1. Home
  2. Hotels
  3. Chicago & Midwest

Best Chicago & Midwest Hotel Deals

$149-$189 -- Cleveland: Brand New 4-Star Hotel Downtown
Source: The Westin Cleveland Downtown | By Mary Walker Baus

Recently completed a $70 million renovation with brand-new guest rooms and on-site steakhouse
Select dates through October

More »
Source: Heidel House Resort

Spend the dog days of summer or colorful days of fall in this quaint lake town just 90 minutes from Milwaukee or Madison
Through Dec. 30

 
Source: Sheraton Bloomington Hotel

Stay at a AAA 4-Diamond property this summer that saves 50% on similar hotels in the area
Aug. 24 - Sept. 7

 
Source: The Weathervane Inn

All rooms have a Jacuzzi and a fireplace; warm chocolate chip cookies are served every evening
Travel Sept. 1, 2014 - Dec. 31, 2014

 
Source: Sheraton Chicago Hotel & Towers

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

 
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 November

 
Source: The Westin Michigan Avenue

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile
Select dates through Nov. 22

 
Source: State House Inn

Learn in the "Land of Lincoln" with half off a package at the State House Inn, including museum tickets, drinks, parking and Wi-Fi.
June 18, 2014 - Oct. 31, 2014

97% (728 Ratings)
 
Source: Kimpton Hotels

These hotels are in the heart of Chicago and offer a nightly complimentary wine hour.
Select dates through October

 
Source: The Westin Chicago River North

Check in to a AAA 4-Diamond hotel with sweeping views of the Chicago River
Select dates through December

 

More Deals on Chicago & Midwest Hotels

 
 
 
 
 
 
Select Sundays-Thursdays through August
Hotel for Travelzoo VIPs
 
Available daily
18 Midwest hotels w/extras exclusively for Travelzoo VIPs
 
Deals through November
Featured Destination: Chicago
 

Compare Multiple Travel Sites in One Search

From: To: Travelers:
Depart: Return: One-way
Round-trip   
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: