One of the most visited cities in the entire US and often ranked as one of the best places in North America to live, Chicago is the perfect place for people who like to get and about and see the best of what the world has to offer. Renowned for its landmarks, museums, and distinctive culture, Chicago is one of the best spots in all of America for live shows, concerts, comedy, and more.

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Improvisational comedy has always been a big part of Chicago's culture; the first generation of American improv comics set up the famous Compass Players in Chicago during the 1950s, and The Second City took over in 1959 as the first ever continuous improv troupe in the city. A lot of the rules and styles of modern improv comedy were established in Chicago, and countless popular Saturday Night Live comics underwent training at The Second City like Mike Myers, Tina Fey, Stephen Colbert, Steve Carrell, and Dan Aykroyd. Things to do in Chicago

Legendary, world-famous comedians like Robin Williams and John Belushi were also born and grew up in the city itself. It’s easy to see that Chicago is a real home of comedy and there are plenty of hilarious comedy shows to enjoy all around the city.

Best Comedy Shows in Chicago

With such a rich comedic history to the city, it’s actually not uncommon to see comedy shows in random bars, pubs, and music clubs all around the city. Almost anywhere you go in Chicago, you can expect to stumble onto some comedy, but if you’re specifically looking for the best comedy shows and biggest laughs of the Windy City, these are the locations to visit.

1. The Second City - 1616 N Wells St, Chicago, IL 60614, Phone: 312-337-3992

A location that needs almost no introduction, The Second City is essentially the home of improv comedy. This is the location where many legendary American comics first made a name for themselves. Many of the stars we've seen and loved on shows like Saturday Night Live were discovered here, with the Second City's alumni including huge names like Tina Fey, Steve Carrell, Stephen Colbert, Chris Farley, Bill Murray, and more.

Providing some of the best laughs in America for more than five decades, The Second City is one of the most storied and fascinating locations in the world of comedy and a must-visit Chicago spot for anyone with even a passing interest in the art of improv.

2. iO Theater - 1501 N Kingsbury St, Chicago, IL 60642,Phone: 312-929-2401

For all your improv comedy needs outside of The Second City, the iO Theater is the next best thing. This is another of Chicago's most prestigious and esteemed comedy locations, having been established back in 1981 by Del Close and Charna Halpern, both iconic figures in the improv comedy scene.

The likes of Amy Poehler, Chris Farley, Mike Myers, Bill Hader, Seth Meyers, and Stephen Colbert spent time in this theater to hone their craft and the iO still boasts some of the best improv comedy classes and shows anywhere in North America. Just stepping foot in the hallowed halls of the iO Theater is enough to feel something special, and some of the comedy shows held in the theater’s four performance spaces will have your sides splitting with laughter.

3. UP Comedy Club - 230 W North Ave, Chicago, IL 60614, Phone: 312-662-4562

For all kinds of comedy shows in Chicago, the UP Comedy Club offers a lighthearted atmosphere and great food to go along with it. Sketch, improv, and stand up comedy shows can all be enjoyed at this location for very reasonable prices and lots of local and national talents appear on the UP Comedy Club stage each and every week. With various special events held throughout the year and a vibrant schedule of comedy shows, the UP Comedy Club is a great place to spend a fun-filled evening with friends and loved ones.

4. Laugh Factory - 3175 North Broadway, Chicago, IL 60657, Phone: 773-327-3175

The legendary Laugh Factory is one of America's oldest and most successful comedy club chains and the Chicago location has always been a big hit with locals and visitors to the city. Top class comics like Dave Chappelle, Whitney Cummings, Tim Allen, and more have all appeared at this venue and all of the hottest new talents are guaranteed to do some shows here too. At the Laugh Factory, you're sure of two things: big laughs and great memories.