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Chicago September 22–28: Oktoberfest Chicago & Fall Dinner Crawl

The best of what to do in and around Chicago this week

Welcome fall with food in Chicago this week, but first take in a play from Mexico City at the Shakespeare Theater. Then it’s Oktoberfest time, so get your liver ready. Or head instead to Chicago Gourmet, which brings great food and top chefs to one place. Top it off with a fun dinner crawl, where you’ll get to try even more local restaurants.

AFAR Local is our weekly insider guide to the best of what’s happening in cities around the U.S. 

September 22–24 | Theater
Enamorarse de un Incendio
Foro Shakespeare, a world-renowned social justice theater company from Mexico City, has joined Shakespeare 400 Chicago and well-known Chilean playwright Eduardo Pavez Goye to bring audiences Enamorarse de un Incendio. The play, which tells the stories of three relationships in interlacing vignettes, focuses on the theme of unrequited love. The play will be performed in Spanish, with an English translation projected on the staging area before each scene.
7:30 p.m. | Chicago Shakespeare Theater, 800 E. Grand Ave., Chicago | $38 | website

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September 23–25 | Drink
Oktoberfest Chicago
Now in its 16th year, Oktoberfest Chicago is the Midwestern version of Germany’s famous fall celebration. There will be music and handmade bratwursts to enjoy, and, of course, the party wouldn’t be complete without craft beer tastings on both evenings. You’ll be temporarily transported to Germany, complete with German bands and local Chicago cover bands (local favorite 16 Candles will perform on Saturday night). This year’s event is set to be even bigger, louder, and better than ever before.
Times vary | St. Alphonsus Church, 1429 W. Wellington Ave., Chicago | $5 | website 

September 23–25 | Food festival
Chicago Gourmet
This food festival celebrates all of Chicago’s amazing food and the chefs that dish it out. There will be live cooking demonstrations, where chefs will share their techniques and tell their stories, as well as interactive drink seminars. Plus, Millennium Park will be filled with restaurants, wineries, breweries, and spirit purveyors giving tastings. The lineup includes chefs such as Todd English, Stephanie Izard, Art Smith, and Jose Garces. And make sure you save room for the highly anticipated burger showdown at the Harris Theater rooftop on Friday night.
Times vary | Millennium Park, 201 E. Randolph St., Chicago | $295 | website

Oktoberfest Chicago

September 23–25 | Escape the city
Des Moines, Iowa
The best time of year to get to the capital of Iowa is now, when Oktoberfest is taking place (September 23–24). You’ll be able to take polka-dancing lessons, enter a stein holding contest, and drink every type of German beer imaginable under festive tents in downtown Des Moines this weekend. The Des Moines Art Center is also a worthy place to visit, housing modern and classic works. Or take a tour of the historic estate Salisbury House & Gardens, and you’ll for sure return with some serious house envy.

September 27 | Food
Wicker Park Bucktown Fall Dinner Crawl
Snackers, rejoice. Grab a map and head over to the boutique-filled neighborhoods of Wicker Park and Bucktown, and you’ll be able to sample food from about a dozen restaurants. This is a choose-your-own-adventure kind of party, and there are three different paths to take: the Fork Route (restaurants include Big & Little’s, Xoco Bistro, Antique Taco), the Knife Route (restaurants include Urbanbelly, Goddess & Grocer, and Coast Sushi Bar), or the Spoon Route (restaurants include Smoke Daddy, 5411 Empanadas, and Harvest Moon).
6–9 p.m. | Locations vary | $30 | website

Danielle Braff lives in Chicago with her husband, two daughters, two cats, and her dog. When she’s not writing, she’s out photographing her city and running around frantically trying to fit as many events as she can into her day. You can check out her other articles at Daniellebraff.com.

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