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Jetsetter Guides

72 Hours in Chicago

There's always something going down in Chi-Town. But where to go and what to see when you only have a weekend to experience it all? We weigh in on our top Windy City picks.

See recent posts by Siobhan Reid


Touristy though it may be, you can’t visit Chi-town without a trip down the river. Skip the cheesier cruises and book the tour from the Chicago Architectural Foundation, which tells the tale of the city’s rebuilding after the Great Chicago Fire of 1871. You’ll hear all about the city’s architectural masterpieces, while taking in the Instagram-worthy views. After the trip, linger on the Chicago Riverwalk on the south bank of the river (parts of the walkway, set to be completed in 2016, are open and have killer views of the bridges overhead). It’s worth a quick stroll down nearby Magnificent Mile before lunch at The Purple Pig, where locals linger over small plates like fried artichokes, Olive-oil poached tuna, and Pig’s ear with crispy kale. Work off the meal with a walk through Millennium Park, then hop the Green Line L to the West Loop neighborhood for an evening foodie crawl. Start at The Aviary, chef Grant Achatz inventive cocktail bar for a round that might include a giant ice balloon you have to break open for the booze. Around the corner is the new Momotaro with an exhaustive sushi and Robata menu (leave room for the chili-roe spaghetti) or go old-school at the clubby red sauce Italian favorite Formento’s. Others you’ll want to check out (though not all in one night, of course): Achatz’s newest spot, Next, the Publican, Girl and the Goat, and chef Perry Hendrix’s perennially-packed Avec. End the night on a plush lounger on the rooftop of Soho House Chicago, where fireplaces keep the temperature toasty when it’s chilly outside.


Wake up early (if it doesn’t hurt too much) and rent a bike from Bike Chicago or Divvy to cruise some of the 18 miles of trails edging Lake Michigan. Make your way North to Lincoln Park and lock up at the Green City Market. The organic market has a grazer’s feast of fresh smoothies, wood-fired pizzas and French pastries. Across the street, there’s the Lincoln Park Zoo, one of the nation’s few remaining free zoos. Check out the new hot-spring-soaking eight-member snow monkey troop in the just-opened Regenstein Macaque Forest. Chicago is chest-beating proud of its theater scene and has more than 200 companies. Get tickets to a Tony winner like Steppenwolf or the Goodman or go for one of the smaller edgier groups like The House, which writes much of its own material, or The Hypocrites, known for its goofy adaptations of Gilbert & Sullivan musicals. Take in the sunset at the Cerise, then go for a post-show dinner at the buzzy Fat Rice, where chef Abraham Conlon’s turns out creative takes on Macau cuisine. Order the signature arroz gordo (fat rice). with jasmine rice, prawns, clams, Chinese and Portuguese sausages, marinated chicken, hard-boiled eggs, and sweet and spicy peppers.


You can sleep in and still catch brunch until 3pm at Terzo Piano, the window-wrapped third-floor restaurant atop the Art Institute of Chicago’s Modern Wing. Then browse the museum, hitting up the standout Impressionist and Post-Impressionist collections, as well as the curious miniature rooms that represent various architectural styles. Hit up one of the city’s newest breweries for the afternoon. In hip Logan Square, Revolution Brewing pairs its ales and lagers with a suds-centric menu of bacon fat popcorn and chipotle flank steak. In an industrial corner of Pilsen, the California-based brewer Lagunitas offers free sampling tours and has a laid-back pub featuring live music and delicious pulled pork nachos. Cap off your Chicago weekend with a comedy show at Second City, in Old Town. The company that popularized improv counts alumni from Bill Murray and John Belushi to Tina Fey and Stephen Colbert; it also houses a second stage for smaller productions and the stand-up comedy club, Up, all guaranteed to get you near tears with laughter.



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