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Best Chicago & Midwest Hotel Deals

$85-$99 -- Wisconsin: 4-Star Lake Geneva Resort, 50% Off
Source: Grand Geneva Resort & Spa | By Jen Lee

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

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95% (65 Ratings)
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: 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: Sheraton Chicago Hotel & Towers

Stay over the holidays at this hotel near Navy Pier
Select dates through December

 
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)
 
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 through December

 

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
 

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