1. Home
  2. Hotels
  3. Chicago & Midwest

Chicago & Midwest Hotel Deals

New! Search Hotels by Date

Top Deals

$129-$189 -- Chicago: 4-Star Michigan Avenue Hotel, Save 30%
 
Source: The Westin Michigan Avenue | By Metra Kootsikas

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.
Select dates through April; Other dates from $218

More »
Source: Audubon Inn

Only an hour's drive from Madison and Milwaukee, a cozy getaway awaits at a charming boutique hotel.
Travel Sunday-Friday through Sept. 30, 2015

100% (25 ratings)
 
Source: Hyatt Regency McCormick Place

Check out some of the best views of Lake Michigan and the Chicago skyline this summer.
April 20-22, 26-30; May 8-9, 21-27; Sept. 1-9

 
Source: Hilton Chicago/Oak Brook Hills Resort & Conference Center

Stay at TripAvisor's No. 1-rated hotel in Oak Brook, a quiet retreat not far from downtown Chicago and save 50% exclusively through Travelzoo.
Travel options through October 31

 
Source: Timber Ridge Lodge & Waterpark

Save 30% on peak spring and summer dates and receive four water park passes each day.
Sun.-Fri. May-June; +$20 July 1 - Aug. 28

100% (14 ratings)
 
Source: St. Louis City Center Hotel

Save 40% this spring at a landmark hotel in the heart of Gateway City, with dates including four Cardinals home games.
Travel select dates through June

86% (7 ratings)
 
Source: State House Inn

Visit the Old State Capitol, where Lincoln announced, "A house divided against itself cannot stand" in the days leading up to the Civil War.
Thursdays-Sundays through June

97% (1081 ratings)
 
Source: The Farm LLC

Spend two nights getting a true farm experience, exploring the Kentucky Bourbon Trail or taking a golf getaway.
Travel through Oct. 1, 2015

 
Source: The Westin Indianapolis

Ranked one of the best downtowns in the U.S., plan a 2015 road trip to Indianapolis.
Most Fridays-Saturdays through May

 
Source: The Westin Cleveland Downtown

Including weekends and holidays, book a stay at a new Westin in the heart of downtown.
Most Friday-Saturdays through May

 

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:

Travelzoo Tips

Kristyn Schiavone — Travel, Entertainment and Local Deal Expert
Kristyn Schiavone
Deal Expert, Chicago
Here are some of the best values I’ve found at Navy Pier. More