Fall in Chicago Is Better With Live Comedy: The Best Comedy Shows to See This Fall
DERIC CAHILL
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JOSH THOMAS
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CHRISTINA P
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GABBY BRYAN
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THERAPY GECKO
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MARTIN AMINI
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JIM NORTON
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SHANNON FIEDLER
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DAVID KOECHNER
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RAYNA GREENBERG
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DERIC CAHILL | JOSH THOMAS | CHRISTINA P | GABBY BRYAN | THERAPY GECKO | MARTIN AMINI | JIM NORTON | SHANNON FIEDLER | DAVID KOECHNER | RAYNA GREENBERG |
Fall in Chicago Is Better With Live Comedy: The Best Comedy Shows to See This Fall
There’s something about fall in Chicago that makes the city feel brand new. Patio season turns into sweater weather, the leaves change across Chicago neighborhoods, and suddenly spending an evening inside with a drink and a great show sounds pretty perfect.
Whether you're planning a fall date night in Chicago, looking for weekend plans with friends, or searching for things to do in Chicago this fall, live comedy belongs on the list.
Located in the heart of Wicker Park, The Den Theatre welcomes nationally touring comedians, internet favorites, podcast stars, and some of stand-up's most exciting voices throughout the season.
Here are some of the best comedy shows coming to Chicago this fall.
Phil Hanley
Originally from Oshawa, Canada, Phil is now a key figure in the NYC comedy scene, performing regularly at the Comedy Cellar. With nearly 650K followers on Instagram and nearly 400K followers and 15.6 million likes on TikTok, he’s appeared on major late-night shows like The Tonight Show, Late Night with Seth Meyers, and The Late Late Show.
Joe Dombrowski
Recently named one of Variety’s Top 10 Comics to Watch, Detroit native Joe Dombrowski first caught the world’s attention in 2017 with a viral April Fools’ Day spelling test prank that led to multiple appearances on The Ellen DeGeneres Show. Don’t get it twisted, though—it takes 20 years to be an overnight sensation! Joe’s been performing stand-up since his third-grade talent show, and he hasn’t stopped since.
Vinny Guadagnino
Vinny Guadagnino is one of the most recognized lifestyle personalities and digital influencers. Vinny first rose to fame in 2009 on the MTV series “Jersey Shore,” which over its six-season run became the highest-rated series in the history of the network and a cultural phenomenon. During his time away from the shore, Vinny starred in series including “Vinny & Ma Eat America” on Food Network and “Joking Off” on MTV2. In April 2018, the franchise returned as “Jersey Shore: Family Vacation,” and immediately recaptured the zeitgeist, breaking viewership records along the way. The show’s 7th season premiered on February 8th, 2024.
Taylor Tomlinson
With 15 years of stand-up experience and four Netflix specials before the age of 32,Taylor Tomlinson has established herself as one of the most influential comediansof her generation. Her distinctive voice has earned widespread acclaim across the entertainment industry, with CNN declaring that audiences are in “the era of Taylor Tomlinson,” and Rolling Stone writing that she has, “conquered comedy." She has been inducted into Forbes 30 Under 30 and TIME100 Next, highlighted in Variety’s “10 Comics to Watch” and annual “ComedyImpact Report,” and named one of The Hollywood Reporter’s “100 Most Powerful Women in Hollywood.”
Catherine McCafferty
Catherine McCafferty is an actor, writer, comedian, and the host of viral digital series, PRETTY GAY, exclusivity on Patreon and produced by Sam Reich (DropOut TV) and Elaine Carroll (Very Mary-Kate). Catherine can be seen in the queer high school rom-com CRUSH on Hulu, as well as indie horror feature AMERICAN CARNAGE starring Jenna Ortega. Most recently, Catherine performed at the Edinburgh Fringe Festival where she debuted her hour of comedy: (Not) That Bad, garnering five four-star reviews and a nomination for the Birds of Paradise Best Emerging Artist award.
Ralph Barbosa
One of the shyest attention hogs to ever do comedy, Ralph Barbosa’s disarming and laid-back style has made him a stand-out on stage, on TV and as host of the Formula Bean YouTube channel with Luis Cisneros.
On August 8, Ralph premiered his second hour-long stand-up special, Ralph Barbosa: Planet Bosa, as part of Hulu’s new Hularious comedy brand. The special was shot in January at The Balboa Theatre in San Diego.
