Chicago's culture runs deeper than its skyline. This route pairs the Art Institute's Modern Wing with Hyde Park's Rothko-quiet Smart Museum, Second City's improv stage with Bronzeville's jazz corridor, and the Loop's free public-art trail.
Post-1945 art in a Josef Paul Kleihues building off Michigan Avenue. Strong holdings in Surrealism, Minimalism and Chicago Imagists like Christina Ramberg. Open Tue 10:00–21:00, Wed–Sun 10:00–17:00, closed Mondays. Illinois residents enter free.
The 1897 former central library holds the world's largest Tiffany stained-glass dome, 38 feet across and made of some 30,000 pieces of glass. Free rotating exhibitions fill three floors. Open daily 10:00–17:00 on Randolph Street.
Frank Lloyd Wright's 1910 Prairie School landmark on the University of Chicago campus, with 174 art-glass windows and cantilevered roofs that redefined domestic architecture. Guided interior tours run Thursday–Monday; book ahead as slots sell out.
The University of Chicago's free art museum: Chinese scrolls, German Expressionist prints, Bauhaus furniture from the Bruce Goff collection and contemporary commissions. Roughly 15,000 works in a compact, unhurried building beside a Japanese-inspired courtyard.
The restored 1883 Samuel Nickerson mansion, once called Chicago's 'marble palace', now shows Gilded Age interiors plus Tiffany glass and decorative arts. Open Wed–Sun 10:30–17:00 at 40 East Erie Street, a block off Michigan Avenue.
Founded in a Highland Park church basement in 1974 by Gary Sinise, Terry Kinney and Jeff Perry, Steppenwolf built American ensemble acting and now runs three stages including the in-the-round Ensemble Theater on Halsted Street.
West Town museum devoted to self-taught artists, with a full reconstruction of Henry Darger's one-room apartment and his 15,000-page illustrated epic. Open Tue–Sat 11:00–18:00 on North Milwaukee Avenue in the Noble Square district.
The improv theatre that launched John Belushi, Gilda Radner, Bill Murray, Tina Fey and Stephen Colbert since 1959. Mainstage revues run most nights on North Wells Street, with a free improv set after the last show.
Founded in 1961 in Margaret Burroughs' living room, the oldest independent Black history museum in the United States holds 15,000 works covering the Great Migration, Harold Washington's mayoralty and the Chicago Black Renaissance.
The largest Latino art institution in the country, free since opening in 1987, with 10,000 objects spanning ancient Mexico to Chicano printmaking. Its Día de Muertos exhibition each autumn is the biggest outside Mexico. Closed Mondays.
Two miles of murals along the 16th Street rail embankment plus the tiled facades of 18th Street, where Mexican-American muralists have painted since the 1970s. Chicago Arts District galleries on Halsted open late on second Fridays.
Open since 1907 and once Al Capone's local, the Green Mill still has the booth he favoured and the trapdoor to the tunnels below. Live jazz seven nights, and the Uptown Poetry Slam every Sunday since 1986.