At night, Chicago comes alive, showing off its sophisticated and progressive energy. Locals have their favorite stomping grounds, while visitors are often tempted to flit from one spot to the next, eager to check off as many evening activities as possible. Performance art is manna to Midwesterners. Our theaters—Steppenwolf, Lookinglass, Goodman—are breeding grounds for Tony-award winning playwrights and directors. Hubbard Street Dance and Joffrey Ballet are internationally acclaimed. If laughs are what you’re after, comedy clubs like Second City and IO have finessed improvisation into high art. And of course, America’s favorite pastimes are the lifeblood of Chicago’s sports bars and stadiums. The spectacle of an evening Bears, Bulls, Blackhawks, or Cubs game is an event in and of itself. Love music? Venues swell across the city with contemporary jazz songstresses, reverberating rock riffs, and the throbbing bass of indie DJ beats. Trust me, it will be a late night.
Before Tina Fey, Steve Carrell, John Candy, and Mike Myers were household names, they were all getting their start at the comedic incubator, Second City. This brand of witty, mash-up, improvised sketch comedy has been entertaining Chicagoan audiences for 50 years. When you spend an evening at the provenance of television’s funniest talents (Comedy Central; Saturday Night Live) you’re guaranteed to laugh out loud.
If you love thought-provoking, sometimes disturbing drama, book tickets for an evening production at Steppenwolf. With eleven Tony Awards for groundbreaking acts such as August Osage County and The Grapes of Wrath, this is not your average regional playhouse. Steppenwolf is one of America’s finest ensemble theaters—and it is the best spot in the city to see emerging and established give career-defining performances.
Once a down-trodden, Prohibition-era tavern, this Wicker Park enclave has retained its grittiness and emerged as a vibrant nightlife institution. Music aficionados will find an impressive cross-section of local bands and established touring acts. Rumor has it that the Rolling Stones once popped in for an impromptu set. Comedians often frequent this celebrated stage.
Bowling and martinis, anyone? Lucky Strike is a bowling alley that doubles as swank cocktail lounge. The 18 lanes, lacquered and illuminated by hallogen signs, are smartly separated from the restaurant and bar, both serving firmly non-bowling alley fare. Enjoy the ancho chili citrus chicken and coconut shrimp at the plush cocktail bar.
Gene Siskel Center
If you pine to see the highlights of the Cannes Film Festival, or watch obscure, Oscar-nominated shorts, the Siskel Center will be your cinematic Shangri-La. An homage to the late local film critic, Gene Siskel, this theater traffics only arthouse productions, documentaries, cinema classics, and international flicks. Now playing? A revival of rare and beloved Hitchcock films.