Chicago Improv: Where to Catch Comedy Shows in the Windy City

The Chicago improv is scene is legendary. Dozens of famous comedians and comic actors have emerged from Chicago to become stars in movies and on Saturday Night Live, from Bill Murray to Tina Fey to Stephen Colbert.

If you’re visiting Chicago, you may be curious about checking out an improv or sketch comedy show. Fortunately, there are a ton of options!

second city theater - chicago improv

Improv, of course, is the genre of comedy theater in which the jokes and scenes are made up on the spot by the performers, often with the help of audience suggestions.

Second City is the most famous and enduring improv spot in Chicago, but many smaller theaters have daily shows as well.

Here’s a list of the best venues to visit, created based on my own experience living in Chicago for many years and attending a lot of these shows.


Chicago Improv and Sketch Comedy Theaters and Venues

1 Second City

Neighborhood: Old Town
Address: 1616 N Wells Street, Chicago IL
Price range: $30-50
Food and drink: Full kitchen and bar
Popular shows: Oh, the Places You’ll Glow!, Best of the Second City, Improv Brunch
Notable alumni: Stephen Colbert, Tina Fey, Chris Farley, Amy Poehler, Bill Murray, Mike Myers, Steve Carell, Eugene Levy, Joan Rivers

Ask anyone about Chicago improv troupes, and they will most likely mention Second City first. This one has a legendary aura due to the dozens of pop culture icons it has produced.

Second City has produced countless stars of televsion and film for decades now, going all the way back to actors and performers like Alan Alda, Eugene Levy, and Joan Rivers.

Shows currently running at Second City include Clued In, an improvised murder mystery; Baby Wants Candy, an improvised full-band musical; and Shamilton, a Hamilton-like improvised musical based on a random famous person chosen by the crowd.

2 iO! Theater

Neighborhood: Old Town / Lincoln Park
Address: 1501 N Kingsbury, Chicago IL
Price range: $20-35
Food and drink: Full kitchen and bar
Popular shows: Improvised Jane Austen, Harold Night, Improvised Shakespeare, Voila the Improvised Musical
Notable alumni: Cecily Strong, Andy Dick, Seth Meyers, Amy Poehler, Tina Fey, Eric Stonestreet, Vince Vaughn, Bob Odenkirk

IO Theater

The venue known as iO has some of the city’s most popular shows, seven nights a week. iO has a lot of long-form, storytelling improv shows, which are popular with audiences.

That’s where you can find shows like Improvised Shakespeare, which has been running for nearly two decades, creating a brand new Shakespeare masterpiece every night.

iO began as ImprovOlympic before taking the shortened name. iO started in 1981 and has lived at verious venues before settling into its current home.

While the most popular shows here are in the $25-35 price range, you can find tickets for some performances as low as $5-10.

3 Annoyance Theatre

Neighborhood: Lakeview
Address: 851 W. Belmont Avenue, Floor 2
Price range: $5-15
Food and drink: Full bar
Popular shows: Trigger Happy: Magic Meets Improv, Co-Ed Prison Sluts
Notable alumni: Jane Lynch, Stephen Colbert, Aidy Bryant, Jeff Garlin, Amy Sedaris, Jason Sudeikis, Andy Richter, Vanessa Bayer

The Annoyance Theatre always has a bunch of creative shows running. This company has been producing shows for more than 35 years, including Shark Tank the Musical and The Real Live Brady Bunch.

Shows tend to be much cheaper here. Most nights, multiple shows run on the same stage, with crowds shuffled in and out between performances.

A recent favorite: Hitch Cocktails, an Albert Hitchcock-themed improv show and drinking game.

Like many small theaters, the Annoyance has a full bar waiting area.

annoyance theater Chicago comedy inside
Find great Chicago improv and comedy at the Annoyance Theatre.

Stephen Colbert started at Annoyance before moving on to Second City. Other Annoyance alumni include SNL stars Aidy Bryant, Jason Sudeikis, and Vanessa Bayer.

4 Neo-Futurist Theater

Neighborhood: Andersonville
Address: 5153 N. Ashland Avenue, Chicago IL
Price range: $20
Food and drink: None (you can bring your own snacks, but not alcohol)
Popular shows: Switchboard, The Infinite Wrench
Notable alumni: Spencer Kayden, Michael Cyril Creighton, Roberta Colindrez

Imagine getting to see 30 plays in one night. In one hour, in fact. That’s a lot of bang for your buck!

That’s the concept of shows at the Neo-Futurist Theater in Andersonville. For years, the longest-running show in Chicago was “Too Much Light Makes the Baby Go Blind,” created by the Neo-Futurists.

The show’s run ended in 2016, but the Neo-Futurist Theater now offers other weekend performances.

The showcase event is the Infinite Wrench, which has performances every Friday through Sunday. That’s your chance to catch 30 mini-stories all packed into one show!

5 Logan Square Improv

Neighborhood: Logan Square
Address: 2825 W. Diversey Avenue, Chicago IL
Price range: $5
Food and drink: None (BYOB is allowed)
Popular shows: The Saturday Show, The New Team Show

Logan Square Improv is a non-profit improv theater in the awesome neighborhood of Logan Square, my former home in Chicago.

This place often has $5 shows, featuring developing performers and folks enrolled in the center’s classes presenting improv and sketch comedy. It’s one of the best values in Chicago comedy.

What’s it Like to See Improv in Person?

My introduction to Chicago improv was a show called Felt, featuring puppets that use foul language and adult innuendos. Its mature comedy themes are not exactly Sesame Street. But it’s hilarious.

The show used to run for years at iO! Theater, but is now on hiatus, with occasional shows at random venues announced via Instagram.

felt theater chicago improv comedy

Like many improv shows, Felt relied on audience suggestions. Performers would occasionally ask the audience for a topic idea, and they would instantly begin weaving that topic into the show.

If you go to an improv show, arrive on time so everyone can be seated before the show starts. Expect to be seated tightly together in a small, packed room.

Most improv shows are fairly brief, about an hour or so. That’s a good length of time to provide sufficient entertainment, while allowing you plenty of time to do other things with your night.

The most popular shows and venues tend to cost more, while newer and less-established shows can be found for cheaper prices.

Many improv shows are all-ages, while others may be adults-only or 21+. Check the listing for the specific show you are interested in.

Chicago Comedy Events and Festivals

Some of the city’s best comedy-related festivals take place during the winter. The Chicago Comedy Film Festival runs in November.

The Chicago Sketch Comedy Festival is right in the middle of January. In February comes Chicago Theatre Week, and in early April, just as the winter weather starts to fade, is the Chicago Improv Festival.

A lot of these venues are near the Uptown area, which means you’re very close to other attractions, such as the legendary jazz club The Green Mill.

Improv and comedy are some of the best things to do in the Windy City during the winter.

What About Standup Comedy?

This article focuses more on improv and sketch comedy than standup. But if you’re looking for old-fashioned joke telling, check out venues like the Laugh Factory, Lincoln Lodge, Up Comedy Club, Comedy Clubhouse, and Zanies.

For more Chicago comedy details, check out this post from Choose Chicago.

Where to Get Cheap Tickets for Shows in Chicago

It took me a while to discover Chicago’s equivalent of the TKTS booths in NYC that sell last-minute theater tickets at big discounts.

The place to go in the Windy City to get half-price (or better) theater deals is Hot Tix, which has seats for a lot of the small, affordable Chicago improv comedy shows and some of the big Broadway-style stuff.

Hot Tix tickets can be purchased online, but you’ll have to pay the Ticketmaster surcharges, so your best bet is to head to their box office location: 108 N. State Street, located downtown in Block 37 Shops on State.

The box office is open from 10 am to 6 pm everyday, except 11 am to 5 pm on Sunday.

Fyi, you’ll still be hit with a service fee when paying in person at the Hot Tix outlets, but it’s less than the Ticketmaster surcharge.

And while you’re in town, don’t forget to check out some of Chicago’s best museums and that iconic Chicago food.

Do you have a Chicago improv or sketch comedy favorite venue?