65 deals from our U.S. site*
* Taxes and fees may be additional.
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
96% (101 ratings)
 
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: Sofitel Chicago

Travel between Aug. 2016 - Jan. 2017
98% (59 ratings)
 
Source: American Airlines on Fly.com

August-November
 
Source: Frontier Airlines on Fly.com

August-October
 
Source: American & Frontier Airlines on Fly.com

September-December
 
Source: American Airlines on Fly.com

August-November
 
Source: Frontier Airlines on Fly.com

August-December
 
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
93% (1975 ratings)
 
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
98% (46 ratings)
 
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
90% (507 ratings)
 
Source: Pizzeria UNO

Pizzeria UNO is where Chicago's iconic deep dish pizza was created over 70 years ago. With this exclusive offer, members can learn to craft their own.

Through Aug. 31, 2016; Tuesday-Sunday mornings
98% (181 ratings)
 
Source: Chicago Explorer Pass

Get a taste of all Chicago has to offer, and save up to 40% on the gate prices to over 25 of the city's top attractions with the Chicago Explorer Pass.

Valid for use through March 31, 2017
84% (304 ratings)
 
Source: Museum of Contemporary Art Chicago

Travelzoo members save 25% on admission to the Museum of Contemporary Art, one of Chicago's best museums, according to Chicagoist and Time Out.

Through May 31, 2017
 
Source: Mystic Blue

Save over 30% on a two-hour Boathouse cruise on Mystic Blue this summer.

June 20, 2016 - Aug. 30, 2016
98% (46 ratings)
 
Source: Oxygen Spa Studio

Our members praise their trips to Oxygen Spa Studio in the West Loop -- 97% of nearly 200 Travelzoo members loved their treatments.

Through Aug. 31, 2016
97% (203 ratings)
 

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