10 Best Chicago Comedy Clubs: Stand-Up, Improv & Sketch Shows

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Looking for a side-splitting night of laughter in the Windy City? As a long-time Chicago resident and avid comedy fan, I can attest that our city’s vibrant comedy scene offers a smorgasbord of world-class venues to catch hilarious stand-up, improv, and sketch shows.

10 Must-See Chicago Comedy Clubs: Stand-Up, Improv & Sketch Laughs Guaranteed!

From legendary clubs that helped launch comedy giants to intimate theaters nurturing the next crop of talent, here are my top 10 picks for the best places to experience gut-busting comedy shows in Chicago.

Legendary Laughs: Historic Chicago Comedy Venues

Zanies Comedy Club (Old Town): Launching Careers for Decades

littlechicagoguide-comedy shows zanies — Zanies Old Town Exterior photo via Management

Zanies is a true Chicago institution that I always frequent for a good comedy show. This Old Town staple is renowned for hosting top-notch comedians in an intimate club setting that always delivers a great experience. Zanies has launched the careers of many famous funnymen and continues to be my go-to for catching the hottest rising talents.

The Chicago Theatre: Iconic Performances in a Historic Setting

Attending a high-profile comedy show at the legendary Chicago Theater is a true rite of passage for any humor enthusiast in the Windy City. This ornate, palatial venue exudes grandeur and elegance, from its decor to the impeccable acoustics. Witnessing world-renowned comedians command the iconic stage has left me in stitches time and time again, creating cherished memories that epitomize the unparalleled comedy experience Chicago has to offer.

Second City (Old Town): Launching Comedy Legends Since the 1950s

littlechicagoguide-comedy shows second city — Second City Interior photo via Management

No list of Chicago comedy venues would be complete without mentioning the legendary Second City. As someone obsessed with improv and sketch comedy, this celebrated club has been my mecca for years. It famously acted as a launchpad for comedy greats like Tina Fey, Stephen Colbert, and so many more over its storied history.

Rising Stars & Big Names: Catch Top Comedians in the Windy City

The Laugh Factory (Lakeview): Big Names & Fresh Faces

littlechicagoguide comedy shows laugh factory — Laugh Factory Chicago Interior photo via Management

This Lakeview comedy club has been one of my favorite spots to catch a show for years. The Laugh Factory draws big-name acts that never fail to sell out, but they also give the mic to up-and-comers showcasing fresh material. The vibrant atmosphere and reasonable prices make it a beloved destination for fans seeking outrageously funny comedy shows in Chicago.

Laugh Factory (Rosemont): Top Comedians Near O’Hare Airport

This massive comedy club located near O’Hare airport is a convenient option to catch top comedic talents when visiting or passing through Chicago.

From Improv to Sketch: Diverse Comedy Shows for Every Taste

iO Theater (Wrigleyville): Longform Improv at its Finest

littlechicagoguide comedy shows the io — The iO Theater Interior photo via Management

Any diehard fan of Chicago-style longform improv knows that the iO (formerly ImprovOlympic) is the place to be. As a longtime supporter, I’ve caught countless hilarious shows at this beloved Wrigleyville hub. With multiple stages and a top-notch training center, it’s the hot spot for the city’s best improv talent.

The Annoyance Theatre (Uptown): Bold & Experimental Comedy Shows

This gritty, boundary-pushing Uptown venue is home to bold, experimental comedy shows. Catch hilarious, offbeat productions from top improv and sketch groups.

Beyond the Big Names: Unforgettable Comedy Experiences in Chicago

Timothy O’Toole’s (Streeterville): Pub Fare & Side-Splitting Stand-Up

This Streeterville pub has been serving up pints and punchlines for years with side-splitting stand-up showcases nearly every night of the week

UP Comedy Club (Old Town): BYOB & Local Talent

UP Comedy Club’s intimate space and BYO policy make it a laid-back spot in Old Town to enjoy national touring acts and local stand-up talents.

The Den Theatre (Wicker Park): Nurturing Chicago’s Rising Stars

This multi-stage Wicker Park venue hosts a diverse array of touring comedians, comedy troupes, and offbeat shows with a focus on nurturing Chicago talent.

From historic venues like Second City to cutting-edge comedy clubs nurturing the next Tina Feys, Chicago’s incomparable scene offers endless laugh-out-loud entertainment. As a local who has been immersed in our city’s comedy world for years, I can’t recommend these top 10 spots enough for unforgettable comedy shows in Chicago that will have you rolling in the aisles. Trust me, you won’t regret checking out these world-class venues on your next visit!

EXPERT TIP: For all of your ticketing needs be sure to check the venues website or go through verified ticket sellers like ticketmaster.