11 deals from our UK site
Source: Infinity Cruises

Includes hotel stays in Chicago & Seattle, plus a 2-night train journey through the Rockies

8, 15 May; 4, 11 Sep, 2017
 
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: The Silversmith Hotel

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

100% (17 ratings)
 
Source: Thompson Chicago

The newly renovated luxury hotel debuted in October 2013
Available year-round

100% (18 ratings)
 
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% (410 ratings)
 
Source: Best Western Plus Hawthorne Terrace

Located in the Lakeview neighbourhood; Wrigley Field, Lake Michigan, Lincoln Park and dozens of restaurants and bars are walkable
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: Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Bargain pick in an upmarket, central neighbourhood
Available year-round

86% (50 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 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: 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% (55 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
 
Source: Skydeck Chicago

Soar to the top of one of America's tallest buildings and see Chicago from 103 stories above street level with this offer that saves over 20% on admission.

Aug. 15, 2016 - Feb. 28, 2017
 
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
 

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