Best Comedy Clubs in Chicago

Where to bust a gut in the funniest city in the world

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Damn right, the funniest—and this spring the merriment scales even greater heights. Consider: As this magazine went to press, Los Angeles’s fabled Laugh Factory was scheduled to open in the newly renovated Lakeshore Theater (its owner, Jamie Masada, promises that big names such as Tim Allen, Dave Chappelle, Carlos Mencia, and Bob Saget will grace the marquee). The Second City’s new standup venue is still just a few months old. The Chicago Improv Festival, with more than 80 acts, arrives at the end of April (click for our guide to the fest). Even the staff of The Onion is bowing to the trend: The satirical newspaper is ditching New York City for Chicago later this year. The downside of this flurry? The sheer volume of comedic choices here can be paralyzing. So our reporter visited scads of comedy shops around town to separate the hilarious from the hideous. A dozen destinations made the cut. Read on for her expert picks.

THE ANNOYANCE THEATRE & BAR
4830 N. Broadway; 773-561-4665, annoyanceproductions.com
What it offers: Improv and sketch
Backstory:: Twenty-four years ago, Mick Napier founded The Annoyance. In 2004, he codified his the-only-rule-is-no-rules philosophy in a book, Improvise, which has become a revered manual for aspiring improvisers. Today, Napier presides over the operation’s handsome digs in Uptown. In addition to providing an artistic home for the legendary comedienne Susan Messing, The Annoyance also welcomes budding writers who want to stage their work for a discerning crowd. (Past hit shows include Skiing Is Believing, Burlesque Is More, and 40 Whacks: A Lizzy Borden Musical.) We also dig the lobby’s high-low assortment of things to do: Play board games while sitting under a chandelier. Sip a Cosmopolitan or a PBR. Both, please, thank you.
Best for: You and your sullen teenager or anyone who ever insinuated that you aren’t “with it”
Must see: In a World. . . , Tuesdays at 9:30 p.m. ($8); Messing with a Friend, Thursdays at 10:30 p.m. ($5)

CHICAGO UNDERGROUND COMEDY
Beat Kitchen, 2100 W. Belmont Ave.; 773-281-4444, chicagoundergroundcomedy.com
What it offers: Standup only
Backstory: “You are NOT going to see hack comedy performances detailing tired premises such as ‘the difference between men and women.’ ” So says the website for Chicago Underground Comedy, the Tuesday night carousel of talent in the backroom of Beat Kitchen, a bar in Roscoe Village (chalkboard beer list, pink Christmas lights, grimy tiles) where working comedians congregate. Instead, you’ll hear well-known local joke tellers dispense fresh alt-comedy about breakups, injuries, misunderstandings, working at Starbucks, and how to get a DUI on a bicycle.
Best for: A young, well-educated broke person
Must see: The fearless Ever Mainard and the always-cantankerous Mike Stanley, Tuesdays at 9:30 p.m. ($5)

THE COMEDY BAR
157 W. Ontario St.; 773-387-8412, comedybarchicago.com
What it offers: Standup only
Backstory: Three nights a week, the River North nightclub Ontourage places 160 chairs on the dance floor and becomes The Comedy Bar. These evenings attract polished standup veterans, usually playing to a mix of tourists and young Loop professionals. In a current show, Sean Flannery interweaves his monologue about near-death experiences—he has suffered 32 broken bones—with drawings, photos, and video clips. The swanky décor, reasonable ticket prices, and no drink minimum are pluses. Feel free to channel your Night at the Roxbury alter ego.
Best for: Someone dipping a toe into the city’s comedy pool
Must see: Flannery’s Never Been to Paris, Thursdays at 8:30 p.m. ($10); Mike Leibovitz, April 20 and 21 at 8 and 10 p.m. ($10)

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