Summer in Chicago Isn't Complete Without Live Comedy: The Best Comedy Shows to See This Summer

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 |

Summer in Chicago Isn't Complete Without Live Comedy

There’s nothing quite like summer in Chicago. From lakefront walks and neighborhood festivals to rooftop dining and outdoor concerts, the city comes alive when the weather warms up. Whether you're a longtime Chicagoan or visiting for the weekend, there's no shortage of things to do in Chicago this summer.

After spending the day enjoying the city's beaches, street festivals, farmers markets, or exploring neighborhoods like Wicker Park, there's no better way to end the evening than with a live comedy show.

Located in the heart of Wicker Park, The Den Theatre welcomes nationally touring comedians all summer long, making it one of the best destinations for live comedy in Chicago.

Here's who's coming to Chicago this summer.


Sammy Obeid

Stand-up comedian Sammy Obeid is known for his sharp, intelligent humor and impressive background in mathematics.

Obeid gained national recognition after appearing on shows like Last Comic Standing and has since built a strong following through his stand-up tours and online content. His comedy often blends logic, storytelling, and clever observations, making his performances both thought-provoking and highly entertaining.


Gary Gulman's 7th Hour

One of the most respected joke writers in comedy, Gary Gulman has earned praise for his thoughtful storytelling and brilliantly crafted stand-up.

Whether you've seen his HBO special The Great Depresh or are discovering him for the first time, his latest tour offers one of the best opportunities to experience world-class stand-up comedy in Chicago this summer.


Ben Palmer

Australian comedian Ben Palmer has become an international sensation thanks to his lightning-fast crowd work and viral clips shared by millions online.

Every show is different, making Ben Palmer one of the most exciting comedians to experience live.


Martin Amini

Comedian Martin Amini has quickly become one of the most exciting rising voices in stand-up comedy.

Drawing from his multicultural background, Amini delivers a unique comedic perspective that resonates with audiences across the country. In addition to touring internationally, he is the founder of Room 808, a comedy club that has become a major hub for stand-up in Washington, D.C.


Sam Taggart

Comedian Sam Taggart has built a devoted following through his fearless crowd work and energetic stage presence.

If you enjoy interactive stand-up where every audience becomes part of the show, this is one of the can't-miss comedy events of the summer.


James Austin Johnson

Comedian and actor James Austin Johnson has gained national attention as a cast member on Saturday Night Live.

Known for his spot-on impressions and sharp comedic timing, Johnson has quickly become one of the most recognizable rising stars in comedy. His stand-up performances combine impressions, storytelling, and observational humor.


Therapy Gecko Live

Unlike any other live show you'll experience this summer, Therapy Gecko Live combines comedy, audience participation, and heartfelt conversations into one unforgettable evening.

Hosted by internet sensation Lyle Drescher, audiences become part of the experience as the Therapy Gecko offers humorous advice, listens to real-life stories, and creates a show that's completely different every night.




Carly Kazmer