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

Published On 03/03/2016 Published On 03/03/2016
iO Theater Chicago stand up comedy sketch improv
Doug Roberts/Courtesy of iO Chicago
The Second City 

The trusty standbys

The Second City & UP Comedy Club

Address and Info

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.

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

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

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


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.

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.

Michael Courier Photography

Go-to sketch and improv theaters

Stage 773

Address and Info


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.

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.

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

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).

Michael Sanchez

Independent stand-up and variety showcases to seek out

Comedians You Should Know at Timothy O'Toole's

Address and Info

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.

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.”

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.

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.

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.

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.

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.

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.

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.

Elizabeth Ryder

Newcomers to the scene

The Revival

Address and Info

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.

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

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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1. The Second City 1616 N Wells St, Chicago, IL 60614

If you've ever laughed, chances are you've laughed at someone that came out of The Second City. Alumni of this prestigious comedy school include John Belushi, Dan Aykroyd, and Tina Fey, among many, many others. If you want a career in comedy, train there. If you want a fun night out, catch one of their improv sketch comedy shows (for example: A Clown Car Named Desire), performed just about every night of the week.

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2. Annoyance Theatre & Bar 851 W Belmont Ave, Chicago, IL 60657

The Annoyance Theatre is the home of Chicago’s longest running musical, Coned Prison Sluts. Stop in for new and original plays, musicals, and sketch shows in a fun, uncensored atmosphere. Happy hour is between 5:30 and 7:30 Monday and Thursday. Annoyance also provides improv training classes focused on personal feedback and each student’s unique voice. The venue features three spaces: the bar, which holds 70 people, for an auditorium-style event; the small theater, holds up to 36 people, for small presentations or lectures; and the main stage theatre, 98 people, for catered events.

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3. iO Chicago 1501 N Kingsbury St, Chicago, IL 60642

iO (formerly known as ImprovOlympic) teaches classes on and hosts performances of improv comedy. Its main focus is on long-form improv (that's when a crew improvises for at least 25 minutes. In short-form, each skit is interrupted by audience suggestions or only plays out for a scene). The theater hosts several events daily, with famous guests and alumni popping in all the time.

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4. Zanies Comedy Club 1548 N Wells St, Chicago, IL 60610

Open for over 30 years, Zanies harkens back to golden days of Hollywood and comedy. Signed photos of A-list celebrities decorate the wall and the small, intimate club packs guests every night, which adds to the fun-time feel. Like most comedy clubs, there is a two drink minimum. Get ready for some deep belly laughs, just try not to fall out of your chair; someone does every show. Insider’s tip: if you sit in the front row, prepare to be in the show.

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5. Jokes And Notes 4651 S Dr. Martin Luther King Jr Dr., Chicago, IL 60653

Wednesday through Sunday evenings, Jokes and Notes on Chicago's Southside offers great comedic performances from a variety of performers and nightly drink specials. This lively, raucous, and feel-good space is perfect for date nights or casual night outs, offering gut-busting laughs and nightly drink specials. Be forewarned that this popular venue gets packed, and there's a two drink minimum. (Oh, twist my arm.)

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6. ComedySportz Theatre 929 W Belmont Ave, Chicago, IL 60657

ComedySportz host an all-improv show where a red and blue team compete for your laughs. A “referee” hosts the show, serving as a liaison between the audience and actors. After each game, scene or song, the audience decides the winner on the spot based on an applause-o-meter. The family-friendly show provides smart and (for the most part) clean comedy. The troupe often invites audience members on stage to join in on the fun.

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7. Stage 773 1225 W Belmont Ave, Chicago, IL 60657

Located in the Belmont Theatre District, Stage 773 is a performance and tenant venue providing entertainment on four stages. Shows include comedy, theatre, dance, and musical presentations (including burlesque!). The not-for-profit showcases established and up-and-coming artists alike. Check out its three annual events: The Chicago Sketch Comedy Festival, Women’s Funny Festival, and Nerd Comedy Festival.

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8. Public House Theatre 3914 N Clark St, Chicago, IL 60613

With an interior inspired by the old-time cabaret-style theaters, The Public House is provides a casual, dive-bar atmosphere for a super chill night out. Stop in and grab some drinks for one of their repeat, short-run shows, original scripted comedy, or 100% improv performances. The theatre is best known for their show "Bye Bye Liver: The Chicago Drinking Play," an interactive comedy drinking game. Four stars-- a must see.

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9. Neo-Futurists 5153 N Ashland Ave, Chicago, IL 60640

The Neo-Futurists boast the longest-running show in Chicago, “Too Much Light Makes the Baby Go Blind.” The signature late-night event, which had its first performance in the 80s, is a single 60 minute improv show where the troupe attempts to perform 30 plays with a rotating cast of characters. It is constantly reinvented and experimental, so no shows are ever alike, but are always awesome.

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10. CiC Theater 1422 W Irving Park Rd, Chicago, IL 60613

You’ll get the best bang for your buck here. Check out some grade-A comedy at Cic. Plus, parking’s free. The non-profit comedy theater produces improv, set and theatrical shows and has an in-house full service bar. Shows are performed Wednesday through Sunday.

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11. Timothy O'Toole's 622 N Fairbanks Ct, Chicago, IL 60611

TOT has everything you could want in a dive bar and more: billiards, classic bar food, 48 beers on tap and over 70 HD televisions. The menu offers wings and burger staples as well as healthy options and a children’s menu. Stop in on the weekend for brunch, featuring a Build Your Own Mimosa and Bloody Mary drink bar. This neighborhood pub hosts events such as trivia, karaoke, and comedy nights.

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12. Subterranean 2011 W North Ave, Chicago, IL 60647

Musicians, DJs, burlesque dancers, and even the longest-running indie comedy showcase—you name it. This bi-level, multi-faceted venue boasts a variety of acts alongside weekly drink specials and an extensive selection of bar food.

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13. Green Mill Cocktail Lounge 4802 N Broadway St, Chicago, IL 60640

Famed for being Al Capone's favorite bar during the heyday of Prohibition, Green Mill Cocktail Lounge is now known as one of the finest jazz clubs in the country. The Uptown bar hosts live performances every night of the week, and the acts range from contemporary jazz bands and quartets to swing orchestras and solo guitarists. The cover charge is usually between $4 and $15, depending on the band. Note: Green Mill is cash-only.

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14. Beat Kitchen 2100 W Belmont Ave, Chicago, IL 60618

In addition to serving creative fare—lamb lollipops, chorizo and goat cheese pizza—The Kitchen Beat also hosts local bands and weekly comedy shows. There is something for everyone here, whether you are a foodie, a comedy lover, or a supporter of local bands.

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15. Collaboraction Theatre Company 1579 N Milwaukee Ave Ste 336, Chicago, IL 60622

Hidden within the Flat Iron Arts Building you'll find an intimate alt-comedy venue, Flat Iron Comedy. Here you'll find diverse comedy acts and variety showcases every Tuesday and Wednesday. On Saturday you can see Wes Perry's No Boy Allowed.

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16. Uncharted Books 2620 N Milwaukee Ave, Chicago, IL 60647

First and foremost a hub for buying and selling used books, this Logan Square staple also regularly hosts a number of a live events, ranging from literary to comedic (be sure to check out "Congrats on Your Success," a monthly comedy showcase). Also a community space, Uncharted Books also encourages eating, drinking, and socializing.

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17. Brainstorm Comics 1579 N Milwaukee Ave #321, Chicago, IL 60622

Brainstorm Comics may not be the most main stream of comedy venues, but it is certainly one of the best. Head here to check out shows like the Yeah Buddy Awesome Time Comedy Show, pack with nerdy enthusiasm and totally free to see.

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18. The Wip Theater 6670 N Northwest Hwy, Chicago, IL 60631

When you think about comedy clubs, you rarely think about their customer service, but The WIP Theater is known for taking great care of their patrons. They like to feature a combination of local comedians and touring stand-up acts. Keep your eyes peeled cause they will be adding a bar to their venue very soon.

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19. The Revival 1160 E 55th St, Chicago, IL 60615

Searching for some great live entertainment in Hyde Park? Look no further than The Revival. Here you can see diverse and talented ensembles from all over Chicago in The Revival's gorgeous new space. This is a great place to visit whether you are a local or a wandering tourist.

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20. Laugh Out Loud Theater Chicago 3851 N Lincoln Ave, Chicago, IL 60613

The Laugh Out Loud Theater has something for everyone who stops by to see some parlor-style improv comedy. They have family-friendly shows and shows for adult audiences only, as well as an antique bar to grab cocktails from. If you are unsure of where to take a date or the family this weekend, consider stoping by Laugh Out Loud.

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21. The Crowd Theater 3935 N Broadway, Chicago, IL 60613

The Crowd Theater is one of the newest additions to Chicago's comedy scene, and while it may not be the only improv theater in town, it is certainly one of the best. If you are a big fan of live comedy and are looking for something new to experience, The Crowd Theater should be one your list of places to visit.