14 deals from our Canadian site*
* Taxes and fees may be additional.
Source: Flight Centre

Save up to $1000 on WestJet vacations with air to some of the most popular U.S. destinations from across Canada.

Into December
 
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% (155 ratings)
 
Source: Major Airlines on Fly.com

Travel into August
 

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% (46 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

97% (137 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: Club Quarters Hotel, Central Loop


Available year-round

80% (45 ratings)
 
Source: River Hotel


Available year-round

77% (13 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: Frontier Airlines on Fly.com

August-October
 
Source: United Airlines on Fly.com

August-October
 
Source: United & Spirit Airlines on Fly.com

July-October
 
Source: Frontier Airlines on Fly.com

July to August
 
Source: Park Grill Chicago

Save 45% on a picnic for two from Park Grill to pair with the Millennium Park Summer Film Series at Jay Pritzker Pavilion on Tuesdays this summer.

June 21, 2016 - Aug. 30, 2016; Tuesdays only
 
Source: Wrigley View Rooftop

Phish performs for the first time at Wrigley Field this summer; catch the concert from an all-inclusive rooftop with a view of the stage.

Friday, June 24 & Saturday, June 25
 

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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