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Maxwell Street Market

7 AM - 3 PM
Maxwell Street Market 800 S. Des Plaines St, Chicago South Loop


Do you enjoy chomping on a fresh churro while sifting through weathered tools, ball caps, and odds and ends? Of course you do.

Fantastic Super Great Nation Numero Uno

Open run: Thu 8 PM, Fri-Sat 8 and 11 PM, Sun 7 PM
Second City E.T.C. Piper's Alley, 1608 N. Wells St., Chicago Old Town

Buy Tickets$19-$46


In the weeks and now days leading up to the inauguration, it seems like the jokes about Trump and the current state of our political climate are basically writing themselves. Between rumors of golden showers and the president-elect's meeting with Steve Harvey, it sometimes feels as if we're all living in one long political sketch. So where are comedians supposed to go from here? Continue reading >> 312-337-3992

The Winner . . . of Our Discontent

Wed-Thu 8 PM, Fri-Sat 8 and 11 PM (except 12/31, 7 and 10 PM), Sun 7 PM (no show 12/25), Tue 8 PM; also Tue 12/20-Thu 12/22 and Tue 12/27-Thu 12/29, 11 PM
Second City 1616 N. Wells St., Chicago Old Town

Buy Tickets$19-$46


The Second City is nothing if not responsive. I mean, really: Nothing. Responsiveness is the whole point of an improv-based, satirical theater. The institution has no entertainment value if its ensemble members fail to respond to one another and no relevance if it fails to respond to the world. Continue reading >> 312-337-3992

Dream Freaks Fall From Space

Open run: Wed-Thu 8 PM, Fri-Sat 8 and 11 PM, Sun 4 PM, Tue 8 PM
Second City 1616 N. Wells St., Chicago Old Town

Buy Tickets$29-$46


Second City is in denial. Donald Trump is our president, and along with that comes a host of issues regarding race, gender equality, LGBTQ rights, and police brutality, among other things. The cast of the brand-new yet already outdated main-stage revue Dream Freaks Fall From Space tackle these loaded topics by mentioning them, then moving right along. And speaking of denial, scenes break one of the most fundamental rules of improvisation—embody the spirit of "yes, and . . . " to complement your partner onstage. Here instead actors deny ideas with "What are you talking about?" Second City is the tentpole of Chicago comedy for the rest of the country, but Dream Freaks feels like it was concocted in an intermediate-level improv class where mere nods get laughs and politics get skewered with Pixy Stix. Continue reading >> 312-337-3992

The Best of Second City

Open run: Sat and Sun 4 PM, Mon 8 PM
Second City 1616 N. Wells St., Chicago Old Town

Buy TicketsPrices vary


The finest sketches, songs, and improvisations from the company's 50-year history, performed by Second City's roster of rising talent. 312-337-3992

Serena Ryder

Mon., July 23, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

The Second City's Improv All-Stars

Open run: Mon 8 PM
Up Comedy Club 230 W. North Ave., Chicago Old Town


The Second City's top performers present their interactive improv every week, directed by Mick Napier. 312-337-3992

Marcus Johnson & Kathy Kosins

Tue., July 24, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Show & Tell

Open run: Tue 8:30 PM
iO Theater, The Mission Theater 1501 N. Kingsbury, Chicago Other North


Second City, iO, Annoyance—Chicago's improv institutions are schools as well as theaters. But so far as I know, nobody has combined the two functions in a single entertainment until now. This series allows improvisers to, as the tagline goes, show you what they do and tell you how they do it. My experience will probably differ from yours. For one thing, the ensemble I saw comprised performers from various teams, so they weren't necessarily used to playing with one another; future installments will feature established teams. And the audience I sat with included lots of improv students, whose questions skewed the conversation toward technicalese; that may change as more civilians take part. What will likely remain the same is a format where players perform scenes, from duets to long-form Harolds, following each with a Q and A. If you're as lucky as I was, you'll see energetic, creative bits and learn something too. —Tony Adler

Corazon de Granada

Wed., July 25, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Comedians You Should Know

Open run: Thu 9 PM


A mix of barflys and independent comedy fans flocks to this weekly showcase, one of the best in the city. The room is friendly, and if hecklers appear, they're shut down affably by Chicago's top stand-ups. It's not a place to try out new material, so the comedians hit jokes hard. And the audience, sitting close and around the stage like a big hug, welcomes the change of pace from the bar's drunk tomfoolery. CYSK is an appropriate name. 312-642-0700

Sonny Landreth, Paul Cebar

Fri., July 27, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

God Street Wine

Sun., July 29, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side


312-733-9463

Ian Maksin & Guitarra Azul

Mon., July 30, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side


312-733-9463

Sawyer Fredericks, Beth Bombara

Wed., Aug. 1, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Frank Orrall

Thu., Aug. 2, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Pat McGee

Fri., Aug. 3, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Lori McKenna

Sat., Aug. 4, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Kevin Whalum

Sun., Aug. 5, 7 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Nikka Costa

Tue., Aug. 7, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Tower of Power

Wed., Aug. 8, 8 p.m., Thu., Aug. 9, 8 p.m. and Fri., Aug. 10, 7 & 10 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Vivian Green

Sat., Aug. 11, 7 & 10 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Over the Rhine

Sun., Aug. 12, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Jean-Luc Ponty

Aug. 13-14, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Talisk & Doolin'

Wed., Aug. 15, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Robben Ford

Thu., Aug. 16, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Ari Hest

Fri., Aug. 17, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Don McLean

Sun., Aug. 19, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463

Shelby Lynne

Mon., Aug. 20, 8 p.m.
City Winery 1200 W. Randolph St., Chicago Near West Side

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312-733-9463