Flash Deals Discounts on Top-Rated Travel

Shop Groupon 4-Star Chicago Hotel near Millennium Park
Staypineapple, An Iconic Hotel, The Loop Chicago
4-Star Hotel in Downtown Chicago
Chicago, IL 2.5 mi
$109 From $92/nt
(11)
Free Cancellation
Shop Groupon 4-Star Hotel in the heart of downtown Chicago
TRENDING
4-Star Top-Secret Chicago Hotel
4-Star Hotel in Chicago
Chicago, IL 3 mi
$179 From $137/nt
(12)
Free Cancellation
Shop Groupon 4.5-Star Luxury Hotel in Chicago's River North
TRENDING
The Godfrey Hotel Chicago
4.5-Star Chicago Hotel
Chicago, IL 3.2 mi
$171 From $90/nt
(154)
Free Cancellation
Shop Groupon Green 4-Star Hotel in Chicago's River North
Hotel Felix Chicago
4-Star Boutique Hotel in Chicago
Chicago, IL 3.2 mi
$119 From $62/nt
(262)
Free Cancellation
Shop Groupon Boutique Hotel near Chicago’s Magnificent Mile
Inn of Chicago
Chicago Boutique Hotel
Chicago, IL 3.3 mi
$88 From $59/nt
(1,636)
Free Cancellation
Shop Groupon Chicago Hotel near Mag Mile Shopping
Chicago Magnificent Mile Hotel
Downtown Chicago Hotel
Chicago, IL 3.3 mi
$117 From $64/nt
(139)
Free Cancellation
Shop Groupon 2.5-Star Hotel near Chicago's Magnificent Mile
2.5-Star Downtown Chicago Hotel
Chicago, IL 3.3 mi
$105 From $59/nt
(226)
Free Cancellation
Shop Groupon 4-Star 1920s Hotel on Chicago's Magnificent Mile
Warwick Allerton Hotel Chicago - Premium Collection
4-Star Downtown Chicago Hotel
Chicago, IL 3.4 mi
$100 From $70/nt
(1,494)
Free Cancellation
Shop Groupon Member Pricing: Hotel near Magnificent Mile
Member Pricing: Hotel near Magnificent Mile
Chicago, IL 3.6 mi
(63)
Price Hidden
Shop Groupon Chicago Hotel near Magnificent Mile
Claridge House
Downtown Chicago Hotel
Chicago, IL 4 mi
$222 From $85/nt
(397)
Free Cancellation
Shop Groupon 4-Star Resort near Shopping at Oak Brook Mall
Hilton Chicago/Oak Brook Hills Resort & Conference Center
4-Star Suburban Chicago Resort
Oak Brook, IL 16.7 mi
$160 From $85/nt
(334)
Free Cancellation
Shop Groupon Romantic Adults-Only Suites in Chicago Suburbs with Champagne
The Champagne Lodge & Luxury Suites
Romantic Hotel near Chicago
Willowbrook, IL 17.3 mi
$173 From $99/nt
(1,668)
Free Cancellation
Shop Groupon Member Pricing: Suburban Inn near Downtown
Member Pricing: Suburban Inn near Downtown
Downers Grove, IL 19.4 mi
(11)
Price Hidden
Shop Groupon DoubleTree Hotel in Chicago's Northwest Suburbs
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
DoubleTree in Suburban Chicago
Itasca, IL 19.8 mi
$119 From $67/nt
(136)
Free Cancellation
Shop Groupon Romantic Chicagoland Suites with Private Pools
Sybaris Pool Suites - Northbrook
Romantic Chicagoland Suites with Private Pools
Northbrook, IL 20.4 mi
(1,201)
$290 $149
Shop Groupon Chicagoland Hotel with Breakfast
Indian Lakes Hotel
Hotel Outside of Chicago
Bloomingdale, IL 24.1 mi
$99 From $80/nt
(811)
Free Cancellation
Shop Groupon DoubleTree near Chicago Suburb's Woodfield Mall
DoubleTree by Hilton Hotel Chicago - Schaumburg
DoubleTree in Suburban Chicago
Schaumburg, IL 24.6 mi
$95 From $65/nt
(172)
Free Cancellation
Shop Groupon 3-Star Hotel near O'Hare Airport
3-Star Top-Secret Buffalo Grove Hotel
3-Star Hotel in Chicago Suburbs
Buffalo Grove, IL 26.8 mi
$87 From $80/nt
(4)
Free Cancellation
Shop Groupon Hotel in Chicago's Northern Suburbs
Hotel in Chicago's Northern Suburbs
Mundelein, IL 32.1 mi
(107)
Price Hidden
Shop Groupon Great Wolf Lodge Water Park Resort in Illinois
Great Wolf Lodge Chicago/Gurnee
Illinois Great Wolf Lodge
Gurnee, IL 39.9 mi
$250 From $119/nt
(986)
Free Cancellation

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.
See More

Market Picks

Shop Groupon Chicago South Loop Hotel
Chicago South Loop Hotel
From $230/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Hyatt Regency McCormick Place
Hyatt Regency McCormick Place
From $155/nt
Chicago, Illinois
Free Cancellation
Shop Groupon The Wheeler Mansion
The Wheeler Mansion
From $180/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Holiday Inn & Suites Chicago - Downtown
Holiday Inn & Suites Chicago - Downtown
From $162/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Chicago Marriott at Medical District/UIC
Chicago Marriott at Medical District/UIC
From $200/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Hotel Blake, an Ascend Hotel Collection Member
Hotel Blake, an Ascend Hotel Collection Member
From $240/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Hilton Chicago- Michigan Ave Cultural Mile
Hilton Chicago- Michigan Ave Cultural Mile
From $245/nt
Chicago, Illinois
Free Cancellation
Shop Groupon The Blackstone, Autograph Collection
The Blackstone, Autograph Collection
From $200/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Crowne Plaza Chicago West Loop
Crowne Plaza Chicago West Loop
From $189/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Congress Plaza Hotel
Congress Plaza Hotel
From $155/nt
Chicago, Illinois
Free Cancellation
Shop Groupon W Chicago - City Center
W Chicago - City Center
From $250/nt
Chicago, Illinois
Free Cancellation
Shop Groupon JW Marriott Chicago
JW Marriott Chicago
From $382/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Central Loop Hotel
Central Loop Hotel
From $104/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Hampton Inn Majestic Chicago Theatre District
Hampton Inn Majestic Chicago Theatre District
From $230/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
From $167/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Kimpton Hotel Allegro
Kimpton Hotel Allegro
From $136/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The Loop
From $180/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Holiday Inn Chicago-Mart Plaza River North
Holiday Inn Chicago-Mart Plaza River North
From $220/nt
Chicago, Illinois
Free Cancellation
Shop Groupon theWit Chicago - a DoubleTree by Hilton Hotel
theWit Chicago - a DoubleTree by Hilton Hotel
From $269/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Renaissance Chicago Downtown Hotel
Renaissance Chicago Downtown Hotel
From $297/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Kimpton Hotel Monaco Chicago
Kimpton Hotel Monaco Chicago
From $189/nt
Chicago, Illinois
Free Cancellation
Shop Groupon The Westin Chicago River North
The Westin Chicago River North
From $199/nt
Chicago, Illinois
Free Cancellation
Shop Groupon St. Jane Chicago
St. Jane Chicago
From $259/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Hotel Chicago Downtown, Autograph Collection
Hotel Chicago Downtown, Autograph Collection
From $140/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Wyndham Grand Chicago Riverfront
Wyndham Grand Chicago Riverfront
From $195/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Club Quarters Hotel, Wacker at Michigan
Club Quarters Hotel, Wacker at Michigan
From $103/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
From $419/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Kinzie Hotel
Kinzie Hotel
From $179/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
From $333/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Trump International Hotel & Tower Chicago
Trump International Hotel & Tower Chicago
From $366/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Hyatt Regency Chicago
Hyatt Regency Chicago
From $200/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Hyatt Place Chicago/River North
Hyatt Place Chicago/River North
From $185/nt
Chicago, Illinois
Free Cancellation
Shop Groupon Courtyard by Marriott Chicago Downtown River North
Courtyard by Marriott Chicago Downtown River North
From $330/nt
Chicago, Illinois
Free Cancellation