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Amy Schumer, Cultish Gyros, and Classic Drive-In Theater: What to Do in Chicago This Week

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Here are the five coolest things to do in and around Chicago this week. We publish a new list every Wednesday, covering Thursday through Wednesday. Stay tuned for insider updates on restaurant openings, festivals, exhibitions, shows, weekend escapes, and more.

August 27 | Performance
To the uninitiated, the idea of partying in a Chicago alley seems…well, dank. But the huge success of last year’s art installation–meets-performance-art-meets-soiree suggests there’s a lot more going on in Loop alleys than dumpsters. This time around, Activate goes steampunk (think pinstripes, pocket watches, 2009’s Sherlock Holmes), with fire installations, aerial acrobatics, and tarot cards. Local visual artists display their work, and a DJ keeps the partygoers moving until the 10 p.m. rooftop after-party and steampunk fashion show at theWit Hotel. 

5–10 p.m. | Haddock Place Alley, bounded by Lake St., State St., Wabash Ave., and Wacker Pl., Chicago | Free | website

August 29 | Comedy
Oddball Comedy Curiosity Festival
The Oddball Comedy and Curiosity Festival, presented by Funny or Die, lands in the Chicago area for a night of stellar stand-up in a venue that’s the polar opposite of a dark, cramped comedy club: the enormous, open-air Hollywood Casino Amphitheatre (AKA First Midwest Bank Amphitheatre) in Tinley Park. Besides Schumer and Ansari, the Chicago lineup includes Nick Kroll (Comedy Central’s Kroll Show), Jay Pharaoh (SNL), Bridget Everett (the unforgettable cabaret singer on Inside Amy Schumer), and Chicago’s own T.J. Miller (Silicon Valley). 

5 p.m. | Hollywood Casino Amphitheatre, 19100 Ridgeland Ave., Tinley Park | (708) 614-1616 | From $42 | website

August 29–30 | Food festival
Chicago Food + Wine Festival
Think of this new culinary extravaganza as the best buffet the city has ever seen. Graze on bites and booze from 90 food, beer, and spirits vendors and, best of all, taste top dishes from such Chicago chef heroes as Vie’s Paul Virant, Hoosier Mama Pie Company’s Paula Haney, and Black Dog Gelato’s Jessica Oloroso. Still hungry? Evening events include Toast and Taste, a sampling of culinary creations from the likes of Rick Bayless (Frontera Grill, Topolobampo, Xoco), Vinny Dotolo and John Shook (L.A.’s Animal), and Jonathan Waxman (NYC’s Barbuto). 

11 a.m.–4 p.m. | Lincoln Park’s Grove 2 and 3, between LaSalle Dr. and the South Pond, Chicago | From $175 | website

Restaurant opening
The Halal Guys
How could a simple dish of chicken or gyros over rice inspire New Yorkers to wait in line for hours in front of the Halal Guys street meat cart? Chicagoans can finally find out: The Halal Guys storefront opened last week in the Gold Coast. It’s the first outside-NYC expansion in Halal Guys’ plans for world domination—200 more locations worldwide are in the queue, including four more in Chicago. What’s the secret to its success? Many say it’s the mysterious “white sauce” that gets slathered on everything. The recipe is a closely guarded secret, though fans are so crazy for it they’ve tried to reverse engineer it. 

Monday–Thursday & Sunday 11 a.m.–11 p.m.; Friday & Saturday 11 a.m.–4 a.m. | 49 W. Division St., Chicago | (312) 877-5575 | website

Weekend Escape | Road trip
Cascade Drive In
What better way to close out summer than a short drive to West Chicago’s Cascade Drive In? The last drive-in movie theater in the Chicago area, Cascade recently updated for the 21st century with digital projection, stereo sound (via the radio in your car or complimentary speakers), a picnic area where you can grill your own food, and an outdoor heated patio to keep you warm when the temperatures dip at night.

100 E. North Ave., West Chicago | (630) 231-3151 | $10 | website

Laura Baginski is a Chicago-based writer and editor who specializes in travel and parenting. Because of the latter, the former doesn’t happen as much as she’d like.

Planning a trip? Check out the AFAR guide to Chicago.

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