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Chicago Guide

For a quick intro to what makes Chicago great, it’s hard to beat a ride down Lake Shore Drive, the 19-mile stretch of road running along the city’s eastern edge. On one side, you’ve got sparkling Lake Michigan, and, on the other, a string of show-stopping skyscrapers and the city’s “front yard,” Grant Park, home to the Lollapalooza festival and Buckingham Fountain.

What to Know Before You Go

  • Best time to visit: between Memorial Day and Labor Day. The weather can be sticky and the lakefront overcrowded, but summer is Chicago’s time to shine. Knowing the warm temperatures won’t last long, locals take every opportunity to be out and about. There are street parties and music festivals nearly every weekend.
  • City of neighborhoods: Chicago encompasses a large and diverse collection of neighborhoods, each with its own personality. Try a gyro in Greektown, walk through the National Museum of Mexican Art in Pilsen, or catch a Cubs game at Wrigley Field in Lakeview.
  • Forget the car: Traffic in the city can be unrelenting, and parking is expensive. Consider relying instead on the L, Chicago’s elevated train, or taxis—especially if you’re only in town a short while.

Chicago for Foodies

It’s not all about hot dogs and deep-dish pizza anymore. In recent years, the Windy City has garnered lots of attention for its cutting-edge culinary scene. Food & Wine magazine named it one of the 10 Best Restaurant Cities in the world in 2008. The West Loop neighborhood, in particular, has become a popular landing spot for celebrity chefs.

  • The Aviary: Bartenders inject bourbon, sugar, and bitters inside hollow balls of ice at this ambitious cocktail joint. It was recently named the country’s most Outstanding Bar Program by the James Beard Foundation.
  • Girl & the Goat: Top Chef winner Stephanie Izard creates inventive dishes from unconventional cuts of meat, including oven-roasted pig face and duck tongue. Plan ahead, though—reservations fill up months in advance.
  • Au Cheval serves up the best burger in the country, according to Bon Appetit. It’s right across the street from Girl & the Goat.
  • Where to stay: The Crowne Plaza Chicago Metro hotel is conveniently located near all of the above restaurants, as well as Greektown.

Chicago for Arts Lovers

  • Museum Campus: a 57-acre complex along the lake that’s home to three of the city’s best educational institutions. You can watch shark feedings in a 90,000-gallon tank at Shedd Aquarium, go star-gazing at Adler Planetarium, or head to the Field Museum to see the largest and most complete Tyrannosaurus rex fossil ever unearthed
  • Steppenwolf Theatre Company in Lincoln Park is the gold standard for Chicago-style theater—gritty, gutsy plays produced by a fearless ensemble. Several of the troupe’s productions have transferred to Broadway, including a Tony-winning staging of Who’s Afraid of Virginia Woolf?
  • The Second City: This 50-year-old sketch-comedy theater in Old Town launched the careers of Tina Fey, Amy Poehler, Stephen Colbert, John Belushi, and a host of other funny people.
  • The Art Institute of Chicago has an embarrassment of riches, including Grant Wood's American Gothic, Edward Hopper’s Nighthawks and a slew of Impressionist masterpieces.
  • Where to stay: Swissotel, a sleek hotel in the Loop, is just a short walk from the Art Institute and the beloved architectural boat tours along the Chicago River.

Chicago for Shoppers

  • The Magnificent Mile: This famous retail corridor along North Michigan Avenue is a window-shopper’s paradise, with outposts from fashion icons such as Burberry, Chanel, Tiffany, and Neiman Marcus.
  • River North features dozens of art galleries, many of them housed in converted warehouses. This is the best place to check out work by emerging artists.
  • Randolph Street Market: Shop for antiques and vintage furnishings at this European-style indoor-outdoor market.
  • Where to stay: Between purchases, you can partake in afternoon tea at the Drake Hotel—a tradition that was once enjoyed by Princess Diana and Queen Elizabeth II—or follow in the footsteps of Brad and Angelina, who prefer the extravagance of The Peninsula hotel on East Superior Street.
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