12 deals from our Canadian site*
* Taxes and fees may be additional.
Source: Porter Escapes

This quick escape includes round trip airfare, two nights 4-star stay at vintage boutique-style hotel and all applicable taxes & fees.

Depart Nov. 10
 
Source: Major Airlines on Fly.com

Travel into December
 

Hotels with Member-Exclusive Extras

 
Source: The Silversmith Hotel

One block from the public art playground of Millennium Park
Available year-round

100% (18 ratings)
 
Source: Thompson Chicago


Available year-round

100% (18 ratings)
 
Source: Radisson Blu Aqua Hotel, Chicago

Ranked one of the Best Hotels in Chicago in the Conde Nast Traveler Readers’ Choice Awards 2014
Available year-round

100% (12 ratings)
 
Source: Fairfield Inn & Suites Chicago Downtown / Magnificent Mile


Available year-round

87% (53 ratings)
 
Source: Best Western Plus Hawthorne Terrace

Saves 35% with dates into Cubs season, including six home games
Available year-round

100% (11 ratings)
 
Source: IVY Boutique Hotel

A cool boutique hotel within walking distance to many of Chicago’s most popular attractions
Available year-round

96% (141 ratings)
 
Source: Chicago Athletic Association

Stay in a palatial building that was once a private club for the city's elite
Available year-round

96% (83 ratings)
 
Source: Club Quarters Hotel, Wacker at Michigan


Available year-round

90% (30 ratings)
 
Source: River Hotel


Available year-round

83% (18 ratings)
 
Source: Club Quarters Hotel, Central Loop


Available year-round

78% (49 ratings)
 
34 deals from our U.S. site*
* Taxes and fees may be additional.

Deals are priced in U.S. dollars and are sourced by our U.S. Deal Experts. Airfare and air-inclusive vacation or cruise pricing includes taxes; hotel, entertainment, car rental, cruise and Local Deal prices do not include tax, and you may need to pay some tax directly to the provider.

Source: Central Loop Hotel

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
95% (20 ratings)
 
Source: Joffrey Ballet

Tickets start at just $33 per show for orchestra seats.

Various dates 2016-2017
 
Source: American & United Airlines on Fly.com

October-January
 
Source: Chicago Trolley & Double Decker Co.

These open-top, double-decker buses earn a 4-star rating from both TripAdvisor and Yelp users and transport riders through Chicago with guided narration.

Through Dec. 31, 2016
 
Source: Virgin America

Snag discounted fares on the 'Best Domestic Airline' for the ninth year in a row (Travel + Leisure World's Best Awards)

Oct. 18 - Dec. 14
 
Source: Virgin America

Grab a seat for summer and jet across the country on the 'Best Domestic Airline.'

Oct. 18 - Dec. 14
 
Source: JetBlue Airways

Oct. 11 - Jan. 24
 
Source: Skydeck Chicago

Soar to the top of one of America's tallest buildings and see Chicago from 103 stories above street level with this offer that saves over 20% on admission.

Through Feb. 28, 2017
 

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Greg Kunstler — Travel, Entertainment and Local Deal Expert
Greg Kunstler
Deal Expert, Toronto
Here are some I can no longer live without. More