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

The show has garnered overwhelmingly positive critical response, including nine Tonys and a Grammy.

Select dates July 1-24
 
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% (1936 ratings)
 
Source: City Winery

Visit 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 Aug. 15, 2016; Sunday-Thursday
89% (490 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% (177 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: 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% (281 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% (198 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
100% (37 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% (21 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% (47 ratings)
 
Source: Chicago Sailboat Charters

Sailing the waters of Lake Michigan for more than a decade, Chicago Sailboat Charters earns a perfect 5 stars on Yelp for its first-class trips.

May 15, 2016 - Sept. 15, 2016
 
Source: Rittergut Wine Bar & Social Club

Save 35% on a night at Rittergut Wine Bar & Social Club, a riverside hideaway named one of the city's Best Wine Bars by CBS Chicago.

Through Sept. 8, 2016
91% (660 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: 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: Inside Chicago Walking Tours

Save over 30% on your choice of walking tour at Inside Chicago Walking Tours, which earns a perfect 5-star rating from TripAdvisor and Yelp users.

Through Dec. 31, 2016
 
Source: CityPASS Chicago

Get a taste of all Chicago has to offer and save more than 50% on admission to the city's top attractions.

Valid for 9 days; redeem for CityPASS by Feb. 28, 2017
96% (196 ratings)
 

Compare Hotel Rates