Head to Chicago's Best Comedy Theaters & Shows for a Laugh After This Long Week

iO Theater Chicago stand up comedy sketch improv
Doug Roberts/Courtesy of iO Chicago

Chicago’s the city where improv comedy was created and cultivated, so it’s only fitting that today it serves as America’s incubator for up and coming comedic talent. With sketch, stand-up, and improv shows here every night of the week, it’s no easy task sorting through the litany of theaters and showcases around town. You might even say trying to narrow down the list of Chicago’s comic venues to the 22 best ones would be laughable... [pause for groans].  We’ve done it regardless, see one or see all, just don’t wear yourself out.

Second City Theater Chicago improv stand up sketch
The Second City 

The trusty standbys

The Second City & UP Comedy Club

Old Town

Safe to say the company that sparked the careers of national treasures like Bill Murray, Tina Fey, Stephen Colbert, Key & Peele, and countless others is pretty legendary. You can’t go wrong with tickets to the two-act sketch revues on either the Mainstage or ETC (buy in advance though), and UP draws a nice mix of comedians hitting their prime, like Pete Holmes, TJ Miller, and Amy Schumer.

iO Chicago
TJ and Dave

iO Chicago

Lincoln Park

Some call it the mecca of improv comedy (just don’t call it Improv Olympic™) because it’s where long-form improv took shape and continues to be an influence worldwide. Performances by Revolver and The Improvised Shakespeare Company are required viewing. Make it a point to catch a Wednesday night set from master improvisers TJ & Dave, who spin hour-long shows with no scripting at all that are equal parts hysterical and heartfelt.

Trigger Happy
Trigger Happy

The Annoyance Theater


Known for its dark and assertive tone -- no other theater could pull off shows like Skinprov or Holy Fuck Comedy Hour -- The Annoyance is home to at least a dozen must-see shows any given week. Having settled into its new Lakeview digs with two stages and a friendly bar, plan to be thrilled/shocked by the absurd, uncensored, and sharp wit from an ever-growing list of exciting performers.

Zanies Comedy Club Chicago
Zanies Comedy Club Chicago

Zanies Comedy Club

Old Town

Zanies has history. It’s one of the oldest continually operating clubs in the country (the website design can attest to that), and continues to offer a stacked list of touring comedians every night of the week. Be on the lookout for a hometown hero like Hannibal Buress to stop in. This is an old-school comedy club at its very best.

Jokes and notes Chicago comedy club improv stand up

Jokes and Notes


Jam-packed with nationally touring stand-ups and exceptional Chicago talents, Jokes and Notes delivers a steady stream of laughter to Chicago’s South Side. Owner Mary Lindsey has had a hand in bringing up acts like Chris Rock, Dave Chappelle, and Mo'Nique, so don’t miss an opportunity to see who’s coming up next.

Comedy Sportz Theater comedy improv sketch
CSz Theather Chicago

ComedySportz Theater


If you’ve been known to binge-watch episodes of Whose Line is it Anyway? you’ll feel right at home in Chicago’s home of short-form comedy. Since 1987, ComedySportz has slickly combined elements of athletic competition, empty-headed humor, and terrible/incredible puns into an exciting and engaging family-friendly show.

Stage 773 Chicago comedy improv sketch club
Michael Courier Photography

Go-to sketch and improv theaters

Stage 773


Stage 773 is comedy festival central, playing host to the massive Chicago Sketch Comedy Festival as well as the Chicago Women’s Funny Festival and Chicago Nerd Comedy Festival. Throw in the city’s longest-running musical comedy, Cupid Has a Heart On, and a batch of other independently produced showcases, and you’ve got yourself an easy go-to option for comedic entertainment.

Public House Theatre Chicago comedy
Byron Hatfield

The Public House Theater


Chicago is full of comedy shows where the jokes are brought out to the bars. The Public House Theater, however, flips that 180 degrees and provides a casual bar atmosphere to two professional stages. In fact, many of the theater’s offerings include a free drink in the ticket price, giving you a head start for its marquee show, Bye Bye Liver: The Chicago Drinking Play.

The Neo-Futurists Chicago comedy club
Joe Mazza at Brave Lux

The Neo-Futurists


The Neo-Futurists have been writing and performing new material every week since 1988 in an attempt to perform 30 plays in 60 minutes for their flagship show, Too Much Light Makes The Baby Go Blind. Every night is a gamble (a good gamble): rolling dice to set your ticket price, getting to share a pizza with the whole crowd if they sell out, and, of course, possibly never seeing the end of a play; for when the clock runs out, the show is over -- no matter what. Oh, and there’s always the possibility of nudity, contortionism, or something else you’ll have no clue how to adequately describe to your co-workers on Monday morning.

CIC Theater Pimprov chicago comedy
CIC Theater

CIC Theater


Among the growing crop of comedy venues in Lakeview, CIC is the underrated black box theater that delivers the same caliber of improv and variety of acts as its more mainstream counterparts. Check out the weekend house team nights, experimental sketch shows, and Pimprov (at least once for the gimmick).

Comedians You Should Know in Chicago, Illinois
Michael Sanchez

Independent stand-up and variety showcases to seek out

Comedians You Should Know</a> at <strong>Timothy O'Toole's</strong>

Gold Coast

On its face, CYSK may look like just another backroom bar mic being stationed in Timothy O'Toole’s Pub. But make no mistake, it’s one of the most highly regarded stand-up showcases in Chicago. You will see top-notch performances from the best local comics the city has to offer, along with the occasional drop-in set from larger national acts.

Lincoln Lodge Chicago Comedy comedians
Erin Nekervis


Wicker Park

It’s Chicago’s longest-running indie comedy showcase for good reason. Just check out the list of notable alumni. While Second City is the breeding ground for SNL’s top talents, The Lincoln Lodge is where headlining comedians find their voice, experimenting with characters, sketches, or bits that add more visual variety than “guy standing on stage holding microphone.”

Green Mill cocktail lounge chicago exterior sign
Flickr/Keith Cooper

The Green Mill


Billed as a “weekly live magazine,” each Saturday at 3pm, comedic performers, storytellers, and musicians descend upon the historic Green Mill to put on one hell of a variety show. Pull up a Capone booth seat early (the show is free and fills up), order a classy cocktail, and prepare to take in all the laughs from the week that was.

Chicago Comedy Underground stand up comedian
Luis Cardenas

Beat Kitchen

Roscoe Village

Serving up a rotating cast of some of Chicago’s best up-and-coming stand-ups paired with local drafts and lamb lollipops, ChUC -- as it’s affectionately referred to -- is a warm room for cool bits.

Flat Iron comedy Chicago Collaboraction Theater
Courtesy of Flat Iron Comedy

Flat Iron Comedy

Wicker Park

Navigate your way through the halls of the historic Flat Iron Arts Building to the Salon at Collaboraction Theatre and you’ll find yourself inside an excitingly intimate alt-comedy venue. Here, character is king and shows give a fresh breath of diversity. Look for the Tuesday and Wednesday night variety showcases and Wes Perry’s No Boys Allowed on Saturdays.

Congrats On Your Success Comedy chicago
Charlie Rohrer

Uncharted Books

Logan Square

This monthly comedy showcase stacks up among the best. Used books + fresh humor x all the beer you can bring = great success.

The Shithole improv Chicago
Jim Vondruska/Thrillist

The Shit Hole

Various locations

The Shit Hole’s roving artistic playground has grown from a fledgling underground show to an experimental pillar of Chicago’s comedy community. An incredibly inviting show under the guise of a secret society, The Shit Hole maintains a nomadic status with an ever-growing list of undisclosed spaces (music venues, garages, a museum?!) all over the city -- only announcing show locations on the day of. The path to finding the show involves training via the kumite and messaging via social media for details.

Yeah buddy awesome time comedy chicago
Blake Burkhart

Brainstorm Comics

Wicker Park

Cream of the crop when it comes to alternative stand-up spaces, slip inside this free show packed with nerdy enthusiasm and charming up-and-comers.

The WIP Theater Chicago
Jessica R. Avila

The WIP Theater

Edison Park

The WIP has garnered a reputation for taking great care of patrons in its quaint club, showcasing a great mix of touring stand-up acts and local favorites. BYOB for now, though they plan on finishing construction on their bar early in 2016. So hurry if you like to drink on the cheap.

The Revival Chicago comedy
Elizabeth Ryder

Newcomers to the scene

The Revival

Hyde Park

The Revival brings improvisational comedy back to Hyde Park -- where it originated from the University of Chicago intellectuals in 1955 -- with a gorgeous new space and a lineup of diverse and talented ensembles and comics from across the city.

Laugh Out Loud theatre
Courtesy of Laugh Out Loud Theater- Chicago

Laugh Out Loud Theater Chicago

North Center

Expanding upon its successful theater in Schaumburg, LOL brings its own twist to parlor-style improv comedy into the city. Featuring both family-friendly and anything-goes shows, bring the kids or a date, grab a cocktail from the antique bar, and sit back for two acts of laughs.

The Crowd Theater Chicago
The Crowd Theater

The Crowd Theater

Buena Park

While maybe not Chicago’s “only improv comedy theater” (though they claim to be), The Crowd is surely Chicago’s newest independent comedy theater. Stirring up the scene with an ego, attitude, and unrivaled support of its performers, this space is quickly rising among the ranks with tasty comedy options most every night of the week.

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Spencer Shore is a Thrillist contributor and avid comedy fan. His favorite joke is that one where the "blind man" isn't actually blind. Do you know it? How's it start?