Splitsider’s Guide to Chicago’s Comedy Scene

As any Chicago-based comedian, writer, or performer will tell you, there’s a glass ceiling everyone faces when developing a career in this city, due to the lack of an entertainment industry. Soon after a performer really begins to come into their own, firing on all cylinders (and sometimes before), they make the decision to move out to NYC or LA. It’s helpful to think of Chicago as a sort of comedy incubator, preparing comics for the big time.

That also means audiences regularly get to catch rising talent right before they hit, which makes Chicago’s comedy shows some of the scrappiest, most unique, and most reliably solid shows in the country. What the Chicago scene lacks in recognizable faces and TV credits is compensated for by a constantly evolving crop of innovative, hard-working performers at the top of their game, honing their craft before the imminent move.

Our recent exports include Saturday Night Live’s Aidy Bryant, Tim Robinson, and Cecily Strong, as well as Beth Stelling, who did a set on Conan just months after she relocated to Los Angeles, and Cameron Esposito, host of AST Records’ Put Your Hands Together, a comedy showcase/podcast that just took over Comedy Bang! Bang!’s recently vacated time slot at UCB LA.

When considering Chicago’s status as a comedy town, most folks think of the two sketch and improv institutions: Second City and iO. While these two venues are certainly thriving, underground, independently produced sketch, improv, and standup shows are finding success as well. This is by no means an exhaustive list, but we’ve compiled some of the best, longest running, and most unique shows from Chicago’s constantly growing standup, sketch, and improv scenes.

Best weekly shows

Arranged in chronological order, Mon.-Sun.

Armando Diaz Experience: The Armando Diaz Experience is one of the easiest ways to get to know the best improvisers at iO. Founded by Adam McKay, Dave Koechner and Armando Diaz, this rotating cast of the best improvisers at iO and a noteworthy monologist make for a memorable improvised experience. [OO]

Mondays, 8:30pm • $12 • iO, Lakeview

The Comedy Evening: Just shy of its one year anniversary, The Comedy Evening has quickly ascended to the upper tier of standup showcases in the city. Thanks to producer and host Dan Friesen, one of the scene’s biggest advocates (and founder of the recently-launched Nicest Guys In Town comedy network), TCE’s laid-back, friendly vibe gave Monday night its new scene favorite. [MB]

Mondays, 9pm • $5 suggested donation • The Ace Bar, Lincoln Park

Cook County Social Club:  Sometimes a group of improvisers transcends all modifiers and they are just damn good. Crazy energy, bizarre but endearing scenes, and an incredible devotion to “yes, and…” make this show more fun than most other improv shows in the city. [OO]

Tuesdays, 8pm • $12 • iO, Lakeview

Honorable mention: Potential Boyfriends

Chicago Underground Comedy: ChUC is a long-running standup showcase put up in the music room of the Beat Kitchen by a cast of some of the city’s most promising up-and-comers (former cast members include Nick Vatterott, Kumail Nanjiani, and Jared Logan). There’s always a chance of a surprise drop-in from more well-known performers when they’re in town, which makes ChUC one of the go-to spots for local comedy fans. [MB]

Tuesdays, 9:30pm • $5 • The Beat Kitchen, Roscoe Village

All Of It All The Time: Though still in its infancy, All Of It All Of The Time is one of the few weekly sketch showcases that features brand new material every week. This free show features a rotating cast of some of the more boundary-pushing performers in the city, all rallied around a unique theme or conceit that changes each week (a recent show required all sketch groups to perform without the assistance of lights of any kind). [MB]

Wednesdays, 8pm • Free • Chemically Imbalanced Theater, Lakeview

Comedians You Should Know: One of the highest-regarded standup shows in the city by performers and audience members alike, CYSK regularly sells out the back room of Timothy O’Tooles, a popular sports pub on the city’s Near North Side. The producers’ reverence for the art of standup and endless drive makes it easy to see why this showcase, now in its sixth year, is a scene favorite. [MB]

Wednesdays, 8pm • $5 presale/ $10 at the door • Timothy O’Toole’s, River North

TJ & Dave: You can also see TJ & Dave in New York, but it’s best to see these improv legends in their native Chicago. Good improv is normally amazing, but the intense bond and talent that these two bring to the stage is something to be experienced, especially if you’re a student of improv. [OO]

Wednesdays, 11pm • $5 • iO, Lakeview

Honorable mention:Felt

Stand Up Stand Up: The care put into the promotion of a standup showcase is often the difference maker in the success of a given room. That and the quality of the talent and the venue itself, of course – and the producers behind SUSU have hit the mark on all three counts. The unique, reliably goofy posters and consistently solid lineups in the trendy basement lounge of The Crocodile in Wicker Park means a memorable show for all involved. [MB]

Thursdays, 9pm • Free • The Crocodile, Wicker Park

Messing With A Friend: Chicago improv icon Susan Messing’s weekly show at the Annoyance pairs her up with a different “friend” each week for the best two-person improv show this side of TJ & Dave. Messing’s charmingly anarchic personality and fabulous taste in scene partners makes each show memorable and unique. [MB]

Thursdays, 10:30pm • $5 • The Annoyance, Uptown

The Lincoln Lodge: The wood paneled banquet room of The Lincoln Restaurant, a pancake house in Chicago’s North Center neighborhood, doubles as the home of the nation’s longest-running independent standup showcase. The Lodge’s DIY charm never overshadows how well this room is run, thanks to the ever-evolving cast of some of the scene’s weirdest and most exciting performers coupled with cofounder Mark Geary’s devotion to the scene. [MB]

Fridays, 9pm • $10 • The Lincoln Restaurant, North Center

The Improvised Shakespeare Company: Regular improv in itself can be difficult. But couple spontaneous two act plays with Shakespearean language, movement, themes and couplets and you have a show unlike any other in the city. This show sells out quickly each week, but it’s easy to see why. Not many people can do this so well and make it so fun. [OO]

Fridays, 8pm and 10:30pm • $16 • iO, Lakeview

Holy Fuck Comedy Hour: This loosey-goosey midnight show features comedic material written in a week’s time without the benefit of rehearsals from a cast of ringers from the city’s sketch and improv scene. Think of it as a sort of best-case-scenario open mic where talented, funny performers try out rough, silly sketches to a game audience. [MB]

Fridays, Midnight • Free • The Annoyance, Uptown

The Two-Hour Comedy Hour: A free, overstuffed standup showcase is a great way to kick off a Saturday night in Bucktown. As a means of keeping audience members engaged throughout the show, hosts and co-producers Andy Fleming, Emily Lake, and Katie McVay throw in participatory games like movie trivia and raffle off the chance to perform a special 42 second set onstage. [MB]

Saturdays, 7pm • Free • Gallery Cabaret, Bucktown

The Deltones: Stacked with the best improvisers at iO, this musical improv ensemble is one of the best in the city. Each Saturday top talent sings their hearts out and performs scenes for sold out crowds. Musical improv can easily go south, but the talent, devotion and musical chops of the Deltones make the show well worth your time. [OO]

Saturdays, 8pm • $14 • iO, Lakeview

Honorable mentions: BYOT

Entertaining Julia: The intimate, divey Town Hall Pub is the perfect venue for this lively variety show hosted by the city’s only vaudeville-by-way-of-Boystown duo, The Puterbaugh Sisters. Each show blends standup, sketch, and music with a uniquely easygoing vibe. EJ’s devoted crowd of regulars and the hosts’ insidery yet accessible comedy make for a uniquely party-like atmosphere. [MB]

Sundays, 9:30pm • Free • Town Hall Pub, Lakeview

3033: Improv groups come and go every month or so at iO, but 3033 has been around for the better part of a decade and it’s apparent. Spend your Sunday nights watching these veterans create something from nothing (not counting years of experience and comedy). [OO]

Sundays, 10:30 pm • $5 • iO, Lakeview

Honorable mention: Super Human

Best Monthly and Irregular Shows:

Kind of Blue: The Hideout is one of the city’s best rock clubs, so it’s no big surprise that it’s also a great place to see comedy. This monthly show regularly features some of the strongest lineups of local comedians, anchored by a bearded trio of likable producers. [MB]

First Sunday of every month, 7pm • $5 • The Hideout, Noble Square

Performance Anxiety: Perhaps the only franchised standup show in the city, Chicago’s Performance Anxiety stems from a showcase at the Pleasure Chest in Los Angeles. Last summer, former Chicagoan T.J. Miller passed the torch to a group of up and coming local standups eager to help make the show a beacon of sex-positive comedy both here and in Lipstick City. [MB]

Third Monday of every month, 8pm • Free • The Pleasure Chest, Lakeview

Kill All Comedy: On any given night, chances are that there’s a Kill All Comedy-affiliated sketch show going on somewhere around town. This collective of some of the city’s most exciting up-and-coming sketch performers rolls 20+ deep, many of whom perform at their monthly cast showcases at the Upstairs Gallery on the first Wednesday of each month, and at the biweekly standup/sketch showcase Kill All Comedy West at Quencher’s in Logan Square. [MB]

First Wednesday of every month, 8pm • Free • The Upstairs Gallery, Andersonville

Every other Monday, 8pm • Free • Quencher’s, Logan Square

Making Out with Wes Perry and Friends: Wes Perry, a talented singer, comedian, and writer, curates this monthly show with some of Chicago’s funniest, edgiest, and rawest talent. You don’t really know what to expect, but know that you’ll probably see something unlike any other variety show – whether it’s comedy, dance, poetry, stories, improv, burlesque, or whatever else can be done on a stage. [OO]

Third Wednesday of every month, 8pm • Free • The Upstairs Gallery, Andersonville

Finish Your Dinner with Oh Theodora & Drew’s Tumbler: After finishing a two year run of Show Theodora in December, Oh Theodora is moving with the Public House Theatre to the new permanent location in Wrigleyville. Each month these smart sketch groups write new dumb, absurd material. While no longer a variety show format, Oh Theodora and Drew’s Tumbler are a perfect match for each other and they won’t disappoint. [OO]

First Thursday of every month • $8 • Public House Theatre, Wrigleyville

Shame That Tune: The Chicago comedy scene has more than just comedians – there are also musicians. In the monthly music “game show”, three contestants come on stage, spin a wheel to determine the genre of an unwritten-song, tell embarrassing anecdotes, after which co-host Brian Costello interviews them about it, and co-host Ambraham Levitan unveils his extemporaneous song about the story. Got all that? Just see this show. [OO]

Monthly • $5 • The Hideout, Noble Square

Creative Control: The last Friday of every month, Saki hosts this incredibly fun stand up showcase. Up and coming Chicago standups do quick sets hosted by the Late Live Show’s Joe McAdam and a local band closes out the night. Also, there’s free beer from local brewers. To reiterate: a free show, with free comedy, free music, free beer, and a great time. [OO]

Final Friday of every month, 8pm • Free • Saki, Logan Square

The Late Live Show: Since its launch in 2010, The Late Live Show has transitioned from underdog to institution. After its tenure at Second City came to an abrupt end in the middle of its third season, the show has been featured at several comedy festivals and will soon begin its sixth (and final) season at the legendary iO theater. While they regularly pull exciting guests, (Community’s Danny Pudi, the WWE’s Victoria, A.V. Club head writer Nathan Rabin are a few highlights), what sets Late Live apart is the strength of its writers. Each week’s monologue is arguably stronger than most seen on late night TV, and some of the best, dumbest sketches in the city are peppered between more straightforward guest segments. [MB]

Saturdays at Midnight until 5/11/13 • $5 • iO, Lakeview

Collectors’ Edition: Local comedians Conor Sullivan, Sean Rose and Rick Joyce put together this monthly music essay show about their love for music and pop culture. Recent topics include Prince’s weird years, 90s alt rock radio, and pop culture scape goats. Get to know why these guys love music so much and why you should too. [OO]

Every other month, 8pm • Free • The Upstairs Gallery, Andersonville


iO: Del Close and Charna Halpern’s small Wrigleyville theatre is basically Mecca for improv nerds. Many of the greats and most Chicago improvisers either train or perform weekly on one of the two stages. If you noticed up above, most of the best improv can be seen here throughout the week. It’s well worth it to make it to a few shows if you can. If that’s not enough, iO’s well known alumni often stop by to perform when they’re in town. [OO]

Second City: Second City is synonymous with Chicago and comedy – and rightfully so. Several stages and a training center that boasts an impressive list of alumni (basically a majority of SNL since 1975) make this historic Chicago theatre a stop for tourists, Chicagoans and comedians on their way to stardom. The Piper’s Alley complex hosts a number of stages for Second City:

  • Up - A recent addition to Second City with a focus on stand up.
  • Donny’s Skybox - A stage for students of the Training Center to show off their newly acquired improv and sketch skills.
  • deMaat Theater - A newer addition to the Piper’s Alley complex for more experimental sketch shows from some of Second City’s up and coming talent.
  • E.T.C. - Basically another main stage with some great talent and shows.
  • Main Stage - You’ll see Second City’s current review here. Lots of important people have performed on this stage. [OO]
  • The Upstairs Gallery: The Gallery is one of hottest venues in Chicago comedy, hosting pay-what-you-can improv and sketch shows nearly every night of the week. While experience levels vary on some lineups – especially early on in the week – the Gallery’s cozy, welcoming vibe and penchant for experimental, genre-bending comedy make it an asset for the city’s writers and performers and those who love them. [MB]

    Lincoln Hall/Schubas: Once every few months, the folks behind Lincoln Hall and Schubas Tavern host nationally touring comics like Todd Barry, Hannibal Buress, and Jon Benjamin at one of their usually music-focused venues. These two venues are great spaces for comedy, especially Schubas – the smaller, tighter of the two rooms. [MB]

    The Annoyance Theatre & Bar: The dark red walls full of freaky clown paintings may seem unwelcoming to those not already familiar with the scene, but the Annoyance was founded by members of the Chicago comedy scene for their friends. The shows are generally not family friend (Coed Prison Sluts), experimental in nature (Holy Fuck), or simply bizarre fun. While it’s no longer simply an alternative to Second City and iO, but more of a mainstay of the Chicago comedy scene, the Annoyance is a great place to see what Chicago improvers and sketch comedians will do with very few boundaries. [OO]

    Jokes and Notes: Veteran comedian club owner Mary Lindsey opened this Southside comedy club in 2006, eight years after her previous club All Jokes Aside closed. Jokes and Notes is not just a continuation of the incredible scene that Lindsey helped incubate in the 90s, but a whole new space for black comedians and anyone else who can tell a good joke. As the only major comedy club on the South side, you can expect some national talent to come through, but watch out for the locals on Wednesdays and Thursdays, too. [OO]

    Zanies: An old-school comedy club for better (the walls are lined with headshots they’ve accumulated since their open in 1978) and worse (the two drink minimum plus an average $25 ticket price makes it hard to keep the evening’s price tag below $50 a head), Zanies is the only club in Chicago that survived the rocky years since the 1980s comedy boom. Though often attracting the sort of road dogs that might not appeal to Splitsider readers, Zanies does occasionally book modern underground favorites like James Adomian, Doug Benson, and Jimmy Pardo. [MB]

    Training and Classes

    Feminine Comique: Founded by former Chicagoan and current Put Your Hands Together host Cameron Esposito, The Feminine Comique offers aspiring female standup comedians the necessary tools to start their standup career. The class curriculum offers students the chance to learn comedy basics like persona development, confidence, and joke writing in a wholly supportive environment. [MB]

    iO: iO’s impressive alumni may convince you to train here, but the curriculum can be tough. After it all, you can enjoy a 6 week run in the Del Close Theatre with a possibility to try out for a regular show. If improv doesn’t interest you, iO offers some excellent writing classes. [OO]

    Comedy Studies: This academic collaboration between Second City and Columbia College, which was the subject of a comprehensive profile on this very site, was recently upgraded from a semester-long program to a full on bachelor’s degree program. Comedy nerds fresh out of high school now have the opportunity to pursue a “degree in theater with a concentration on comedy writing and performing” in a program unlike any other in the world. [MB]

    Second City Training Center: The Second City Training Center is probably the most well regarded improv comedy school in the world if you rank those sort of things. And they offer more than just improv classes. Musicians, writers, directors, and actors can all learn from the years of experience in Piper’s Alley. Classes range from two week intensives to full on bachelor’s degrees (see: Comedy Studies). [OO]

    Open Mic Nights

    Rathskellar: Lotties, a neighborhood bar in Wicker Park, hosts the Rathskellar open mic each Tuesday night. It’s well known among standups as a reliably solid spot. The show’s low-lit, moderately upscale basement setting lends it a certain classiness that most mics can’t touch, even as performers work out their latest batch of poop jokes onstage. [MB]

    Tuesdays, 9pm • Free • Lottie’s Pub, Wicker Park

    Wylin Out Wednesdays: Jokes & Notes offers one of the only weekly open mic nights on the South Side. Hosted by Marvin “M Dubs” Phipps, Wylin Out Wednesdays features a huge number of comics of every experience level from all over Chicago. [MB]

    Wednesdays, 8pm • $5 • Jokes and Notes, Bronzeville

    Cole’s: Shortly after its inception in 2009, the Wednesday night open mic at Cole’s in Logan Square became one of few must-do open mics in the city for up-and-comers and established standup comics alike. The show’s positive atmosphere and hip locale makes it one of the few mics in the city that regularly has a substantial number of non-comics in the audience. [MB]

    Wednesdays, 9pm • Free • Cole’s, Logan Square

    Two Black Dudes And An Open Microphone: Will Miles and Clark Jones are the titular two black dudes that host this monthly open mic at the always excellent Town Hall Pub on the final Tuesday of every month for over four years. The pair of producers pride themselves in running a show that feels more like a showcase than an open mic. [MB]

    Last Tuesday of every month, 9pm • Free • Town Hall Pub, Lakeview

    BYOT: Standups have it easy with all of their open mic nights, but iO’s Bring Your Own Team lets improv teams and sketch groups have their very own. Put your team name in the bucket and get called for 10 minutes, or 5 minutes if you’re doing sketch. Either way, up and coming improvisers and sketch comedians finally have a great way to show off what they’ve been working on. [OO]

    Saturdays at Midnight • $5 • iO, Lakeview

    Three Dead Moose: One of the most beloved open mics amongst the current crop of fledgling stand up comics, 3DM has a dedicated following of regulars, one of whom is tasked with live tweeting/lovingly Twitter roasting the performers each week (follow along each Sunday with the hashtag #3DM).  [MB]

    Sundays, 8pm • Free • Will’s Northwoods Inn, Lakeview


    SketchFest: Chicago’s own SketchFest started in January 2002 and has grown extraordinarily since then. Each January, hundreds of performers flock to Stage 773 to perform 30 minute sets. Never before in Chicago has it been so easy to see so much sketch comedy in one place over a few weeks. Chicago SketchFest has lots of local flavor with a few national acts and it’s a welcome variety of sketch in a city so focused on improv and stand up. [OO]

    Just For Laughs: Though Chicago’s second city status feels well-deserved at times, Just For Laughs helps Chicago-based comedy fans imagine what it’d be like if the city was a true-blue industry town. Boatloads of standup both national and local, as well as podcast tapings, improv sets peppered with famous folks, and special hour-long showcase spots given to a select few local performers, make for a very fun, very overstuffed week of comedy in Chicago. [MB]


    Local filmmakers are lucky to have such a deep well of talented writers and performers to collaborate with on various web shorts and series. Ted Tremper, an improviser and filmmaker, captures the intangible magic of expertly performed improv in his pair of web series, Breakups and Shrink, the latter of which was selected to run as a part of the New York Television Festival. Mark Colomb’s work with local improv and sketch performers like Conner O’Malley, The Shock T’s, and other Upstairs Gallery regulars on shorts like Fleetwood Mac Men showcases the strength of the scene as a whole (as well as Colomb’s skills as a filmmaker).

    The aforementioned Kill All Comedy regularly releases videos as well, the best of which often feature John Reynolds (who may be the heir to Steve Brule’s mushmouthed throne). Shorts like Dadz and World’s Best Burger are undeniable in their polished silliness. Joe Avella wrote and directed Master of Inventions, a remarkable feature length film produced on a Kickstarter-sourced budget of less than $2,000. Videos from the sketch and improv gals behind The Katydids have been featured all over the internet, and their ongoing web series Teachers recently joined forces with The Onion, which relocated to Chicago last year. Since that relocation, many Chicago-based writers and comics, including Cullen Crawford, Daniel Kibblesmith, and David Sidorov, have began contributing to the Onion News Network, whose daily videos are often transcendent in their absurdity and darkness. [MB]


    While Chicago’s not short on talented, ambitious performers, the podcast scene (unfortunately) often mirrors the relative inexperience of many of the people involved. A lot of shows start out strong with a regular release schedule and audio quality that’s at least tolerable, before dropping off after six months (sometimes less). Among the shows that have not fallen victim to this recurring issue, there are a few gems. The musically-minded Revolutions Per Minute features local comics Joe McAdam and Nick Rouley discussing artists and playing songs based around a new theme each episode. The pair’s shared love for music and dick jokes make for an enjoyable listen. The similarly niche-y Naked Sports Live is a sports-themed talk show recorded live twice a week by Chicago-based standups Megan Gailey and Joe Kilgallon, who share  their own personal sports-related stories and perspectives on the latest in sports news.

    Late last year, the Improv Nerd podcast joined the Feral Audio podcast network, giving it an incremental jump in cred that few other local shows can boast. Improv Nerd finds former Chicago Public Radio host Jimmy Carrane interviewing, and sometimes performing with, various luminaries from the Chicago (and national) improv scene, like Matt Besser, Charna Halpern, and T.J. Jagodowski. Other shows worth checking out include Friesen Point, Wrestling With Depression, The Standup Mixtape, and the recently shuttered Poor Choices Show. [MB]

    Things to bookmark

    For whatever reason, Chicago comedy is lacking in the independent online resources category. The home pages for iO and Second City offer well-maintained bios and dates for their many performers, as well as up-to-date show information. In the self-promotional department, I maintain a blog called The Steamroller, which features interviews with and creative content from many talented Chicagoans. Earlier this year, two Steamroller features, one from C.J. Toledano, and one from Joe Kwaczala, went viral, to the delight of all involved. The comprehensive list of showcases and open mics on Comedy of Chicago is a well-maintained resource for those in search of Chicago standup. They also occasionally feature interesting submissions from local performers covering the ins and outs of the scene. [MB]

    Photo by Ian Freimuth

    Owen O’Riordan is a freelance copywriter comedy fan from the suburbs of Chicago. You can see some of his other work here and follow him on Twitter.

    Matt Byrne is a freelance writer living in Chicago, you can follow him on Twitter here and should read The Steamroller, his blog all about the Chicago comedy scene.

    Check out our other local guides:

    -Splitsider’s Guide to NYC’s Comedy Scene

    -Splitsider’s Guide to LA’s Comedy Scene

    -Splitsider’s Guide to Boston’s Comedy Scene

    -Splitsider’s Guide to Austin’s Comedy Scene

    Splitsider’s Guide to Chicago’s Comedy Scene