1. Home
  2. Hotels
  3. Chicago & Midwest

Chicago & Midwest Hotel Deals

New! Search Hotels by Date

Top Deals

$99 -- Chicago 4-Star Hotel incl. Holidays, 40% Off
Source: The Westin Michigan Avenue Chicago | By Carina Stebbins

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.
Many dates Nov. 22 - March 28

More »
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% (302 ratings)
Source: Westin Kansas City at Crown Center

Situated in Hallmark's Crown Center, this hotel offers easy access to 85 acres of shops, restaurants and theaters.
Select dates through September

Source: The Cincinnatian Hotel

Stay at the AAA 4-Diamond Cincinnatian Hotel and exclusively receive daily breakfast for two & daily overnight valet parking.
Travel options through November

93% (367 ratings)
Source: Omaha Embassy Suites - Downtown/Old Market

Stay in the heart of Omaha's Old Market with this exclusive deal that saves $100 on current rates.
Daily Aug. 9 - Oct. 31, 2015

Source: Club Quarters, Central Loop

Just a 15-minute walk from Millennium Park and the iconic Chicago "Bean" sculpture, this Chicago hotel is offering discounted summer weekends.
Fridays-Sundays, Aug. 7 - Sept. 6

Source: Hotel Chicago Downtown

Members can save up to 30% on a stay at the "sleek, modern" Hotel Chicago Downtown, including discounted parking.
Through Oct. 31, 2015

92% (49 ratings)
Source: Sheraton Chicago Hotel & Towers

Take in skyline views from a 4-star Chicago hotel that puts guests in the middle of the downtown action.
Many dates Nov. 22 - Jan 31

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: 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% (1256 ratings)

More Deals on Chicago & Midwest Hotels

Select dates July-September
Select dates September-October

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