8 deals from our UK site
Source: Ocean Florida

We've never seen a Chicago break on the site before, but this was worth waiting for

Select dates 17 Jan-21 Feb
 

Hotels with Member-Exclusive Extras

 
Source: Hotel Chicago Downtown

Hip, high-energy hotel adjacent to Chicago's House of Blues
Available year-round

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

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

96% (408 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: 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: 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: Central Loop Hotel

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

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

A whisker away from the shopping mecca of Magnificent Mile
Available year-round

89% (28 ratings)
 
54 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 holidays or cruise pricing includes taxes; hotel, entertainment, car hire, cruise and Local Deal prices do not include tax, and you may need to pay some tax directly to the provider.

Source: Sofitel Chicago

Travel between Aug. 2016 - Jan. 2017
 
Source: Hotel Lincoln

Members can lock in exclusive savings through 2016 at this Lincoln Park spot, named one of Chicago's Best Boutique Hotels (Travel + Leisure).

Select weekdays throughout 2016
 
Source: American & United Airlines on Fly.com

August-December
 
Source: Frontier Airlines on Fly.com

August-December
 
Source: Broadway In Chicago

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

July 28, 31 & Aug. 2
 
Source: Cirque du Soleil

"TORUK -- The First Flight" is a new Cirque du Soleil show inspired by the blockbuster movie "AVATAR"

Aug. 3-7
 
Source: Frontier Airlines on Fly.com

August-October
 
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: Virgin America

Fly with more space on the 'Best Domestic Airline' (Travel + Leisure) and receive complimentary drinks, food and entertainment

Aug. 16 - Sept. 28
 
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
 

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