1. Home
  2. Hotels
  3. Chicago & Midwest

Chicago & Midwest Hotel Deals

New! Search Hotels by Date

Top Deals

$219-$239 -- Chicago: 4-Star Michigan Avenue Hotel, Save 40%
Source: The Westin Michigan Avenue | By Carina Stebbins

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

More »
Source: Bay Lodging Resort

Save on a stay at Put-In-Bay, where "no matter the agenda, everyone’s on island time, Ohio-style" (Travel + Leisure)
July 1, 2015 - Sept. 30, 2015; Sunday-Thursday

Source: The Westin Indianapolis

Ranked one of the best downtowns in the U.S., plan a 2015 road trip to Indianapolis.
Select Friday and Saturday stays through November

Source: The Westin Cleveland Downtown

Within blocks of the Rock & Roll Hall of Fame, book a stay this summer at a Westin Hotel.
Most Friday-Saturdays through Oct.

Source: State House Inn

This is a perfect destination for a summer road trip full of history. Members save nearly 50% on a visit including passes to the Lincoln Museum.
Daily through Sept. 30, 2015

97% (1192 ratings)
Source: Fairfield Inn & Suites Chicago Downtown/Magnificent Mile

Score discounted midweek rates and exclusive Travelzoo extras at this downtown Chicago hotel, just two blocks from Michigan Avenue.
Sundays-Thursdays in August

88% (17 ratings)
Source: Lodge of Four Seasons

Road trip to the Lake of the Ozarks this summer, where families can take in shimmering lake views; all offers include breakfast and a resort credit.
Through Oct. 25, 2015

90% (299 ratings)

More Deals on Chicago & Midwest Hotels

Select dates July - September
Select dates July - September
Most dates August 3-September 7
Club Quarters, Wacker at Michigan
Most dates June 28-July 8
The Ivy Hotel

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:

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