The 13 best recurring comedy shows in Chicago

Mercury retrograde getting you down? Pick yourself back up and laugh about it with Astrobitch, Chicago’s new astrology-themed monthly comedy show at eclectic Irving Park venue Color Club. Host Ameerah Sanders (who’s an Aries, btw), curates a lineup of hilarious indie comics, all of whom have that month’s zodiac sign, except for one. It’s up to you to guess who’s the odd one out to win some prizes (like a tarot reading from Sanders), or you can just sit back and enjoy some great standup if you’re one of those people that thinks astrology is nonsense, which is exactly what a Capricorn would say. 

Last Friday of the month, 7:30pm, Color Club, 4146 N Elston Ave

If you’ve been following the comedy world in Chicago even marginally over the past decade, you probably know about Cole's open mic already. If you don’t, allow us to initiate you: back in the forever-ago of 2009, Coleman Brice, owner of the eponymous Logan Square watering hole, started an open mic with local scene stalwarts Chicago native Cameron Esposito (Take My Wife, Brooklyn Nine-Nine) and Adam Burke (Wait, Wait… Don’t Tell Me) as co-hosts. Years later, their legacy lives on, and if you can stay up that late on a school night, you can see as many as 40 comedians—some veterans, some trying standup for the very first time—get on the mic, all for the low, low price of free. 

Wednesdays, 9 pm, Cole’s Bar, 2338 N Milwaukee Ave

Come to an unassuming basement sports bar in Streeterville on Wednesday nights and get hit with an all-star roster of local talent. CYSK has been running since 2008 and in that time, has remained a top destination for checking out comedy talent. Try some of Timothy O’Toole’s wings and grab a pint and get ready to laugh.

Wednesdays, 8 pm, Timothy O’Toole’s, 622 N Fairbanks Ct

Second City is known for its sketch and improv, and with Dance Like There Are Black People Watching, you get all of that with an extra dose of “brilliant Black joy.” If you’re going to catch one show at the Second City complex right now, make it this critically-acclaimed revue-style show, which gives you all the sketch and improv you know and love, plus original songs and a whole lot more. 

Fridays & Saturdays, 8 pm, UP Comedy Club, 230 W North Ave

There’s something special about that sweet, sweet feeling of discovery when you stumble upon a new thing before the rest of your friends do. You can revel in that feeling once a month at Fresh Faces Chicago, the Laugh Factory’s monthly showcase focused on up-and-coming talent. Just remember, while it’s fun to be the first to discover your favorite new comic, good friends don’t gatekeep.

Last Tuesday of the month, 7:30 pm, Laugh Factory, 3175 N Broadway St

Zack and KiKi have been coworkers, roommates and best friends, and now, they produce a comedy storytelling show together about the highs and lows of friendship, from work-spouse drama to roommate shenanigans and everything else. Each show features two openers, an interview with special guests and a performance from the hosts. Grab your besties and make a date for this one—you may even be tempted to share your own wild stories.

Tuesdays, 9:30 pm, Annoyance Theatre, 851 W Belmont Ave

Do you enjoy Chicago’s thriving storytelling and live lit scene but just wish there were more stories involving bodily fluids? Then we’ve got great news for you—there’s Ladylike, a monthly showcase where women & non-binary comedians share their grossest and most personal stories. If you’re feeling especially brave, audience members can anonymously share their gross stories to be read in between acts. Not enough talk of bathroom emergencies and pilonidal cysts for you? Host Gena Gephart also runs the show’s podcast. 

Third Tuesday of the month, 8:30 pm, Lincoln Lodge, 2040 N Milwaukee Ave

If you love Chingona Comedy Hour, expand your horizons with Las Locas’ other show, Sabado Night Laughs, packed with comedians and special guests—one evening, a rep from Ascend Cannabis was even on hand to answer guests’ “burning” questions. 

First Thursday of the month, 8 pm, Laugh Factory, 3175 N Broadway St

Comedy aficionados love to wax poetic about how comedy speaks truth to power and holds a mirror up to society. But sometimes, you just gotta sit back and enjoy a heaping plate of raunch. At The Nasty Show, comics are encouraged to bring their darkest, dirtiest, most depraved, bluest-of-the-blue material. If that kind of humor is your thing, this show is a must-visit, but you may need a shower afterwards.

Saturdays, 11 pm, Laugh Factory, 3175 N Broadway St

“Noche de Risas” means “night of laughter,” and that’s exactly what you’ll get at this monthly showcase at laid-back Ravenswood neighborhood bar My Buddy’s. Actor and comedian Ruben “Baby Horchata” Ramirez hosts and curates the lineup, featuring local and nationally touring acts. Be sure to follow the show on Instagram for promo codes on tickets and occasional giveaways. 

First Fridays of the month, 8:30 pm, My Buddy’s, 4416 N Clark St

For seven years, Abi Sanchez (featured on Entre Nos on HBO Max) and Jaime DeLeon have been bringing Chicagoland’s best comedians to Simone’s in Pilsen. In addition to a diverse lineup of local staples and rising stars, you may get a surprise visit from a celebrity—Second City alum and former Saturday Night Live cast member Chris Redd dropped by in January 2020. Come for the laughs, stay for the food and drink specials and occasional opportunity to give back to the community—the hosts organized a coat drive for asylum seekers arriving in Chicago for their November show. 

Third Wednesday of the month, 8:30 pm, Simone’s, 960 W 18th St

Putting together a recurring comedy repertoire is tough. Putting together a standup repertoire and coming up with a compelling poem? A challenge for only the bravest (or most vulnerable) performers. At this intimate Wicker Park house of laughs, comedians follow each set with a poem about the same experience that inspired the jokes. Take your friend who prefers serious literature to stand-up and get them to lighten up a little. 

Thursdays, 10 pm, The Comedy Clubhouse, 1462 N Ashland Ave

Picture it: you’re at an open mic, and the comedian on stage is just starting to get into their groove. You get a few laughs, and then just like that, their set’s over. There are no tight fives at Stand Up Stand Up—at this showcase, which has been going strong for more than a decade, comics are given an ample 30-45 minute set to explore their material. Over the years, Stand Up Stand Up has welcomed a host of comedy heavy-hitters, including River Butcher and SNL’s Sarah Sherman. Come see the next great comedic voice before they inevitably move to New York or Los Angeles.

Wednesdays, 7:30 pm, The Den Theater, 1331 N Milwaukee Ave