Flash Deals Groupon-Exclusive Discounts on Top-Rated Travel

Chicago Boutique Hotel in Lakeview Neighborhood
Chicago Boutique Hotel in Lakeview Neighborhood

Best Western Plus Hawthorne Terrace

Chicago

After enjoying a free breakfast, explore the theaters, shopping districts, and bars of Chicago’s Lakeview and Boystown neighborhoods

25% Off $99.99 From $74.79/night

$99.99 From $74.79/night

New Chicago Hotel with James Beard–Nominated Bar
New Chicago Hotel with James Beard–Nominated Bar

Freehand Hotel

Chicago

Boutique Chicago hotel with brand-new, James Beard–nominated cocktail and pay-as-you-go guided tours on Saturday mornings

19% Off $78.75 From $64/night

$78.75 From $64/night

19th-Century Hotel in Downtown Chicago
19th-Century Hotel in Downtown Chicago

The Congress Plaza Hotel

Chicago

This 19th-century hotel on Chicago’s Michigan Avenue has hosted several presidents

10% Off $89 From $80.10/night

$89 From $80.10/night

4-Star Riverfront Hotel in Downtown Chicago
4-Star Riverfront Hotel in Downtown Chicago

River Hotel

Chicago

Located along the Chicago River in the Loop, this modern four-star hotel features an Italian bistro and fitness center

25% Off $109 From $81.75/night

$109 From $81.75/night

4-Star Hotel near Chicago's Magnificent Mile
4-Star Hotel near Chicago's Magnificent Mile

MileNorth Hotel ‑ Mag Mile

Chicago

4-star luxury hotel steps from shopping on the Magnificent Mile with a welcoming bar and café; some options include breakfast

41% Off $133.20 From $79/night

$133.20 From $79/night

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

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

28% Off $89 From $64/night

$89 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

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

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

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

30% Off $89.99 From $62.99/night

$89.99 From $62.99/night

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.
Hilton Garden Inn Chicago/Midway Airport
Hilton Garden Inn Chicago/Midway Airport
Bedford Park, Illinois

Get 5% Credit

When you stay at Hilton Garden Inn Chicago/Midway Airport in Chicago, you'll be near the airport and close to Marquette Park and Toyota Park. This hotel is within the vicinity of Morton College and Hawthorne Works Museum.

5% Credit

Hilton Chicago/Oak Lawn
Hilton Chicago/Oak Lawn
Oak Lawn, Illinois

Get 5% Credit

Located in Oak Lawn, Hilton Chicago/Oak Lawn is close to Childrens Museum of Oak Lawn and Chicago Ridge Shopping Mall. This hotel is within the vicinity of Marquette Park and Toyota Park.

5% Credit

Holiday Inn
Holiday Inn
Countryside, Illinois

Get 5% Credit

When you stay at Holiday Inn Chicago - Countryside / Lagrange in Countryside, you'll be close to Creekside Park. This hotel is within the vicinity of Willowbrook Community Park and Brookfield Zoo.

5% Credit

Chicago Marriott Southwest at Burr Ridge
Chicago Marriott Southwest at Burr Ridge
Burr Ridge, Illinois

Get 5% Credit

Located in Burr Ridge, Chicago Marriott Southwest at Burr Ridge is connected to a shopping center and close to Creekside Park and Willowbrook Community Park. This hotel is within the vicinity of National Shrine of St. Therese and Twin Lakes Park.

5% Credit

DoubleTree by Hilton Hotel Chicago - Alsip
DoubleTree by Hilton Hotel Chicago - Alsip
Alsip, Illinois

Get 5% Credit

With a stay at DoubleTree by Hilton Chicago - Alsip in Alsip, you'll be close to Trinity Christian College and Gaelic Park. This hotel is within the vicinity of Chicago Ridge Shopping Mall and Harvey Community Center.

5% Credit

The Hyatt Lodge at McDonald's Campus
The Hyatt Lodge at McDonald's Campus
Oak Brook, Illinois

Get 5% Credit

Located in Oak Brook (Lombard - Oak Brook), The Hyatt Lodge at McDonald's Campus is convenient to Oak Brook Golf Course and Oakbrook Center Mall. This 4-star hotel is within close proximity of York Woods County Forest Preserve and Drury Lane Theater.

5% Credit

Chicago Marriott Oak Brook
Chicago Marriott Oak Brook
Oak Brook, Illinois

Get 5% Credit

With a stay at Chicago Marriott Oak Brook in Oak Brook (Lombard - Oak Brook), you'll be convenient to Oakbrook Center Mall and Drury Lane Theater. This hotel is within close proximity of Oak Brook Golf Course and York Woods County Forest Preserve.

5% Credit

Residence Inn Chicago Oak Brook
Residence Inn Chicago Oak Brook
Oak Brook, Illinois

Get 5% Credit

Located in Oak Brook (Lombard - Oak Brook), Residence Inn by Marriott Chicago Oak Brook is convenient to Oakbrook Center Mall and Oak Brook Golf Course. This hotel is within close proximity of York Woods County Forest Preserve and Drury Lane Theater.

5% Credit

Oak Brook Hills Resort Chicago
Oak Brook Hills Resort Chicago
Oak Brook, Illinois

Get 5% Credit

With a stay at Chicago Oak Brook Hills Marriott Resort in Oak Brook (Lombard - Oak Brook), you'll be close to Ty Warner Park and Yorktown Shopping Center. This golf hotel is within close proximity of Gregg House Museum and Veterans Memorial Park.

5% Credit

Best Western Plus Oakbrook Inn
Best Western Plus Oakbrook Inn
Westmont, Illinois

Get 5% Credit

With a stay at Best Western Plus Oakbrook Inn in Westmont (Lombard - Oak Brook), you'll be convenient to Ty Warner Park and Gregg House Museum. This hotel is within close proximity of Veterans Memorial Park and Oak Brook Golf Course.

5% Credit

Clubhouse Inn & Suites
Clubhouse Inn & Suites
Westmont, Illinois

Get 5% Credit

With a stay at Clubhouse Inn Westmont in Westmont (Lombard - Oak Brook), you'll be convenient to Ty Warner Park and Gregg House Museum. This hotel is within close proximity of Veterans Memorial Park and Oak Brook Golf Course.

5% Credit

Carleton of Oak Park
Carleton of Oak Park
Oak Park, Illinois

Get 5% Credit

Located in Oak Park (Ridgeland), Carleton of Oak Park is minutes from Unity Temple and Madison Street Theatre. This romantic hotel is within close proximity of Ernest Hemingway Museum and House and Frank Lloyd Wright Home and Studio.

5% Credit

Best Western Plus Chicago Hillside
Best Western Plus Chicago Hillside
Hillside, Illinois

Get 5% Credit

Located in Hillside, Best Western Plus Chicago Hillside is close to Stevenson Park and York Woods County Forest Preserve. This hotel is within the vicinity of Oak Brook Golf Course and Drury Lane Theater.

5% Credit

Hyatt Regency Chicago
Hyatt Regency Chicago
Chicago, IL

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

Get 5% Credit

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

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