12 deals from our Canadian site*
* Taxes and fees may be additional.
Source: Chicago's Finest Tours

Our members love tours from Chicago's Finest, telling us "I enjoyed everything about the tour" and "our guide was wonderful." Save 50% off a tour this spring.

Through Aug. 31, 2016
97% (158 ratings)
 
Source: Major Airlines on Fly.com

Travel into October
 

Hotels with Member-Exclusive Extras

 
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: 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

88% (48 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% (138 ratings)
 
Source: Central Loop Hotel


Available year-round

95% (19 ratings)
 
Source: Club Quarters Hotel, Wacker at Michigan


Available year-round

89% (28 ratings)
 
Source: River Hotel


Available year-round

82% (17 ratings)
 
Source: Club Quarters Hotel, Central Loop


Available year-round

78% (46 ratings)
 
48 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: Broadway In Chicago

The show won Tony Awards for Best Choreography and Best Score.

July 28, 31 & Aug. 2
 
Source: Wrigley View Rooftop

Save up to $38 on tickets to see the Chicago Cubs from a rooftop with all-you-can-eat food and drinks, including beer and wine.

Select dates through Aug. 17
 
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
 
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. 7 - Nov. 9
 
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 Oct. 31, 2016
 
Source: The Metropolitan Club of Chicago

Arguably the greatest view from a restaurant in North America, the exclusive Metropolitan Club in the Willis Tower offers members a luxe dinner for two.

June 20, 2016 - Oct. 1, 2016
 
Source: Odyssey Cruises

Save over 40% on a dinner cruise on Odyssey Chicago, a cruise which earns a 4-star rating from TripAdvisor users.

Through Aug. 31, 2016
 
Source: City Winery

Dine at City Winery in the West Loop, "a multifaceted amalgam of all things wine from drinking it to making it" (Zagat), and save 50% on brunch, lunch or dinner.

Through Sept. 15, 2016; Sunday-Thursday
 

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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