Best Chicago Last Minute Deals*

*Some taxes, fees extra. Vacation & cruise rates are per person with double occupancy, unless noted.
$156-$206 -- Chicago: Well-Reviewed Loop Hotel in Peak Fall
 
Source: Central Loop Hotel | By Ryan Haase

While other Chicago hotels charge $250 or more in fall, Central Loop Hotel dodges the trend, undercutting many of them by as much as $100
Weekends Aug. 19 - Nov. 26; Dec. is even cheaper

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95% (19 ratings)
Source: CheapCaribbean.com

Fly nonstop from Chicago and spend four nights at a beachfront, AAA 4-Diamond all-inclusive resort
Select dates in September

 
Source: Apple Vacations

Nonstop transfers, airfare from Chicago (O'Hare), a junior suite and seven nights at an all-inclusive Dreams resort are included in this deal
Select dates, August-September

 
Source: Kimpton Hotel Monaco Chicago

Score a great rate just steps from the Mag Mile, the Chicago River and the Loop at one of the best hotels in Chicago: the AAA 4-Diamond Hotel Monaco.
Travel through Jan. 31

100% (52 ratings)
 
Source: Avianca

Book by Aug. 31 for flights into December on Avianca Airlines.
Through Dec. 7

 
Source: Macao Government Tourism Office

Fly from New York, Los Angeles, Houston, San Francisco, Chicago & Seattle on EVA Airways, one of the top 10 airlines (Skytrax)
Sept. 1 - Dec. 11

 
Source: Avis

This exclusive deal is combinable with additional perks like free upgrades, free weekend days or discounts on weekly rentals
Through 2016

 
Source: State House Inn, an Ascend Collection hotel

Save over 50% at this member-favorite hotel with midcentury-modern style; it's a great destination for a Springfield stay full of history.
Daily through Sept. 30, 2016

96% (1612 ratings)
 
Source: Virgin America

Snag discounted fares on the 'Best Domestic Airline' for the ninth year in a row (Travel + Leisure World's Best Awards)
Sept. 13 - Dec. 14

 

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