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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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Market PicksHotels Selected for Top Ratings and Value + 5% Groupon Bucks Credit

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Hyatt Regency Chicago
Hyatt Regency Chicago
Chicago, Illinois

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With a stay at Hyatt Regency Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue Bridge and minutes from Bridgehouse and Chicago River Museum. This 4-star hotel is close to Art Institute of Chicago and Hancock Tower.

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Park Hyatt Chicago
Park Hyatt Chicago
Chicago, Illinois

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With a stay at Park Hyatt - Chicago, you'll be centrally located in Chicago, steps from Chicago Water Tower and Loyola University Museum of Art. This 5-star hotel is close to Millennium Park and Art Institute of Chicago.

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Palomer Hotel
Palomer Hotel
Chicago, Illinois

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With a stay at Palomar Chicago, a Kimpton Hotel in Chicago (Magnificent Mile - River North), you'll be minutes from American Medical Association Headquarters and Wrigley Building. This 4-star hotel is close to Millennium Park and Art Institute of Chicago.

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The Wit Hotel Chicago
The Wit Hotel Chicago
Chicago, Illinois

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With a stay at theWit Chicago - a DoubleTree by Hilton Hotel, you'll be centrally located in Chicago, steps from Chicago Theater and Vietnam Veterans Memorial. This 4-star hotel is close to Art Institute of Chicago and Skydeck Ledge.

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Ivy Boutique Hotel
Ivy Boutique Hotel
Chicago, Illinois

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With a stay at Ivy Hotel, you'll be centrally located in Chicago, steps from Arts Club of Chicago and Northwestern Memorial Hospital. This 4.5-star hotel is close to Millennium Park and Art Institute of Chicago.

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Chicago South Loop Hotel
Chicago South Loop Hotel
Chicago, Illinois

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With a stay at Chicago South Loop Hotel in Chicago (Near South Side), you'll be close to McCormick Place and University of Illinois Chicago. This family-friendly hotel is close to University of Illinois Chicago and Skydeck Ledge.

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Wyndham Grand Chicago Riverfront
Wyndham Grand Chicago Riverfront
Chicago, Illinois

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With a stay at Hotel 71, Wyndham Affiliate, you'll be centrally located in Chicago, steps from Vietnam Veterans Memorial and Bridgehouse and Chicago River Museum. This romantic hotel is close to Art Institute of Chicago and Skydeck Ledge.

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dana hotel and spa
dana hotel and spa
Chicago, Illinois

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With a stay at dana hotel and spa, you'll be centrally located in Chicago, steps from Driehaus Museum and Holy Name Cathedral. This 4-star hotel is close to Millennium Park and Art Institute of Chicago.

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4-Star Mystery Hotel
4-Star Mystery Hotel
Chicago, Illinois

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With a stay at The Blackstone Renaissance Chicago Hotel in Chicago (The Loop - Downtown), you'll be minutes from Museum of Contemporary Photography and Grant Park. This 4-star hotel is close to Millennium Park and Skydeck Ledge.

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Marriott Chicago / Midway
Marriott Chicago / Midway
Chicago, Illinois

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With a stay at Chicago Marriott Midway in Chicago, you'll be near the airport and close to Marquette Park. This hotel is within the vicinity of Morton College and Hawthorne Works Museum.

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Hard Rock Hotel Chicago
Hard Rock Hotel Chicago
Chicago, Illinois

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Renaissance Chicago Downtown Hotel
Renaissance Chicago Downtown Hotel
Chicago, Illinois

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Kinzie Hotel
Kinzie Hotel
Chicago, Illinois

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With a stay at Amalfi Hotel Chicago, you'll be centrally located in Chicago, steps from House of Blues Chicago and minutes from American Medical Association Headquarters. This family-friendly hotel is close to Hancock Tower and Art Institute of Chicago.

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Ramada Inn Lake Shore
Ramada Inn Lake Shore
Chicago, Illinois

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With a stay at Ramada Lake Shore in Chicago (Kenwood), you'll be convenient to Chicago Museum of Science and Industry and University of Chicago. This hotel is within close proximity of Robie House and Oriental Institute Museum.

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British Swim School
British Swim School
Chicago, Illinois

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Swissotel - Chicago is in the heart of Chicago, walking distance from Aon Center and Michigan Avenue Bridge. This 4-star hotel is close to Art Institute of Chicago and Hancock Tower.

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Embassy Suites Chicago - Downtown/Lakefront
Embassy Suites Chicago - Downtown/Lakefront
Chicago, Illinois

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New Year’s Eve Soiree
New Year’s Eve Soiree
Chicago, Illinois

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With a stay at Hilton Chicago- Michigan Ave Cultural Mile, you'll be centrally located in Chicago, steps from Museum of Contemporary Photography and Columbia College Chicago. This 4-star hotel is close to Millennium Park and Willis Tower.

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Club Quarters Chicago
Club Quarters Chicago
Chicago, Illinois

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With a stay at Club Quarters, Wacker at Michigan, you'll be centrally located in Chicago, steps from Bridgehouse and Chicago River Museum and Vietnam Veterans Memorial. This hotel is close to Art Institute of Chicago and Hancock Tower.

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Hotel Lincoln
Hotel Lincoln
Chicago, Illinois

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Hotel Lincoln is in the heart of Chicago, walking distance from Second City and Chicago History Museum. This 4-star hotel is close to Millennium Park and Art Institute of Chicago.

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Waldorf Astoria Chicago
Waldorf Astoria Chicago
Chicago, Illinois

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With a stay at Waldorf Astoria Chicago, you'll be centrally located in Chicago, minutes from Newberry Library and Hancock Tower. This 5-star hotel is close to Millennium Park and Art Institute of Chicago.

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Raffaello Hotel
Raffaello Hotel
Chicago, Illinois

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Courtyard Chicago Downtown/River North
Courtyard Chicago Downtown/River North
Chicago, Illinois

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Hotel Burnham, a Kimpton Hotel
Hotel Burnham, a Kimpton Hotel
Chicago, Illinois

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Renaissance Chicago O'Hare Suites Hotel
Renaissance Chicago O'Hare Suites Hotel
Chicago, Illinois

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When you stay at Renaissance Chicago O'Hare Suites Hotel in Chicago, you'll be near the airport and convenient to Donald E. Stephens Convention Center and Rosemont Theatre. This hotel is within close proximity of Rivers Casino and Allstate Arena.

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Hotel Indigo Chicago Downtown Gold Coast
Hotel Indigo Chicago Downtown Gold Coast
Chicago, Illinois

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Chicago Marriott Dtwn Magnificent Mile
Chicago Marriott Dtwn Magnificent Mile
Chicago, Illinois

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Chicago Marriott at Medical District/UIC
Chicago Marriott at Medical District/UIC
Chicago, Illinois

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Balance Spa and Fitness at the Palmer House Hilton
Balance Spa and Fitness at the Palmer House Hilton
Chicago, Illinois

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Allegro Hotel Chicago
Allegro Hotel Chicago
Chicago, Illinois

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Hotel Monaco Chicago, a Kimpton Hotel
Hotel Monaco Chicago, a Kimpton Hotel
Chicago, Illinois

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