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Chicago & Midwest Hotel Deals

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$99 -- Columbus Hotel w/Zoo Tickets & Breakfast for 2
Source: Crowne Plaza Hotel Columbus | By Monika Zaman

Stay at the newly-renovated Crowne Plaza Columbus - Dublin with this exclusive Travelzoo offer that saves nearly 40% on daily travel.
Daily Oct. 1 - Dec. 31

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Source: Hotel Julien

Experience historic Iowa at the elegant Hotel Julien with this Travelzoo exclusive which includes dining credit, wine tastings and more
Through March 13, 2016

Source: Lake Lawn Resort

Experience southern Wisconsin at this lakefront resort, fresh from a $4 million renovation, with an exclusive Travelzoo deal that includes weekends
Travel through February 4

95% (88 ratings)
Source: The Westin Michigan Avenue

Deals heat up when Chicago cools down -- members can save hundreds on a stay at this 4-Diamond spot during winter months.
Most dates Dec. 13 - Feb. 6

Source: Chula Vista Resort

This top-rated family-centered resort is offering Travelzoo members an exclusive deal that includes water park passes for up to six guests and credit.
Travel Oct. 1 - Dec .17

Source: The Drake Hotel

Save hundreds on a stay at the Drake, which has been on the itinerary of world leaders and international celebrities for decades.
Select dates through March 2016

Source: The Weathervane Inn

Embrace autumn at this romantic waterfront inn and take in stunning views of White Lake while saving up to 50% on a stay.
Travel through Dec. 30

98% (44 ratings)
Source: Grand Geneva Resort & Spa

Members can reserve a restorative stay at the Grand Geneva Resort, one of Wisconsin's rare AAA 4-Diamond destinations.
Sunday-Friday through March 30, 2016

Source: Public Chicago

The most pleasant time of year in the city, at a one of the most fashionable places
Most dates October-November

Source: Timber Ridge Lodge & Waterpark

Members can reserve a night at this Chicago Tribune-praised resort -- including up to six waterpark passes -- along with a dining credit.
Sunday-Friday through March 17; +$30 for Saturdays

Source: Best Western Plus - French Lick

Adventure awaits in French Lick, Ind., this autumn, where Travelzoo members save over 45% on stays at this new, top-rated hotel.
Daily through Dec. 30, 2015

Source: Hotel Alex Johnson

Travelzoo members can take advantage of aggressive autumn pricing that saves 70% on the same rooms in spring at this impressive Rapid City hotel.
Most dates Oct. 25 - Dec. 30

Source: Westin Kansas City at Crown Center

Spend a weekend at this top Kansas City property and save 35% off peak rates.
Most weekends in November-December


Hotels with Member-Exclusive Extras

Source: Wyndham Grand Chicago Riverfront

This hotel underwent a multimillion-dollar redesign in 2013
Available year-round

Member Favorite: 96% (311 ratings)
Source: Warwick Allerton Hotel

Well-priced, central hotel on the Magnificent Mile in the Near North neighborhood
Available year-round

Member Favorite: 100% (25 ratings)
Source: MileNorth, A Chicago Hotel

Renovated in 2012
Available year-round

86% (29 ratings)
Source: dana hotel & spa

A stylish, lively hotel, three blocks from the Magnificent Mile
Available year-round

Member Favorite: 96% (50 ratings)

More Deals on Chicago & Midwest Hotels

Through October; Click to see more
American Express Travel

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