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Windy City Magazine
Discover Chicagoland and the Businesses That Drive It
Downtown Chicago

South Loop

The South Loop starts at Ida B. Wells Drive, the old Congress Parkway, and runs south past Roosevelt Road toward Cermak, between the river and the lake. The neighborhood straddles two community areas, the Loop and the Near South Side, according to WTTW, and belongs to the Downtown Chicago group. Printers Row is the strip between Clark and State from Harrison to Roosevelt, where the old Donnelley and Rand McNally printing buildings became apartments in the 1970s, and the Printers Row Lit Fest takes over Dearborn each September.

East of Michigan Avenue the neighborhood opens into the south end of Grant Park and the Museum Campus, with the Field Museum, Shedd Aquarium and Adler Planetarium on a peninsula next to Soldier Field and Northerly Island. Prairie Avenue was the city’s first mansion district; Glessner House from 1887 still stands, and Marshall Field and George Pullman had houses on the block. Dearborn Park, built on old rail yards in the 1980s, and the towers around Roosevelt and Michigan hold most of the population, which has grown faster than almost anywhere else in the city. The Roosevelt Collection and Motor Row on Michigan south of 14th add shops and music venues.

Housing and prices

Housing is loft conversions in the printing buildings on Dearborn and Plymouth Court, townhouses in Dearborn Park and Central Station, and high-rises along Michigan, Wabash and Indiana from the 2000s building boom. Construction dates run from the 1890s to the present. Condos typically range from about $250,000 for a one-bedroom to $1 million for large lake-view units. These are broad editorial estimates as of September 2026, not appraisals. The South Loop stays cheaper than the Loop or Streeterville for comparable square footage, which is a large part of the appeal.

Getting around

Roosevelt is the main station, where the Red, Green and Orange Lines meet at State and Roosevelt. The Red Line also stops at Harrison, the Blue Line at LaSalle on the north edge, and the Green Line at Cermak-McCormick Place. Metra Electric and South Shore trains stop at Van Buren Street, Museum Campus/11th Street and 18th Street. The 1, 3, 4 and 12 buses cover Michigan, Indiana and Roosevelt, and the 146 runs to the Museum Campus. Lake Shore Drive has ramps at Roosevelt and 18th, and the Dan Ryan and Stevenson start at the neighborhood’s south end. Divvy docks are everywhere near the museums. Street parking is metered on the main streets with residential permit zones in Dearborn Park and on the side streets east of Michigan; Soldier Field game days fill the lots.

Where to eat, drink and shop

Coffee and a Cuban sandwich at https://windycitymagazine.com/business/cafecito/ on Congress is the Columbia College routine. Two diners cover the rest of the day: https://windycitymagazine.com/business/eleven-city-diner/ on Wabash for a corned beef sandwich and https://windycitymagazine.com/business/white-palace-grill/ on Canal, open around the clock. https://windycitymagazine.com/business/flo-and-santos/ on Wabash is a Polish tavern with thin-crust pizza and pierogi, and https://windycitymagazine.com/business/half-sour/ on Clark Street is the neighborhood bar and restaurant near Printers Row. https://windycitymagazine.com/business/kaseys-tavern/ on Dearborn has poured in Printers Row for decades, and https://windycitymagazine.com/business/reggies-chicago/ on State near Cermak is a rock club with a bar and rooftop.

The museums are the reason most visitors come. The https://windycitymagazine.com/business/field-museum/, https://windycitymagazine.com/business/shedd-aquarium/ and https://windycitymagazine.com/business/adler-planetarium/ sit side by side on the Museum Campus, and https://windycitymagazine.com/business/glessner-house/ on Prairie Avenue runs tours of the 1887 Richardson house.

Businesses in South Loop

Directory listings in the South Loop, in alphabetical order.

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