9 deals from our Canadian site*
* Taxes and fees may be additional.
Source: Major Airlines on Fly.com

Travel into February
 

Hotels with Member-Exclusive Extras

 
Source: Fairfield Inn & Suites Chicago Downtown / Magnificent Mile


Available year-round

86% (35 ratings)
 
Source: Best Western Plus Hawthorne Terrace

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

100% (5 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: Thompson Chicago


Available year-round

 
Source: Central Loop Hotel

Located in the center of The Loop in the heart of Chicago’s business district
Available year-round

96% (24 ratings)
 
Source: Club Quarters Hotel, Wacker at Michigan


Available year-round

90% (31 ratings)
 
Source: River Hotel


Available year-round

89% (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

 
45 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: Warwick Allerton Hotel Chicago

Guests save up to 60% on a stay this winter, including premium Wi-Fi (reg. $20).

Through March 31
91% (32 ratings)
 
Source: Sofitel Chicago Magnificent Mile

Through March 31
 
Source: The Omni Chicago Hotel

The "modern, comfortable" (Fodor's) Omni Chicago on Michigan Avenue offers discounted rates on suite stays with dining credits & discounted parking.

Through March 31
98% (200 ratings)
 
Source: Wyndham Grand Chicago Riverfront

Shopping, parks, theaters and Chicago River views are basically at your front door with a stay at this hotel steps from the Loop and the Mag Mile.

Through March 31
94% (134 ratings)
 
Source: American Blues Theater

The Chicago Tribune calls it "a warm, inclusive and festive experience."

Through Dec. 31
 
Source: Virgin America

This airline was named Best U.S. Airline for the ninth year in a row in the 2016 Conde Nast Traveler Readers' Choice Awards

Dec. 21 - March 11
 
Source: Virgin America

This airline was named Best U.S. Airline for the ninth year in a row in the 2016 Conde Nast Traveler Readers' Choice Awards

Dec. 21 - March 11
 
Source: Virgin America

This airline was named Best U.S. Airline for the ninth year in a row in the 2016 Conde Nast Traveler Readers' Choice Awards

Dec. 21 - March 11
 
Source: Virgin America

This airline was named Best U.S. Airline for the ninth year in a row in the 2016 Conde Nast Traveler Readers' Choice Awards

Dec. 21 - March 11
 
Source: Virgin America

This airline was just named Best U.S. Airline for the ninth year in a row in the 2016 Conde Nast Traveler Readers' Choice Awards

Dec. 21 - March 11
 
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