59 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Broadway In Chicago

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

July 28, 31 & Aug. 2
 
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
89% (504 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: 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: 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% (303 ratings)
 
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)
 
Source: Chuan Spa at The Langham, Chicago

Save 50% on a luxurious spa package at Chuan Spa at The Langham -- named one of the Best Spas in Chicago by Travel + Leisure.

June 1, 2016 - Aug. 31, 2016; Monday-Thursday
98% (44 ratings)
 
Source: Wateriders

Members save 40% on a fireworks kayak tour from Wateriders that's "a truly one-of-a-kind sightseeing experience" (Travel + Leisure).

Through Sept. 3, 2016; Wednesdays or Saturdays
86% (87 ratings)
 
Source: Chicago Helicopter Experience

See Chicago's famous skyscrapers from a unique perspective with a helicopter tour that takes you over Lake Michigan with unobstructed skyline views.

Through Aug. 31, 2016
100% (26 ratings)
 
Source: Pops for Champagne

"Those who worship the bubbly agree there's no substitute for this first-class purveyor of grand Champagne" (Zagat). Save over 40% on a visit to Pops.

Through Oct. 31, 2016; Sunday-Thursday
 
Source: Kinmont

When this came across our desks in our Chicago office, we couldn't wait to share it with our members -- one of our favorite seafood spots in the city at a discount.

Through Aug. 31, 2016
96% (50 ratings)
 
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
94% (388 ratings)
 
Source: Bike & Roll Chicago

For 50% off, pedal around the streets of Chicago, and explore the city's historic neighborhoods with a half-day bike rental.

Through Sept. 30, 2016
 
Source: Balanced Flow Wellness at Balance Spa - Palmer House A Hilton Hotel

Fodor's praises the "massive" AAA 4-Diamond Palmer House for its prime downtown location and "modern attributes" like the luxurious spa.

Through Nov. 11, 2016
 

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