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 map

Open Houses in Uptown

Here are 12 Open Houses out of 177 listings in Uptown

Featured Uptown Listings

Here are 12 out of 177 listings in Uptown


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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Sales Prices VS. List Price
Data represents the community area's average over the past 12 months. All information deemed reliable, but not guaranteed.

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