1. Home
  2. Hotels
  3. Chicago & Midwest

Best Chicago & Midwest Hotel Deals

$119 & up -- Cleveland: Brand New 4-Star Hotel Downtown
Source: The Westin Cleveland Downtown | By Metra Farrari

Recently completed a $70 million renovation with brand-new guest rooms and on-site steakhouse.
Many dates through December

More »
Source: Grand Geneva Resort & Spa

Enjoy a fall foliage or ski trip at this family-friendly resort
Through Jan. 30

95% (65 Ratings)
Source: Hotel Julien

Close to the Riverboat Museum, National Mississippi River Museum and Aquarium and National Rivers Hall of Fame
Oct. 1, 2014 - Feb. 28, 2015

97% (1181 Ratings)
Source: The Westin Michigan Avenue

This 4-star hotel is close to the city's best shopping and dining.
Select dates Nov. 23 - Jan. 10; +$100 Oct. 1 - Nov. 22

Source: Mission Point Resort, Mackinac Island

Escape to Mackinac Island to savor the final days of pleasant weather before winter hits
Select weekdays Sept.-Oct.; +$20 weekends

Source: The Osthoff Resort

Soak up views of autumn foliage around Lake Elkhart from a balcony room
Sundays-Thursdays Nov. 1 - Dec. 30; +$20 weekends

100% (80 Ratings)
Source: Travelzoo

Chicago hotels with extras exclusive to Travelzoo
Available daily

Source: Sheraton St. Louis City Center Hotel & Suites

Visit the "Gateway to the West" and stay close to all the city's main attractions
Select dates Nov. 23 - Jan. 5; surrounding dates +$50

Source: 816 Hotel

Discover why this hotel is "breaking the mold in Kansas City" with a deal that includes $30 massage credit and breakfast for two.
Travel through February 2015

Source: West Bay Beach, A Holiday Inn Resort

Head to one of the "10 Best Small Towns in America" and stay at the No. 2 ranked resort in Traverse City on TripAdvisor.
Daily through Dec. 30

100% (18 Ratings)

More Deals on Chicago & Midwest Hotels

Nov. 23-27; Dec. 14-18, 21-26
Dana Hotel & Spa
Sundays-Thursdays through Oct. 30
The Cheshire
Sundays-Thursdays through Oct. 30
Seven Gables Inn
Deals through November
Featured Destination: Chicago

Compare Multiple Travel Sites in One Search

From: To: Travelers:
Depart: Return: One-way
Enter city: Guests:
Check-in: Check-out: Rooms:
From: To: Travelers:
Depart: Return: Rooms:
Enter city: Pick-up Time:
Pick-up Date: Return Date: Return Time: