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Chicago's entertainment varies from loud and loose to sophisticated and sedate. You'll find classic Chicago corner bars in most neighborhoods, along with trendier alternatives like wine bars and lounges. The strains of blues and jazz provide much of the backbeat to the city's groove, and an alternative country scene is flourishing. As far as dancing is concerned, take your pick from cavernous clubs to smaller spots with DJs spinning dance tunes; there's everything from hip-hop to swing. Wicker Park/Bucktown and River North have the hottest nightlife, but prime spots are spread throughout the city.
Shows usually begin at 9 pm; cover charges generally range from $3 to $20, depending on the day of the week (Friday and Saturday nights are the most expensive). The list of blues and jazz clubs includes several South Side locations: be cautious about transportation here late at night, because some of these neighborhoods can be unsafe. Drive your own car or ask the bartender to call you a cab.
This is home base for Annoyance Productions, an irreverent group best known for hits like Skinprov and Hitch*Cocktails. Two theaters host multiple shows seven days a week, and drinks and snacks are available for enjoyment during the performances. The Annoyance is mostly focused on improv and sketch comedy, but there are also burlesque performances, open-mic nights, and more.
The epicenter of comedy since 1959, The Second City has launched the careers of countless comedy legends, including Bill Murray, Catherine O’Hara, Stephen Colbert, Tina Fey, and Keegan-Michael Key. The revues on the company's historic Mainstage and more intimate e.t.c. space are fully realized sketch comedy shows, but the prescripted material is developed through improvisation in front of audiences. There’s always plenty of time in each show devoted to demonstrating the comedy chops of the quick-witted performers. Most nights, a free improv set after the late show features cast members and invited guests (sometimes famous, sometimes not). UP Comedy Club presents award-winning touring shows, comedy festivals, and special guest performances. In Donny's Skybox upstairs, you're likely to see one of Chicago's many fledgling improv comedy troupes debuting fresh material.
Formerly called ImprovOlympic, I.O. is the city's home for long-form improvisation. The signature piece is "The Harold," in which a team of improvisers explores a single audience suggestion throughout a series of stories and characters until they all eventually weave back together to fit with the original audience idea. There's no drink or age minimum. Seating is first-come, first-served, so be sure to arrive early, especially for weekend shows.
This outpost of the Laugh Factory is part of the chain of comedy clubs that has locations in Hollywood and Las Vegas, among others. Shows like Chicago's Best Standup, The Nasty Show, and Latin XL take place throughout the week while national headliners also appear regularly.
This comedy showcase started in the back room of a Lincoln Square diner, where for years young comics like Hannibal Buress, Cameron Esposito, and Kumail Nanjiani honed their stand-up. The Lodge now has its own venue in Bucktown, where you can find the next generation of comedians working the room most nights of the week.
Devoted to the Chicago-bred tradition of improv comedy, the Revival features top local talents. The theater relocated from Hyde Park to the South Loop in 2024.
Zanies books outstanding national talent and is Chicago's best stand-up comedy spot. Dave Chappelle, Ali Wong, and Jeff Garlin have all performed at this intimate venue.
The springtime Chicago Improv Festival, the nation's largest festival for improvisers, has stages devoted to group, pair, and single improv; sketch comedy; and more.
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