Flash Deals Groupon-Exclusive Discounts on Top-Rated Travel

Hotel near Chicago's Magnificent Mile
Hotel near Chicago's Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

Chicago

Family-friendly hotel right off of Chicago’s Magnificent Mile; guest rooms have free WiFi and views of the skyline or Lake Michigan

33% Off $99 From $66/night

$99 From $66/night

Friendly Hostel in Chicago Loop
Friendly Hostel in Chicago Loop

Hostelling International Chicago

Chicago

Environmentally conscious hostel in Chicago’s Loop offers complimentary breakfast, free WiFi, and tours of the city

45% Off $99 From $54/night

$99 From $54/night

Boutique Hotel in Chicago's South Loop
Boutique Hotel in Chicago's South Loop

Chicago South Loop Hotel

Chicago

Boutique hotel a short cab ride from McCormick Place, the Museum Campus, and other downtown Chicago attractions; free parking

37% Off $89 From $56.07/night

$89 From $56.07/night

Private Room in Lincoln Park Hostel
Private Room in Lincoln Park Hostel

Chicago Getaway Hostel

Chicago

Youthful hostel in Park West has complimentary breakfast, free WiFi, and nightly entertainment including live music

36% Off $55 From $35/night

$55 From $35/night

4-Star Hotel in Chicago's River North Area
4-Star Hotel in Chicago's River North Area

The Hotel Chicago

Chicago

Posh 4-star hotel located on the Chicago River, minutes from Millennium Park, the Hancock Observatory, and Museum Campus

53% Off $169 From $79/night

$169 From $79/night

DoubleTree by Hilton in Downtown Chicago
DoubleTree by Hilton in Downtown Chicago

DoubleTree by Hilton Chicago Magnificent Mile

Chicago

Upscale DoubleTree hotel located two blocks from Chicago’s Magnificent Mile and Navy Pier

35% Off $99 From $64/night

$99 From $64/night

4-Star Boutique Hotel in Chicago's Lincoln Park
4-Star Boutique Hotel in Chicago's Lincoln Park

Hotel Lincoln

Chicago

4-star boutique hotel overlooking Lincoln Park has chic guest rooms, rooftop lounge, and skyline views

30% Off $109 From $76/night

$109 From $76/night

Wyndham Suites in Chicago Suburb
Wyndham Suites in Chicago Suburb

Wyndham Glenview Suites

Chicagoland

Spacious suites at Wyndham hotel with free shuttle to local attractions and trains to Chicago

37% Off $99.99 From $62.71/night

$99.99 From $62.71/night

2-Night Stay in Modern Cottages near Lake Michigan
2-Night Stay in Modern Cottages near Lake Michigan

Bluewater Vacation Rentals

South Haven, MI

Spacious harborside cottages with gourmet kitchens and fireplaces near Lake Michigan

15% Off $350 $298

$350 $298

Romantic Suites in Chicago Suburbs
Romantic Suites in Chicago Suburbs

The Champagne Lodge & Luxury Suites

Greater Chicago

Romantic suites located about 30 minutes from downtown Chicago; in-room whirlpool tubs and private spa onsite

49% Off $193 From $99/night

$193 From $99/night

Romantic Whirlpool Suites in Chicagoland Area
Romantic Whirlpool Suites in Chicagoland Area

Sybaris Pool Suites

Downers Grove, IL

A unique couples-only retreat in Chicagoland with whirlpools in each room, fireplaces, and romantic extras

38% Off $209 $129

$209 $129

Biggest Loser Resort Chicago Weight-Loss Program
Biggest Loser Resort Chicago Weight-Loss Program

Biggest Loser Resort Chicago

Bloomingdale, IL

Learn to adopt healthy habits with fitness classes and nutrition education in a supportive environment at this Biggest Loser Resort

40% Off $2,995 $1,797

$2,995 $1,797

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, IL

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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.

5% Credit

Park Hyatt Chicago
Park Hyatt Chicago
Chicago, IL

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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.

5% Credit

Palomer Hotel
Palomer Hotel
Chicago, IL

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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.

5% Credit

The Wit Hotel Chicago
The Wit Hotel Chicago
Chicago, IL

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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.

5% Credit

Ivy Boutique Hotel
Ivy Boutique Hotel
Chicago, IL

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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.

5% Credit

The Lobby
The Lobby
Chicago, IL

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

5% Credit

Chicago South Loop Hotel
Chicago South Loop Hotel
Chicago, IL

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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.

5% Credit

Wyndham Grand Chicago Riverfront
Wyndham Grand Chicago Riverfront
Chicago, IL

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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.

5% Credit

dana hotel and spa
dana hotel and spa
Chicago, IL

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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.

5% Credit

4-Star Mystery Hotel
4-Star Mystery Hotel
Chicago, IL

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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.

5% Credit

Chicago Marriott Midway
Chicago Marriott Midway
Chicago, IL

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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.

5% Credit

Hard Rock Hotel Chicago
Hard Rock Hotel Chicago
Chicago, IL

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With a stay at Hard Rock Hotel Chicago, you'll be centrally located in Chicago, minutes from Bridgehouse and Chicago River Museum and Millennium Park. This 4-star hotel is close to Art Institute of Chicago and Skydeck Ledge.

5% Credit

Renaissance Chicago Downtown Hotel
Renaissance Chicago Downtown Hotel
Chicago, IL

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With a stay at Renaissance Chicago Downtown Hotel, you'll be centrally located in Chicago, steps from Vietnam Veterans Memorial and Chicago Theater. This family-friendly hotel is close to Art Institute of Chicago and Skydeck Ledge.

5% Credit

Kinzie Hotel
Kinzie Hotel
Chicago, IL

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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.

5% Credit

Ramada Inn Lake Shore
Ramada Inn Lake Shore
Chicago, IL

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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.

5% Credit

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

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A stay at Embassy Suites Chicago Downtown - Lakefront places you in the heart of Chicago, walking distance from Arts Club of Chicago and Tribune Tower. This family-friendly hotel is close to Millennium Park and Art Institute of Chicago.

5% Credit

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

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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.

5% Credit

Club Quarters, Wacker at Michigan
Club Quarters, Wacker at Michigan
Chicago, IL

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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.

5% Credit

Hotel Lincoln
Hotel Lincoln
Chicago, IL

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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.

5% Credit

Waldorf Astoria Chicago
Waldorf Astoria Chicago
Chicago, IL

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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, IL

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A stay at Raffaello Hotel places you in the heart of Chicago, steps from Broadway Playhouse and Hancock Tower. This 4-star hotel is close to Millennium Park and Art Institute of Chicago.

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Courtyard Chicago Downtown/River North
Courtyard Chicago Downtown/River North
Chicago, IL

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With a stay at Courtyard by Marriott Chicago Downtown River North, you'll be centrally located in Chicago, steps from American Medical Association Headquarters and minutes from Wrigley Building. This family-friendly hotel is close to Hancock Tower and Art Institute of Chicago.

5% Credit

Hotel Burnham, a Kimpton Hotel
Hotel Burnham, a Kimpton Hotel
Chicago, IL

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With a stay at Hotel Burnham, a Kimpton Hotel, you'll be centrally located in Chicago, steps from Picasso Statue and Ford Center for the Performing Arts Oriental Theatre. This 4-star hotel is close to Art Institute of Chicago and Skydeck Ledge.

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

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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, IL

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A stay at Hotel Indigo Chicago Downtown Gold Coast places you in the heart of Chicago, minutes from Newberry Library and Hancock Tower. This family-friendly hotel is close to Millennium Park and Art Institute of Chicago.

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DoubleTree by Hilton Chicago Magnificent Mile
DoubleTree by Hilton Chicago Magnificent Mile
Chicago, IL

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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% Credit

Chicago Marriott Dtwn Magnificent Mile
Chicago Marriott Dtwn Magnificent Mile
Chicago, IL

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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.

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

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With a stay at Marriott Chicago at Medical District/UIC in Chicago (The Loop - Downtown), you'll be convenient to UIC Pavilion and University of Illinois Chicago. This hotel is close to Skydeck Ledge and Willis Tower.

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

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With a stay at The Palmer House Hilton, you'll be centrally located in Chicago, steps from Bank of America Theatre and Haskell Building. This 4-star hotel is close to Millennium Park and Willis Tower.

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Hotel Allegro Chicago, a Kimpton Hotel
Hotel Allegro Chicago, a Kimpton Hotel
Chicago, IL

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With a stay at Hotel Allegro, a Kimpton Hotel, you'll be centrally located in Chicago, steps from Cadillac Palace Theatre and Chicago City Hall. This 4-star hotel is close to Willis Tower and Millennium Park.

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