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The 10 best comedy series in Chicago for fall 2023


This is quickly turning into a major embarrassment of riches when you start dissecting the upcoming fall comedy season. We apologize in advance to all the valued actors and artists not included in this list, from Second City to Laugh Factory. To be as fair as possible, let’s skip over some of the names on last year’s list, including Ron Funches and Maria Bamford, who have shows at The Den this fall (September 15-16 and October 26-28, respectively). and Chelsea Handler, who stops by the Chicago Theater on October 27-28.

As always, the fall will feature plenty of local talent, including the inaugural 312 Comedy Festival, which kicks off on October 27th. It also offers opportunities to catch some high-profile acts, some on rare tours — Iliza Shlesinger’s stop (Sept. 8) at the Chicago Theater is sold out; Demand for Dave Chappelle’s self-titled national tour is high enough to add a third night at the United Center (Oct. 4, 6 and 7).

This list could be 50 comedians long and still not be enough, but here are 10 comedians with Chicago dates popping up. .

Nikki Glaser: Nikki Glaser isn’t afraid to overshare. Maybe that’s what the title of the 2022 HBO special “Good Clean Filth” suggests, but get ready for lust when Glaser takes the stage. No topic is off-limits as she brings her open-book style to Chicago for one night on her “Good Girl” tour. 7 p.m. Sept. 15, Chicago Theatre, 175 N. State St.; nikkiglaser.com

DL Hughley: You probably know Hughley’s name, whether you’re watching him perform in “The Original Kings of Comedy” alongside Bernie Mac, Steve Harvey and Cedric the Entertainer, or watching him star in his own sitcom, “The Hughleys.” The Peabody Award winner, who spent three nights in Schaumburg, is known for topical comedy that features the latest headlines. 19:00 and 21:30 September 15-17 at Chicago Improv, 5 Woodfield Road, Woodfield Shopping Center, Schaumburg; improv.com/chicago

Anthony Jeselnik: Dark material? Certainly. The Los Angeles-based comedian will bring his Bones and All Tour to the Chicago Theater later this month. 7 p.m. Sept. 22, Chicago Theatre, 175 N. State St.; www.msg.com

Ben Schwartz and Friends: The “Parks and Recreation” star, known for his character Jean-Ralphio, is coming to Chicago with a team of talented improvisers from Los Angeles. The show is different every night, as every improv should be, so his one-night stay in Chicago is shaping up to be one of those “you had to be there” moments. 8 p.m. Oct. 7, Chicago Theatre, 175 N. State St.; rejectedjokes.com

Gabriel Iglesias: The last time “Fluffy” came to the United Center, its tour faced pandemic delays and rescheduling. This time, fingers crossed, the date for the “Don’t Worry Be Fluffy” tour has been set. Expect Iglesias to combine his personal experience growing up Latino in America with his recent life events while reveling in his signature lovable nature. Oct. 26, 8 p.m. United Center, 1901 W. Madison St.; fluffyguy.com

They should be: As always the Den’s Heath Main Stage is packed with talented comedians. Along with Funches and Bamford, Michael Ian Black (October 1), Beth Stelling (October 6) and Esther Povitsky (October 20-21) are just a few of the names on the list. But how can we not highlight Ziwe, who embraces embarrassing and uncomfortable moments on her late-night show “Ziwe”? Ziwe never shy away from race and politics in America. Who knows what to expect from “The Black Friend Tour” and the comedian reciting the lyrics of Cardi B’s song “WAP” to Gloria Steinem. Nov. 3, 7:15 p.m. and 9:30 p.m., and Nov. 4, 7:15 p.m., at Heath Mainstage at the Den Theatre, 1331 N. Milwaukee Ave.; thedentheatre.com

Chicago is one of several tour stops for Jerry Seinfeld and Jim Gaffigan.

Jerry Seinfeld and Jim Gaffigan: Two top comedians touring together for the first time and only four tours in total? This is a rare opportunity for Chicago (and thankfully it’s already added second night). 7:30 p.m., Nov. 9-10, United Center, 1901 W. Madison St.; unitedcenter.com/events

Jay Leno: A look at Hard Rock Live’s schedule shows it’s a tough choice between Leno and Tom Segura (October 14), but the former host of “The Tonight Show” has the advantage. Leno will bring his stand-up to the performance space at the Hard Rock Casino Northern Indiana for one night only. 7 p.m. November 11 Hard Rock Live, 5400 W. 29th Ave., Gary, Indiana; hardrockcasinonorthernindiana.com

Trevor Noah: The star-studded season at Chicago Theater continues with Trevor Noah’s “Off the Record” tour. The former host of “The Daily Show with Trevor Noah” will be ready to satirize the latest news when he takes the stage with his wit and sharp social commentary. 8 p.m. Nov. 13-16, Chicago Theatre, 175 N. State St.; trevornoah.com

Chris Tucker speaks on stage during Celebrity Fight Night XXV on March 23, 2019 in Phoenix.

Chris Tucker: The title says it all: “Legend Tour.” Tucker started doing stand-up before landing roles in the TV series “The Fifth Element” and “Rush Hour.” After a decade-long hiatus from stand-up, Tucker brings his high-energy comedy back to the stage, marking his first major North American tour since 2011. Nov. 29, 8 p.m., Chicago Theatre, 175 N. State St.; christucker.com

Jerald Pierce is a freelance writer.


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