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Comedy Shows in Chicago – May-June 2023

“A man in China accidentally unearthed a 700-year-old figurine after he pulled over to the side of the road to relieve himself, and discovered he was urinating on the object. It’s a story the man loves to tell most… when people are holding the figurine.”  – Colin Jost

Jost is moving out from behind the desk at SNL’s Weekend Update to grab the mic at The Chicago Theatre on June 25th.  And, he’s just one on a long list of comics hitting the Chicago stages in May and June of 2023.

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Chicago Comedy Shows May-June Highlight Reel

Stand Out Stand Ups

Chicago Comedy Clubs

May-June Comedy Shows in Chicago – the Highlight Reel

Note: These are taken from the official Chicago Events Calendar by Evvnt hosted here on OTL City Guides.

A Round of Applause for Chicago Seat Fillers

If you live in the Windy City and love comedy (plus other live shows!), be sure to check out OTL Seat Fillers. Seat Fillers have been in Chicago for eight years, attending theatre, comedy, and special events. Low membership dues cover 2 or 4 tickets per show – and you never pay for tickets or any additional (and crazy!) charges!

Stand up comedy, stand up comedians

A Few Stand Out Stand Ups in Chicago in May & June

Drunk – Drunk Shakespeare (and Drunk Debates)

During the Drunk Shakespeare Society meetings, five professional actors get together. After drinking five shots, one of them takes on a major role in a Shakespearean play. The four sober actors try to keep a straight face while the script deviates from its intended course. There is always a different show depending on who is drinking… and what they’re drinking!

The “meetings” are held at the Lounge at the Lion on 182 N Wabash, behind the Chicago Theatre. It’s the same locale for Drunk Debates. You don’t need to be drunk to enjoy the shows, but a craft cocktail won’t hurt!

A Free Ticket Opportunity at The Laugh Factory

The Laugh Factory is one of Chicago’s premier comedy clubs with other locations including Las Vegas, Reno, and Long Beach. While you typically have to pull out your wallet for ticket reservations, plan for the 9 pm show on Tuesdays, and you’re on the comp list (and so is everyone else!).

Just don’t forget the two-drink minimum – and tip your waiters.

An SNL Pattern is Emerging

Season 48 is a wrap, and reruns are on the schedule. So, the cast of Saturday Night Live is dispersing and, apparently, heading to Chicago.

Colin Jost is coming to The Chicago Theatre. Chris Redd has a few dates at The Den Theatre. You can catch Michael Longfellow at Zanies, and alums Tina Fey and Amy Poehler at The Chicago Theatre. Visit the Chicago Events Calendar for dates, times, and ticket info.

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OTL Seat Fillers, seat filling, how to be a seat filler

Looking for a Particular Comedy Club in Chicago?

We’re covering laughs from all angles, including a dedicated Chicago Comedy Clubs page. So, be sure to bookmark OTL City Guides.

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