14 deals from our Canadian site*
* Taxes and fees may be additional.
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% (56 ratings)
 
Source: Major Airlines on Fly.com

Travel into November
 

Hotels with Member-Exclusive Extras

 
Source: The Silversmith Hotel

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

100% (17 ratings)
 
Source: Thompson Chicago


Available year-round

100% (18 ratings)
 
Source: Hotel Chicago Downtown

45% savings at a hip, high-energy hotel adjacent to Chicago's House of Blues
Available year-round

93% (68 ratings)
 
Source: Wyndham Grand Chicago Riverfront

This CAA 4-Diamond hotel has a convenient riverfront location a block from Magnificent Mile
Available year-round

96% (410 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

86% (50 ratings)
 
Source: Best Western Plus Hawthorne Terrace

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

100% (10 ratings)
 
Source: IVY Boutique Hotel

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

96% (140 ratings)
 
Source: Chicago Athletic Association

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

98% (81 ratings)
 
Source: Club Quarters Hotel, Wacker at Michigan


Available year-round

90% (29 ratings)
 
Source: River Hotel


Available year-round

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


Available year-round

79% (48 ratings)
 
38 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: 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% (56 ratings)
 
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% (19 ratings)
 
Source: FirstMerit Bank Pavilion at Northerly Island

Save up to 50% on tickets and hear hits like "Worth It," "Work From Home" and "Sledgehammer"

Wednesday, Aug. 31, at 7 p.m.
 
Source: United & American Airlines on Fly.com

September-December
 
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
 
Source: Seadog Cruises

Race across the waters of Lake Michigan this summer, or take an architectural cruise down the Chicago River with the top-rated Seadog Cruises team.

Through Sept. 30, 2016
 

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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