1. Home
  2. Hotels
  3. Chicago & Midwest

Chicago & Midwest Hotel Deals

New! Search Hotels by Date

Top Deals

Put-in-Bay 2-Nt. Getaway w/Breakfast & Drinks, Save 40%
 
Source: Put-in-Bay Resort and Bay Lodging Resort | By Karl Klockars

Locals say September and October is the best time to visit this island getaway. Members can save hundreds on a visit with a group.
Through Oct. 24, 2015

More »
94% (33 ratings)
Source: Hotel Vandivort

Head to the "Queen City of the Ozarks" for a night at the new Hotel Vandivort, where members can save over 40% on a stay.
Daily through Oct. 15, 2015

 
Source: Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

These Labor Day weekend rates save you 50% off a stay later in the month, and member perks include discounts on parking.
Most dates between Sept. 3-9

 
Source: The Hotel Minneapolis

Say goodbye to summer with last-minute savings, including Labor Day weekend, at this stately downtown property near Target Field.
Through Sept. 13

94% (17 ratings)
 
Source: Gunflint Lodge

Recently named the Best Wilderness Resort in the State by the Star-Tribune, the Gunflint Lodge offers savings of over 50% on a Northwoods adventure.
Through Dec. 24, 2015; availability varies by season

95% (63 ratings)
 
Source: Member Only Deal

Steal hot last-minute rates at the hip Hard Rock Chicago, saving members up to 30% versus surrounding dates and inclusive of $40 in extras.
Most dates until Sept.13

90% (276 ratings)
 
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

94% (401 ratings)
 
Source: The Westin Michigan Avenue

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.
Many Thursdays-Saturdays Oct. 30 - Dec. 30

 
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 weekends through November

 

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