“After college, I knew I wanted to work in comedy, so the first thing I did was go to where the comedy was. I moved from Charlottesville to Chicago, because that’s where The Second City and Improv Olympics are.” — Tina Fey

Chicago is a destination with a sense of humor. With plenty of venues dedicated to stand-up, sketch, and improv comedy, the Windy City is rightfully known as one of the funniest cities in the world. In that light, here’s what you should know if you’d like to laugh your way through the Midwestern metropolis.

The Second City

Probably the best-known of Chicago’s comedy clubs, the Second City has a long history of tickling its audience’s funny bones. The original club opened in December 1959, and its members have redefined improv and sketch comedy over the past six decades. Just about everyone knows the names of its most famous alumni: Tina Fey, Amy Poehler, Steve Carell, Stephen Colbert, and Bill Murray, among other.

Most Second City shows comprise original sketches, songs, and improv scenes performed by the featured cast, although you can also find stand-up performances or student productions at the company’s sister theaters. Mainstage tickets are fairly expensive, but with no drink minimum, you won’t have to pay for an add-on once you arrive at the show.

The Second City’s main theater is located at 1616 N. Wells Street. The company’s e.t.c. theater is next door, at 1608 N. Wells Street, and its UP Comedy Club is around the corner at 230 W. North Avenue.

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iO Theater (formerly Improv Olympics)

This theater specializes in improv comedy, with its signature long-form style known as “the Harold.” Each Harold follows a loose structure that lets the actors tie a few unrelated scenes together, running anywhere between 25 and 40 minutes in length. And every Thursday and Friday, the popular Improvised Shakespeare Company performs at the theater — so if you’d like to see talented actors speaking in Old English and devising characters, plot twists, and musical numbers on the spot, you know where to go!

The iO Theater is located at 1501 N. Kingsbury Street.

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The Annoyance Theatre and Bar

The Annoyance Theatre is (proudly) edgier than the other comedy bars in the Windy City — think buckets of fake blood, actors stripping down to their underwear, and wacky premises for improv shows.

The theater’s first big hit was its original musical, “Coed Prison Sluts,” which ran for 11 straight years, and then came back to the stage in the late 2000s. Although the musical isn’t currently being performed, you don’t need to fret — the theater has replaced it with plenty of other bawdy shows.

Another thing to note is that Annoyance tickets never cost more than $20, with the cheapest tickets available for weekday and B-stage shows. So, if you don’t want to break the bank during your night on the town, you’re in luck!

The Annoyance Theater is located at 851 W. Belmont Avenue.

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Zanies Comedy Club

If you’re a big fan of stand-up, this just might be the club for you. Celebrating its 40th anniversary this year, Zanies was Chicago’s first establishment dedicated to stand-up, making it a mainstay on the city’s comedy scene. It features touring headline acts every night of the week, so no matter when you’re in town, you should be able to squeeze a show into your travel plans.

Note that this club has a two-drink minimum policy, so minors are not allowed inside.

Zanies Comedy Club is located at 1548 N. Wells Street.

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The Comedy Bar

This club has a lot going for it: no drink minimum; no age requirements; pizzas, snacks, and drinks for purchase; and tons of stand-up comedians. Open-mic nights are free, but with relatively inexpensive tickets available for other shows, you might want to consider going to a headlining act — either on the main or B stage. The shows run every night of the week, attracting some of the funniest talent in the city.

The Comedy Bar is located at 500 N. LaSalle Street.

Chicago Underground Comedy

Even if you’re on a budget or visiting the Windy City in the middle of the week, you can still enjoy a funny night out, thanks to Chicago Underground Comedy. The club describes itself as bringing “alt-comedy” performers to center stage, and the shows (which feature everything from stand-up to sketches) take place every Tuesday at 9:30 p.m. Tickets only cost five dollars. Yep — you read that correctly.

Chicago Underground Comedy is located in a venue called the Beat Kitchen, at 2100 W. Belmont Avenue.

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Chicago is a city that will keep you laughing — and even though we’ve named several of its best comedy clubs, we’ve barely scratched the surface. So, the next time you’re in the Windy City, pick your theater, buy a ticket, and get ready to laugh until your abs are sore.

Cover photo by Shay Bengtson