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Best Chicago & Midwest Hotel Deals

$99 -- Wisconsin: Inn on Woodlake in Kohler incl. Breakfast
Source: Inn on Woodlake | By Travelzoo Staff

A Wine Spectator Award-winning restaurant and other dining options abound near this charming inn.
Sundays-Thursdays, December-April; +$10 weekends

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Source: BookIt.com

This deal includes complimentary evening cocktails, breakfast & Wi-Fi.
Through February

Source: Gunflint Lodge

Get away from it all up north at Gunflint Lake, where skiing, dogsledding and moose calling are the order of the day.
Daily through April 1, 2015

95% (40 ratings)
Source: Hilton Chicago

Ideally located along famed Michigan Avenue, this 4-star hotel is the perfect home base for exploring Millennium Park and the museum campus.
Select dates Dec.-Feb.; Nov.-April also discounted

Source: Magnolia Hotel St. Louis

Explore downtown St. Louis' attractions at this boutique hotel -- newly opened in the historic Mayfair Hotel building -- with this deal of 50% off.
Through Jan. 31, 2015

Source: Seven Gables Inn

Perks at this inn include two drinks and one appetizer from the on-site pub and free valet parking.
Travel through February 2015

Source: Hard Rock Hotel Chicago

Marvel at music memorabilia at this 4-star hotel that is walking distance from the Mag Mile shopping and the theater district.
Travel daily through February

100% (14 ratings)
Source: Argosy Casino, Hotel & Spa

Take a Vegas-style escape and save nearly 50% off at the AAA 4-Diamond Argosy Casino, Hotel & Spa.
Sundays-Thursdays through February 2015

Source: Travelzoo

Chicago hotels with extras exclusive to Travelzoo
Available daily

Source: The Westin Michigan Avenue

This 4-star hotel is close to the city's best shopping and dining.
Select dates Nov. 23 - Jan. 10; +$100 Nov. 1 - Nov. 22

Source: The Westin Cleveland Downtown

Recently completed a $70 million renovation with brand-new guest rooms and on-site steakhouse.
Most dates through February

Source: The Westin Indianapolis

One of The New York Times' top places to go in 2014, visit Indianapolis for the weekend and stay in a recently renovated 4-star hotel.
Weeks of Thanksgiving & Christmas, +$50 surrounding dates


More Deals on Chicago & Midwest Hotels

Nov. 23-30 and Dec. 19-30
Subscriber Only Deal
Deals through November
Featured Destination: Chicago

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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