13 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% (157 ratings)
 
Source: Major Airlines on Fly.com

Travel into September
 

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% (67 ratings)
 
Source: Hotel Lincoln

Save 35% with this deal
Available year-round

96% (101 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% (47 ratings)
 
Source: IVY Boutique Hotel

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

97% (137 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: Central Loop Hotel


Available year-round

93% (15 ratings)
 
Source: Club Quarters Hotel, Wacker at Michigan


Available year-round

89% (27 ratings)
 
Source: River Hotel


Available year-round

80% (15 ratings)
 
Source: Club Quarters Hotel, Central Loop


Available year-round

78% (46 ratings)
 
47 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: Major Airlines on Fly.com

August-December
 
Source: Broadway In Chicago

The show has garnered overwhelmingly positive critical response, including nine Tonys and a Grammy.

Select dates July 1-24
 
Source: United & Spirit Airlines on Fly.com

August-September
 
Source: Spa + Fitness Center at Four Seasons Hotel Chicago

The Spa + Fitness Center at Four Seasons Hotel Chicago "makes you feel right at home," raves Forbes Travel Guide. Save over 40% on a relaxing spa day.

Through Sept. 30, 2016; Sunday-Thursday
 
Source: Tall Ship Red Witch

Set a course for Lake Michigan adventure this summer and reserve a trip on the Tall Ship Red Witch. Fireworks sails are select dates this June.

June 22, 25 or 29
 
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: City Winery

Visit 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 Aug. 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