main maintenance and storage functions were moved from Wilson to Howard. The Wilson Shop continued to be used for auxiliary purposes but unfortunately burned down in 1996.

Wilson Yard & Shops, looking north in 1964. Source: Chicago-L.org

A few years after the fire, 46th Ward alderman Helen Shiller began getting local residents and business owners together to come up with a development plan for the Wilson Yard and Shop site, and in 2001 the city created the Wilson Yard TIF to facilitate its development. The project was mired in years of controversy and became representative of the ongoing fight regarding development and displacement in the neighborhood.

After almost three years of meetings, Shiller settled on a plan that called for a movie theater, a Target, reconstruction of an existing Aldi, smaller retail spaces, and a mix of affordable and market-rate housing. But the plan kept evolving and the theater was never built. The residential portion of the project ended up consisting of two ten-story buildings of affordable housing: one with 84 units for individuals and families and the other with 99 units for seniors.

The Wilson Yard development, source: Radiant Manufacturing

Back in the early 1920s though, residential and commercial development continued at a rapid pace and Uptown was a nightlife destination with a rich tapestry of restaurants, theaters, cafes, dance halls, and shopping. Uptown Square became a shopping alternative to Chicago’s downtown and by the mid-1920s became one of the most important commercial centers outside of downtown (namely the Loop). 

One of the tentpole businesses in the neighborhood was the Green Mill Gardens, which was a popular haunt for actors from Essanay Studios nearby. It originally opened in 1907 as Pop Morse’s Roadhouse, a bar that garnered much of its business from people visiting nearby Graceland and Saint Boniface cemeteries. After Charles E. (Pop) Morse died in 1908, the building was purchased by Charles Hoffman, and in 1909 he built a frame pavilion on the site and opened a small beer garden. Then in 1911 the site was purchased by restaurateurs Tom and George Chamales, and renamed it the Green Mill. Although the origins of the name are unclear, it is largely believed that the new name referenced Paris’s Moulin Rouge (Red Mill), but with a different color to avoid association with the nearby red-light district.  In 1914 the Green Mill was renovated and the Green Mill sunken gardens were added. The sunken gardens had a central open courtyard with a stage for entertainment which were separated from the street by arcaded walkways and the enclosed restaurant building. The sunken gardens weren’t the only addition to the Green Mill; the improvements also included a two-story, u-shaped commercial building with offices, a restaurant, indoor ballroom, and a “Della Robbia Room,” which was described as “the rare conception of the famous artist, outfitted in the costliest, though modest style, in rich marble and tile.”  Interestingly, a large portion of the gardens and the commercial building were located on what is now the site of the Uptown Theatre. A massive green windmill that faced the corner of Lawrence and Broadway was installed on the top of the commercial building, beckoning visitors to see famous singers and musicians play the stage. 

Newspaper from 1914 announcing the opening of the Green Mill Sunken Gardens. Source: My Al Capone Museum

In 1921 Tom Chamales decided to add a modern, more permanent building that would be viable throughout the entire year. When completed, the new two-story brick building featured an enlarged cabaret room on the second floor. A new main entrance served as an entry point for both the upstairs cabaret and the outdoor gardens behind the building. In the 1920s, during prohibition, the Green Mill became a notorious spot in Chicago’s gangster history. It is said that Jack “Machine Gun” McGurn, an associate of Al Capone, owned a portion of the club during this time. Tunnels under the bar, which were originally built to transport coal, were likely used by Capone’s associates to smuggle in alcohol or to escape raids; there are tunnels that still exist under the entire building and across the street. Legend has it that there was a table reserved for Capone himself. If you go in the Green Mill today, it’s the first table past the booths on the north wall where you can see both entrances. However, this is debatable as the Green Mill Cabaret during prohibition was located on the second floor of the building and the entrance was a couple of storefronts north where Fiesta Mexica currently is located. For a period of time it wasn’t even called the Green Mill, in the mid 1920s it was named the Montmartre Cafe and the space where the Green Mill is currently located was a jeweler. It can still be inferred that the tunnel located underneath the bar in the present-day Green Mill was used for smuggling in alcohol or escaping raids, even if that space wasn’t yet a cocktail lounge. It also may very well have been a speakeasy, but it’s unlikely there was a booth for Capone…if anything, there may have been a booth for him where Fiesta Mexicana currently is, but most likely it would have been upstairs in the actual cabaret.

The corner of Lawrence and Broadway in 1925 or 1926 shortly after the Uptown Theatre was opened. As you can see in the photo, at this time the Green Mill was renamed to the Montmartre Cafe and the space where the current Green Mill exists was a jeweler. Source: Uptown Update

In the 20s and 30s the Green Mill (or Montmartre Cafe depending on the time) was incredibly prestigious, as star entertainers of the era routinely performed on its stage, including Billie Holiday and Al Jolson, along with cabaret icons like Texas Guinan. Professional offices occupied a portion of the second floor and retail merchants rented the storefronts on the first floor. For years a Walgreen’s Drug Store occupied the corner retail space (which today is occupied by the Broadway Grill). A grand showroom opened on the second floor, and it featured cabaret shows and dancing.  In 1923 Chamales sold the garden property behind the building to the Balaban and Katz organization, who would go on to build the Uptown Theatre on the site. In 1925 the Green Mill was under new management and the name was changed to the Montmarte Cafe, only to be changed back to the Green Mill later on when Guinan briefly operated it in 1930. According to the Chicago Tribune, the police quickly shut the club down following a shooting involving its manager. The building then was nearly destroyed by a fire in 1933. The upstairs Green Mill cabaret room continued to operate on a sporadic basis through the 1930s and 1940s, at times as a ballroom called the Paradise and later the El Morocco. 

The Green Mill, 1930. Source: My Al Capone Museum

According to Charles A. Sengstock Jr., the current site of the Green Mill jazz club, the second door north of Lawrence, dates back at least to the 1930s.  And, according to the current owner Dave Jemilo, it was a cocktail lounge through the mid 1940s, owned by the Batsis brothers, and was a watering hole for a mostly neighborhood crowd and some after-hours patrons from the nearby Uptown Theater, Riviera Theater, and the Aragon Ballroom. Stanley Schwickler then purchased the lounge in 1952, according to Jemilo. From about 1938 until 1986, Steve Brend was a bartender at the Green Mill and later purchased it from Schwickler (Brend had previously worked for McGurn). He also became the unofficial historian of the club until he sold it to Jemilo in 1986. Based on Jemilo’s previous experience and success with owning jazz clubs, he saw in the Green Mill lounge the ambience he wanted for a full-time jazz venue. After he bought it from Brend, he said, he had to give the club a much-needed face-lift and restored many of its original elements. 

The Green Mill Gardens, source: John Chuckman

Since then, the Green Mill has returned to glory as one of the premier jazz clubs in the world. Additionally, every Saturday since 2012 the Green Mill hosts The Paper Machete, which is a free weekly “live magazine” that features comedic essays and character monologues based on the current headlines, written and performed by artists from the worlds of stand-up, sketch comedy, improv, theater, live lit, and journalism in addition to music and variety acts.

The Green Mill, 2018. |Frank Kryzak

Back in the late 1900s and early 1910s, when the Green Mill was originally expanding, new options for entertainment, lodging, banking, and shopping were opening up along Broadway between Wilson and Lawrence.  The Wilson Avenue Theater (originally the Standard Vaudeville Theater) at 1050 West Wilson, the oldest theater in the Uptown Square District, opened in 1909.

The Wilson Avenue Theater, 2019. | Frank Kryzak

Although the theater was converted to a bank by the 1920s, it had served as the district’s only theater until the Lakeside Theater opened at 4730 North Sheridan Road in 1914. The Wilson Avenue Theater will soon be home to the Double Door music venue. The Lakeside, a two-story Classical Revival building designed by Chicago architect Ralph C. Harris, was the first movie theater to open in Uptown. The theater was part of a group of venues operated by the Ascher Brothers, who were significant movie theater operators in Chicago during the 1910s and 1920s.  The building now houses Alternatives, which is a “comprehensive, multi-cultural youth development organization that operates as a support system for more than 3,000 of Chicago’s young people and their families each year”. 

Lakeside Theatre, Chicago, IL
The Lakeside Theater building, which now is the home to Alternatives, source: Cinema Treasures

In 1915, the Sheridan Trust and Savings Bank, which was founded in 1909 at the corner of Wilson and Broadway, also built a new space at 4728 N. Broadway, fronting Lawrence and Broadway. This was part of the development of a triangular shaped site at the intersection of Leland, Broadway, and Racine. The building’s “flatiron” shape was a popular form for office and bank buildings at the time. But, in 1924, the bank would build a larger building across Broadway, and the building at 4728 N. Broadway would be taken over by Loren Miller & Company Department Store. The bank moved to an eight story Classical Revival building on the southeast corner of Broadway and Lawrence. This new and incredibly ornate building even featured a ceiling imported from Italy. Just four years after the building was completed, a four-story addition was built so the bank ended up rising 12 stories above the street. In 1931, the Sheridan Trust & Savings Bank failed, and in 1937 the Uptown National Bank moved in, which remained in the space until 2003. In 2008, the building was designated a Chicago Landmark.

Sheridan Trust and Savings/ Uptown National Bank building, recently purchased by Cedar Street Companies. | Frank Kryzak

The Loren Miller & Co. Department Store, which took over the bank’s original site, started next door at 4720 N. Broadway. It was founded in 1915 by Loren Miller, a former department manager at Marshall Field’s. When Miller opened this massive 5 story department store, he was hoping to establish an economic anchor that would attract other businesses to the area while capitalizing on the popularity of the small stores, hotels, and other businesses that were already present. This proved to be successful, between 1915 and 1926, the area around Broadway between Wilson and Lawrence emerged as one of the most vibrant retail, commercial, and entertainment centers outside of downtown.

Another immense change that altered the character of Uptown during this period was the construction of several grand movie theaters designed by legendary theater architects Cornelius Ward Rapp and George Leslie Rapp. They had designed many of Chicago’s most exquisite movie theaters including the Tivoli Theatre (since demolished), the Chicago Theatre (designated a Chicago Landmark in 1983), the James M. Nederlander Theatre, the (Cadillac) Palace Theatre, and the Uptown Theatre. Rapp & Rapp also built the Riviera Theater, at 4746 N. Racine, in 1917. The Riviera was the second theater opened by Balaban and Katz in Chicago and the second movie theater designed for the company by Rapp & Rapp. It had a 2,500-seat theater as well as offices, retail stores, a billiard hall, and restaurants in an adjacent three-story commercial building. The Riviera has been a concert venue for popular acts since the 1970s. 

The Riviera, which is now a prominent music venue, 2019. | Frank Kryzak

By 1924 there were over 20 movie theaters in and around Uptown. Yet, while Uptown had other movie theaters, the Uptown Theatre (opened in 1925 and designated a Chicago Landmark in 1991) stood out among the rest. The building features Spanish Baroque Revival ornamentation, as well as 4,381 seats, which made it the largest theater in the world at the time of its opening. The opulent theater was nicknamed the “magic city”, and it boasted a vast mezzanine, three lobbies, fountains, paintings, grand staircases, immense chandeliers, and walls covered in rococo ornamentation. It still has the largest seating capacity of any theater in Chicago. The inside of the theater included floating clouds and twinkling ceiling lights; “state of the art” air conditioning; and a perfuming system built under the seats. While watching elaborate stage acts that preceded the movies visitors were treated to music from, at the time, the most expensive Wurlitzer organ ever built, or sometimes a full orchestra. The Uptown ushered in the golden era of the Uptown Square District, and the intersection of Broadway and Lawrence truly became the heart of the neighborhood. 

Remnants of the Green Mill’s outdoor “sunken garden” during construction of the Uptown Theatre. Source: Uptown Update
One of the lobbies of the Uptown Theatre. Source: Chicago Architecture Center

For its first few years in existence, the Uptown Theatre presented silent movies and live vaudeville acts, then musicals and movies with sound in the 1930s. By the 1960s it was losing money so the Wurlitzer organ was sold along with many of the lavish interior paintings and statues. After that, in the 1970s it became a live music venue hosting high profile artists such as Bruce Springsteen and the E Street Band. But sadly in December 1981, it suffered major flood damage when storm drain pipes froze and burst. This marked the end of concerts at the theater and it has sat vacant ever since. However, good news was announced recently, the Uptown Theatre will apparently soon be rehabbed and will hopefully re-open in the early 2020s

During the 1920s, Uptown also featured a large number of dance halls, ranging from small rooms  to more elaborate spaces with elegant interiors and big bands. The most elaborate of these dance halls was the Aragon Ballroom which opened at 1100 W. Lawrence in 1926. This Spanish-Moorish architectural masterpiece was designed by the architecture firm of Huszagh & Hill in collaboration with renowned theater architect John Eberson. The creative theater interior, which features a space that mimics a Spanish courtyard, includes ceilings decorated with twinkling stars and clouds to imitate night skies.

The Aragon Ballroom. | Frank Kryzak

The Aragon was commissioned by Greek immigrants, George and Andrew Karzas, who had started with a restaurant and nickelodeon on the South Side before deciding to capitalize on the popular new trend of movies. They purchased a small string of movie theaters and, in 1921, opened the Woodlawn at 1236 E. 63rd Street (since demolished), one of the city’s first neighborhood movie theaters. After having success in the movie theater industry, the brothers decided to open a dance hall aimed at more upscale clientele. The Trianon, which was located at 62nd and Cottage Grove (since demolished) opened in 1922 and was widely popular. This prompted them to build the Aragon, and it was a sensation just like the Trianon. 

Along with the Aragon, the Wilton Hotel was completed in 1926 just down the street at 1039-53 W. Lawrence. It was built in an elaborate Venetian Gothic Revival style and its eight-story brick-and-terra cotta facade was a wonderful addition to the growing Uptown business district.  The use of these revival architectural styles was not confined to residential hotels, ballrooms, and theaters; it was also used for commercial buildings. The Uptown Broadway building was completed in 1927 at the northeast corner of Broadway and Leland.  In addition to shops and offices, the building once had the largest indoor mini-golf course in Chicago, and features an intricately ornamented, blue, grey, yellow, and cream-colored terra cotta facade. Its Spanish Baroque Revival-style design also pays homage to its neighbors, the Uptown Theatre and Aragon Ballroom.

The Uptown Broadway building, 2018.| Frank Kryzak
The Uptown Broadway building, 2018. | Frank Kryzak

In 1928, the architecture firm of Huszagh & Hill designed the 12-story New Lawrence Hotel, located at 1020 W. Lawrence, not in the revival styles they had used for their work on the Aragon Ballroom and Wilton Hotel but in the Art Deco-style. The New Lawrence was a residential hotel with 500 rooms, a rooftop garden, solarium, “ice cooled water,” a swimming pool, and an indoor putting green lit by skylights. The designs of these buildings on Lawrence, as well as the numerous buildings with elaborate terra cotta facades, helped define the area’s distinct built environment, which is still intact today.

Meanwhile, Loren Miller’s Uptown Department Store was continuing to grow. After expanding the store’s operations into the former Sheridan Trust and Savings Bank the store expanded again three years later. This time to the south when Miller acquired the former Plymouth Hotel building. In 1930 a campaign by Miller to have the area around the intersection of Broadway and Lawrence recognized as “Uptown Square” was finally successful, when the City Council officially designated the district.

Goldblatt's Department Store
Racine and Broadway, 1989. Source: Chicago Public Library

In 1931 Loren Miller sold his store to the Goldblatt Brothers, a Chicago-based discount department store chain.  Goldblatt’s was known for its low prices and its neighborhood-based operations. The company’s original flagship store, at 1613-35 W. Chicago Avenue, built from 1921 to 1928, is a designated Chicago Landmark.


The repeal of prohibition in 1933 brought new changes to the area. New bars were opened and old ones, such as the Green Mill Tavern, officially “re-opened.”  In 1939 a new Post Office was built at 4850 N. Broadway as a project of the Works Progress Administration (WPA). The building’s linear design and minimal ornamentation stood in stark contrast to the ornamental terra cotta buildings that were constructed in the 1910s and 1920s. By the time the United States entered into World War II, Uptown’s nightlife actually experienced a new surge of popularity. Soldiers and sailors stationed at nearby military institutions, including the Great Lakes Naval Training Station and Fort Sheridan, had easy access to the district via public transportation. 

In the years following World War II, the popularity of the district as a commercial and entertainment destination began to wane.  The Aragon Ballroom remained open until March 31, 1958, when a fire and explosion in the restaurant next door caused extensive damage. Following a $250,000 remodeling project, the Aragon reopened, but the already small crowds returned in even smaller numbers and it was sold in 1963. In the following years it was used as a roller rink, a disco, an indoor flea market, a bingo hall, a boxing arena, and, finally, as a venue for live music concerts. Despite the diversity of uses over the years, the building’s beautiful exterior and interior remain largely intact. It is presently a popular music venue. Although the Plymouth Hotel was demolished in 2003, the Uptown Square District has retained the majority of its significant buildings. The New Lawrence Hotel, which was converted to senior housing in the 1980s, is currently being rehabilitated for market rate apartments, and in recent years the Uptown National Bank building and Loren Miller Department Store building have undergone rehabilitations, with the latter now housing First Ascent, a rock climbing gym. The Uptown Square district may not be what it was in its early 20th century heyday, but it is still vibrant and has retained its rich cultural and architectural history. And with transformational projects like the rehab of the Uptown Theatre and the opening of the Double Door, the future for the Uptown Square district is very bright.

Uptown Lounge, 2018. | Frank Kryzak
Broadway just north of Montrose in 1926. You can see the exquisite blue and white terra cotta building, torn down for the Wilson Yards redevelopment, a view of the Arcadia Ballroom with Wilson Yards behind, the McJunkin building, and far off in the distance the rooftop marquee of the recently completed Uptown Theatre. source: Uptown History


In a way, Uptown as a whole (and other nearby neighborhoods) would never have been established were it not for Graceland Cemetery. As the cemetery became a draw for people, eventually the area around it saw a great influx of residents, development, and train stations. The Cedar Lawn (1869), Buena Park (1860), Sheridan Park (1894), and Edgewater (1887) developments in Lake View Township brought middle-income and wealthy residents to the area.

Graceland was established in 1860 by Thomas Bryan, a prominent Chicago lawyer. He initially purchased 80 acres of land to establish the cemetery and in 1861 received a perpetual charter from the State of Illinois. He soon thereafter hired prominent landscape architect H.W.S. Cleveland to design the grounds. At the time of its inception and for a few decades after, Graceland was located north of Chicago’s city limits in the Lake View Township. After some negotiation with the town’s residents, Graceland expanded east and northwest from its original 80 acres to its present-day acreage of 119. In the 1870s the cemetery’s paths and plots were uniformly sodded, and the fenced and curbed plot boundaries were eliminated by Cleveland, with architectural and engineering input by William Le Baron Jenney, a renowned architect at the time. This helped created the Victorian park style atmosphere that was then further enhanced by landscape designer, Ossian Simonds. He favored the use of native plants to create a pastoral landscape for the cemetery, which is one of the reasons the cemetery is, to this day, a significant draw for tourists and local residents alike. Along with its beautiful natural landscapes, visitors to Graceland are treated to a place full of famous historical Chicago figures and architectural majesty. 

Graceland Cemetery, autumn 2017. | Frank Kryzak
Graceland Cemetery, autumn 2017 .| Frank Kryzak

The area hugging the western border of Graceland is commonly referred to as Graceland West (although it has also been referred to as Cemetery West, as it is in the Sundowner song “Cemetery West”). This small residential neighborhood at the southwestern corner of Uptown is bounded by Ashland, Montrose, Irving, and its namesake cemetery (along Clark). It’s a neighborhood replete with large single-family houses, Victorian mansions, and some dense apartment buildings. A notable resident who lived in the neighborhood for over a decade is the actor Joan Cusack. 

The former Joan Cusack residence, 2019. This mansion was likely built in the 1860s for early settler Conrad Sulzer. | Frank Kryzak
A residential block in the Graceland West neighborhood. | Frank Kryzak


The famous Andersonville water tank in the background of residential buildings in Andersonville, 2019. | Frank Kryzak

While the Andersonville neighborhood is generally associated with Edgewater, the southern portion of it is actually located in Uptown. Interestingly, Edgewater wasn’t initially a separate community area from Uptown. It became its own (and the 77th and final in Chicago) community area in 1980. Because Andersonville is not generally considered part of Uptown, I don’t provide any further information here but have included some photos to give a sense of the built environment.

Hopleaf Bar, anchoring the south end of Andersonville (near the northern border of Uptown) since 1992. | Frank Kryzak
Guesthouse Hotel, 2018. | Frank Kryzak
The South East Asia Center, 2018. | Frank Kryzak
The former Schlitz Tied House (now the South East Asia Center) at 5120 N Broadway, at Winona, 1956, Chicago. The historic bar still stands, now the South East Asia Center. Source: Calumet 412