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Best Chicago & Midwest Hotel Deals

$109 -- Weekends at 4-Star Chicago Airport Hotel w/Breakfast
Source: Hilton Chicago O'Hare | By Metra Farrari

Make flying into and out of the Windy City a breeze with this bed & breakfast package
Weekends in May; +$20 weekends in April

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Source: Hotel Breakers

Stay at the closest resort to Cedar Point amusement park for 40% off current prices.
May 9-22, 26-29; discounted summer dates available

 
Source: The Abbey Resort

Take off for a Lake Geneva-area resort named one of Midwest Living's 45 Resorts We Love.
Sundays-Thursdays through July 31

 
Source: Gunflint Lodge

Get away from it all this spring, summer or fall at Gunflint Lake, where canoeing, fishing and horseback riding are the order of the day
May 1 - October 29

 
Source: Sheraton Chicago Hotel & Towers

Take in top city sights and skyline views from a 4-star Chicago hotel.
Select dates through Sept. 1

 
Source: Trump International Hotel & Tower Chicago

Luxuriate at a 5-star downtown hotel with show-stopping views and a long list of awards, including 'World's Best'
Select dates through July 8

 
Source: Stout's Island Lodge

Retreat to a quiet island in northwest Wisconsin, where nature walks and nights by the bonfire await.
May 9 - Nov. 1

 
Source: The Westin Michigan Avenue

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.
Select dates through July 3

 
Source: The Westin Chicago River North

Check in to a AAA 4-Diamond hotel with a top location and sweeping views of the Chicago river.
Select dates through Aug. 29

 
Source: The Inn at Honey Run

Explore miles of nature trails and sip specially selected wine at an Ohio bed-and-breakfast for 50% off.
Through Aug. 31

 
Source: trivago

Find the lowest prices at hotels across the city, from the Loop to Streeterville and Lincoln Park
Through spring

 

More Deals on Chicago & Midwest Hotels

 
Through August
Wyndham Extra Holidays
 
 
 
 
Select dates through April
Sheraton St. Louis City Center Hotel & Suites
 
 
 
Select dates through June
Hotel Blake
 
Available daily
18 Midwest hotels w/extras exclusively for Travelzoo VIPs
 
 
 
 
 

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Travelzoo Tips

Ashley Hamilton — Travel, Entertainment and Local Deal Expert
Ashley Hamilton
Deal Expert, Chicago
Winter visitors are awarded with fewer crowds and some hot hotel deals. More