Uptown has a glamorous past as the stomping grounds of Charlie Chaplin, Gloria Swanson and Al Capone. Today it shines as a place to call home for Chicagoans seeking incredible access to the lakefront, public transportation and a vibrant entertainment scene.
Uptown’s early glamour is still reflected in its historic buildings. The neighborhood’s commercial and cultural center is Broadway, with historic Uptown Square at its center.
The area experienced a housing construction boom following the World’s Columbian Exposition. Several of the neighborhood’s luxurious entertainment venues were built in the 1920s reflecting the ornate artistry of the Exposition pavilions.
Uptown continues to be one of the city’s most popular destinations for music lovers, with rock concerts at Aragon Ballroom and Riviera Theatre and jazz at the legendary Green Mill. The jazz venue was a favorite of notorious gangster Capone, who used its underground tunnels to bootleg whiskey and make a hasty retreat from police.
In addition to entertainment, the neighborhood has a number of independent bookstores, art galleries, cafes, and restaurants. The community works to balance new development with a commitment to preserve its past.
Homebuyers have their choice of many housing styles, from lakefront high-rises and vintage walk-ups to new-construction condos and townhomes. A number of beautiful old mansions also line several streets just west of Margate Park.
Uptown is one of the city's most popular destinations for music lovers. For rock and hip hop shows, there's the famous Aragon Ballroom and Riviera Theatre. For jazz, it's the legendary Green Mill, an old Capone haunt that Chicago's most notorious gangster tunneled under so he could bring in bootleg whiskey or beat a hasty retreat from the cops. The tunnels still exist. The neighborhood also has a number of independent book stores, art galleries, cafes and restaurants. Uptown has a very active resident population that seeks to balance new development with the preservation of the neighborhood's past and diversity.
Blue line at Belmont
Brown line at Montrose
Purple line at Belmont
Red line at Wilson
Yellow line at Howard
Milwaukee District North line at Grayland Metra
Union Pacific North line at Ravenswood Metra
Union Pacific Northwest line at Clybourn
Average Sale Price
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Data represents the community area's
average over the past 12 months. All
information deemed reliable, but not
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