Chicago knows how to put on a show, with some 200 theaters sprinkled around town. Improv comedy was born here and continues to headline on legendary stages. The drama scene draws equal acclaim, with many productions exporting to Broadway.
Want to find the top performances in town? Read on for our top theater picks in Chicago. A tip to get you started: check Hot Tix, which sells discounted tickets to theaters around the city.
Immerse in the drama at Steppenwolf Theatre
Steppenwolf Theatre is Chicago’s top stage, and mounts provocative plays by its Pulitzer Prize–winning, movie-star-filled ensemble that includes John Malkovich, Tracy Letts, Gary Sinise, and Laurie Metcalf. Performances take place in the main Downstairs Theater, in-the-round Ensemble Theater (where all seats are within 20ft of the stage) and cabaret-style 1700 Theater (which hosts emerging actors and playwrights). Hang out after the show in Steppenwolf’s cozy cafe, and you might end up having a drink next to the performers.
How to score a ticket: It’s best to book tickets for Steppenwolf Theatre a few weeks in advance online. That said, a small number of $20 tickets go on sale for same-day shows; call the box office (312-335-1650) right when it opens at noon and see if you get lucky. Tuesday tickets are pay what you can (available by phone only).
Go big at a Broadway show in the Theater District
Glitzy touring productions set up shop in the Theater District downtown, where several century-old, neon-lit playhouses cluster around State and Randolph Sts. The opulent, seven-story Chicago Theatre is star of the lot. Cadillac Palace Theatre (with an interior based on the Palace of Versailles) and Nederlander Theatre (with stunning East Asian architectural elements) stand out among the others for seeing the likes of Back to the Future: The Musical and Harry Potter and the Cursed Child.
How to score a ticket: Broadway in Chicago handles tickets for all of the theaters except the Chicago Theatre. Buy online, or save around $10 per ticket in handling fees by buying in person at the box office (hours vary for each theater, so check before heading out). Same-day tickets often are available, especially for Tuesday, Wednesday and Thursday shows.
Laugh out loud at Second City
Second City is the comedy venue that put improv on the map and launched many superstars’ careers. Bill Murray, Stephen Colbert, Tina Fey, Steve Carrell and more honed their wit at the nightly shows here. The slick Mainstage, e.t.c. Theater and UP Comedy Club host the most hilarious and polished ensembles riffing on politics and pop culture in ever-changing sketch revues. Several smaller stages put on the up-and-comers.
How to score a ticket: Book tickets on the Second City website. Prime-time weekend shows on the Mainstage often sell out a few weeks in advance. Late-night shows and midweek shows can be booked a few days ahead of time and typically are cheaper.
Watch 30 plays in 60 minutes at the Neo-Futurist Theater
The small Neo-Futurist Theater is known for its funny, irreverent, oddly moving show The Infinite Wrench. Members of the diverse young troupe write and perform their own mini plays, which range from brazen to sad to foulmouthed, funny and/or semi-nude. The clock starts, and the actors race to get through the repertoire, which becomes ever more manic as the deadline approaches.
How to score a ticket: Buy tickets for the Neo-Futurist Theater online a few days in advance. Shows are Friday and Saturday at 10:30pm and Sundays at 7pm. Seating is first-come, first-served, so it’s wise to arrive when the doors open 30 minutes prior to showtime.
Behold mind-blowing tricks at the Chicago Magic Lounge
Find the secret entrance to the Chicago Magic Lounge behind a wall of laundry machines, and you’ll see amazing feats of prestidigitation nightly. For The Signature Show, magicians conjure at your cabaret-style table, followed by an hour-long stage performance where they read minds, levitate and make things disappear.
How to score a ticket: The small room often sells out. Reserve Chicago Magic Lounge tickets online two weeks in advance for prime-time weekend shows, and one week in advance for late-night and midweek shows. If that fails, you can always buy a drink in the 1930s-style bar where a roaming magician is on duty (no ticket required).
Join the carnival at Sideshow Gelato
Fire-eaters, sword-swallowers, magicians and jugglers perform on the stages inside this frozen treat shop. Kids shows take place on Saturday afternoons and involve an illusionist who pounds a nail into his head with a pie plate. Saturday evening cabaret shows add storytelling, dancing and stunts to the mix. Special one-night-only shows bring out acts like the 6ft-tall, man-eating chicken.
How to score a ticket: Check Sideshow Gelato’s website for the performance schedule and reserve tickets a few days in advance. Seating is first-come, first served. Walk-up tickets often are available. All shows are pay-what-you-want.
Be part of the scene iO Theater
iO Theater is one of the hotbeds for improv comedy, where performers create shows on the spot based on suggestions the audience shouts out. See it in action with the Improvised Shakespeare Company, where the troupe ad libs wacky plays in Elizabethan verse, and Improvised Jane Austen, where the players freestyle with Regency-era tropes.
How to score a ticket: Buy tickets from iO’s website a day or two in advance. Compared to Second City, iO has cheaper and easier-to-get seats.
See comedy and fringe shows at the Den Theatre
If Saw: The Musical (a parody of the popular horror film), a queer take on Glengarry Glen Ross or a bawdy storytelling show sound like your kind of entertainment, check out the Den Theatre. The hip space in the heart of Wicker Park also hosts well-known stand-up acts on its main stage. Four smaller stages carry the fringe shows.
How to score a ticket: Buy tickets for the Den Theatre a few days in advance (earlier for big-name comics). Some of the stand-up shows also have a two-drink minimum.
Explore an offbeat show at Chopin Theatre
Chopin Theatre is another great representative of Chicago’s storefront theater scene. Set in a 1918 building full of shabby-chic charm, it features oddball, thought-provoking plays, concerts and literary events. Everything plays here, from puppet festivals and Polish jazz jams to campy original works about Scooby Doo.
How to score a ticket: Buy tickets on the Chopin Theatre website. It depends on the event, but you’ll likely want to buy at least a few days in advance.
Feel the beat at the Harris Theater for Music and Dance
From Indian classical violin shows to hip hop dance acts, there’s always something interesting going on at this underground venue next to Millennium Park. More than 30 cutting-edge performing arts troupes call the Harris Theater home, including the Chicago Opera Theater, Ballet Chicago and Hubbard Street Dance Chicago.
How to score a ticket: Buy tickets via Harris Theater’s website. While some shows sell out months in advance (looking at you, Chicago Philharmonic), others have same-day tickets available.
