1. Home
  2. Hotels
  3. Chicago & Midwest

Chicago & Midwest Hotel Deals

New! Search Hotels by Date

Top Deals

$149 -- Ohio: Put-In-Bay Getaway for 4 w/Breakfast & Credit
Source: Put-in-Bay Resort and Conference Center | By Metra Kootsikas

Grab three friends and head to Put-in-Bay, described the "Key West of Lake Erie." Travelzoo members can choose between two resort and exclusively save
Travel midweek, May-June and Aug. 24-Oct. 22

More »
Source: Wyndham Grand Riverfront

Visits during Chicago's most coveted season are discounted up to 40% at this hotel, with an automatic room upgrade for stays into summer.
Select dates through Sept. 7

96% (221 ratings)
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: 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: 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% (1100 ratings)
Source: The Westin Michigan Avenue

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.
Select Friday-Saturday stays through August; midweek +$100

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 August

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 August


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