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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

Get a 5% Groupon Bucks credit when you book a Market Pick hotel here.
theWit Chicago - A DoubleTree by Hilton Hotel
Chicago, Illinois

5%

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.

5% Groupon Bucks Credit

Ivy Boutique Hotel
Chicago, Illinois

5%

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.

5% Groupon Bucks Credit

The Chicago South Loop Hotel
Chicago, Illinois

5%

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.

5% Groupon Bucks Credit

Wyndham Grand Chicago Riverfront
Chicago, Illinois

5%

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.

5% Groupon Bucks Credit

Dana Hotel & Spa
Chicago, Illinois

5%

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.

5% Groupon Bucks Credit

Marriott Chicago / Midway
Chicago, Illinois

5%

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.

5% Groupon Bucks Credit

Amalfi Hotel Chicago
Chicago, Illinois

5%

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.

5% Groupon Bucks Credit

The Wheeler Mansion
Chicago, Illinois

5%

The Wheeler Mansion has narrowly escaped destruction not once, but twice. One of the few remaining mansions to survive the Great Chicago Fire of 1871, the residence changed hands several times until the late 1990s, when it was slated to be turned into a parking lot. Thanks to a last-minute bid from a local contractor, the French-style home underwent a meticulous restoration (which won the Preservation Excellence Award from the city), and now serves the neighborhood as a stately boutique hotel. A short walk from the parks along Lake Michigan and the Museum Campus, the hotel is now a fixture in the city's South Loop.

5% Groupon Bucks Credit

Waldorf Astoria Chicago
Chicago, Illinois

5%

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.

5% Groupon Bucks Credit

Doubletree Chicago Magnificent Mile
Chicago, Illinois

5%

A stay at DoubleTree by Hilton Chicago - Magnificent Mile places you in the heart of Chicago, walking distance from Arts Club of Chicago and Northwestern Memorial Hospital. This family-friendly hotel is close to Millennium Park and Art Institute of Chicago.

5% Groupon Bucks Credit

Chicago Marriott Dtwn Magnificent Mile
Chicago, Illinois

5%

With a stay at Chicago Marriott Downtown Magnificent Mile, you'll be centrally located in Chicago, steps from Tribune Tower and minutes from Arts Club of Chicago. This hotel is close to Millennium Park and Art Institute of Chicago.

5% Groupon Bucks Credit

Trump International Hotel & Tower
Chicago, Illinois

5%

With a stay at Trump International Hotel & Tower Chicago in Chicago (Magnificent Mile - River North), you'll be minutes from Wrigley Building and Tribune Tower. This 5-star hotel is close to Hancock Tower and Art Institute of Chicago.

5% Groupon Bucks Credit

Embassy Suites Chicago Downtown
Chicago, Illinois

5%

With a stay at Embassy Suites Chicago Downtown, you'll be centrally located in Chicago, steps from American Medical Association Headquarters and minutes from Driehaus Museum. This family-friendly hotel is close to Millennium Park and Art Institute of Chicago.

5% Groupon Bucks Credit

Courtyard Midway
Chicago, Illinois

5%

With a stay at Courtyard Chicago Midway Airport in Chicago (Bedford Park), you'll be close to Marquette Park. This hotel is within the vicinity of Morton College and Hawthorne Works Museum.

5% Groupon Bucks Credit

Chicago Marriott O'Hare
Chicago, Illinois

5%

When you stay at Chicago Marriott O'Hare 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.

5% Groupon Bucks Credit

Holiday Inn Chicago-Mart Plaza
Chicago, Illinois

5%

With a stay at Holiday Inn Chicago-Mart Plaza in Chicago (Magnificent Mile - River North), you'll be minutes from Merchandise Mart and close to Skydeck Ledge. This family-friendly hotel is close to Willis Tower and Millennium Park.

5% Groupon Bucks Credit

Holiday Inn
Chicago, Illinois

5%

When you stay at Holiday Inn O'Hare 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.

5% Groupon Bucks Credit

The W Hotel Chicago City Center
Chicago, Illinois

5%

A stay at W Chicago City Center places you in the heart of Chicago, steps from Chicago Board of Trade Building and Skydeck Ledge. This 4-star hotel is close to Willis Tower and Art Institute of Chicago.

5% Groupon Bucks Credit

Residence Inn Chicago Midway Airport
Chicago, Illinois

5%

Property Location With a stay at Residence Inn Marriott Chicago Midway in Chicago (Bedford Park), you'll be close to Marquette Park. This hotel is within the vicinity of Childrens Museum of Oak Lawn and Morton College.

5% Groupon Bucks Credit

Central Loop Hotel
Chicago, Illinois

5%

With a stay at Central Loop Hotel in Chicago (The Loop - Downtown), you'll be minutes from Chicago Board of Trade Building and Skydeck Ledge. This hotel is close to Willis Tower and Art Institute of Chicago.

5% Groupon Bucks Credit

Hyatt Resorts
Chicago, Illinois

5%

With a stay at Hyatt Chicago Magnificent Mile, you'll be centrally located in Chicago, steps from Arts Club of Chicago and Northwestern Memorial Hospital. This 4-star hotel is close to Millennium Park and Art Institute of Chicago.

5% Groupon Bucks Credit

Courtyard by Marriott Mag Mile
Chicago, Illinois

5%

With a stay at Courtyard by Marriott Chicago Magnificent Mile, you'll be centrally located in Chicago, steps from Arts Club of Chicago and Northwestern Memorial Hospital. This family-friendly hotel is close to Millennium Park and Art Institute of Chicago.

5% Groupon Bucks Credit

Crowne Plaza
Chicago, Illinois

5%

With a stay at Silversmith Hotel & Suites, you'll be centrally located in Chicago, steps from Haskell Building and Bank of America Theatre. This family-friendly hotel is close to Art Institute of Chicago and Skydeck Ledge.

5% Groupon Bucks Credit

The Westin Chicago River North
Chicago, Illinois

5%

With a stay at The Westin Chicago River North, you'll be centrally located in Chicago, steps from House of Blues Chicago and minutes from Vietnam Veterans Memorial. This 4-star hotel is close to Art Institute of Chicago and Skydeck Ledge.

5% Groupon Bucks Credit

JW Marriott Chicago
Chicago, Illinois

5%

A stay at JW Marriott Chicago places you in the heart of Chicago, steps from Chicago Board of Trade Building and Skydeck Ledge. This 4-star hotel is close to Willis Tower and Art Institute of Chicago.

5% Groupon Bucks Credit

Thompson Chicago
Chicago, Illinois

5%

With a stay at The Sutton Place Hotel by the Magnificent Mile, you'll be centrally located in Chicago, minutes from Newberry Library and Hancock Tower. This romantic hotel is close to Millennium Park and Art Institute of Chicago.

5% Groupon Bucks Credit

Radisson Blu Aqua
Chicago, Illinois

5%

Radisson Blu Aqua Hotel Chicago is in the heart of Chicago, walking distance from Aon Center and Harris Theater. This 4-star hotel is close to Art Institute of Chicago and Hancock Tower.

5% Groupon Bucks Credit

InterContinental Chicago
Chicago, Illinois

5%

With a stay at InterContinental Chicago Magnificent Mile, you'll be centrally located in Chicago, steps from Tribune Tower and Wrigley Building. This 4.5-star hotel is close to Millennium Park and Art Institute of Chicago.

5% Groupon Bucks Credit

The Whitehall Hotel
Chicago, Illinois

5%

A stay at The Whitehall Hotel places you in the heart of Chicago, steps from 900 North Michigan Shops and Hancock Tower. This romantic hotel is close to Millennium Park and Art Institute of Chicago.

5% Groupon Bucks Credit

ACME Hotel Company Chicago
Chicago, Illinois

5%

Please note ACME Hotel Company is 100 PCT non smoking. 130 guest rooms on 15 floors including 130 double rooms, 33 twin rooms, 25 suites and meeting/conference facilities. Amenities include AC2 SUITE DBL/COMP WIFI/ACCESIBLE/CTY VIEWS WD FLRS/FRDGE/MICROWAVE/MINIBAR/404 SQFT SU1 SUITE KNG/COMP WIFI/LIVNG RM/CTY VIEWS WD FLRS/FRDGE/MICROWAVE/MINIBAR/404 SQFT C2Q STD DBL/COMP WIFI/46 LED TV/HRD WD FLRS FRDGE/MICROWAVE/LRG DESK/MINIBAR/320SQFT C1K STD KING/COMP WIFI/46 LED TV/HRD WD FLRS DESK/MINIBAR/MORN COFFEE DELVRY/208 SQFT AC1 SUITE KNG/COMP WIFI/ACCESIBLE/CTY VIEWS WD FLRS/FRDGE/MICROWAVE/MINIBAR/404 SQFT SU2 SUITE DBL/COMP WIFI/LIVNG RM/CTY VIEWS WD FLRS/FRDGE/MICROWAVE/MINIBAR/404 SQFT ACK STANDARD WHEELCHAIR ACCESSIBLE / 2 QUEEN / DESK / MINIBAR / COMP WIFI / 320 SQFT ACQ STANDARD WHEELCHAIR ACCESSIBLE / 1 QUEEN / DESK / SEATING AREA / WIFI / 208 SQFT C1Q CTY VIEW QUEEN/COMP WIFI/HRD WD FLRS 46 LED TV/DESK/MINIBAR/COMP WIFI/208 SQFStandard Amenities In All RoomsAlarm Clock Bathroom Amenities Bathroom Phone Bathtub and Shower Bathtub Only Cable TV Color TV Direct Dial Electrical Adapters Hair Dryer HSPD Iron Board MiniBar Newspaper Outlet Voltage 220 Phone Two Lines Private Bath Radio Remote TV Safe Shower Only Speaker Phone Stereo Voicemail Work Desk All Other Room Type Amenities

5% Groupon Bucks Credit