56 deals from our U.S. site*
* Taxes and fees may be additional.
Source: UP Comedy Club

See Chicago veteran improv and sketch performers in "Second City's Improv All-Stars" or "Second City's Fast, Loud & Funny" at UP Comedy Club in Piper's Alley.

Through June 13, 2016; select dates
 
Source: Park Grill Chicago

Save 45% on a picnic for two from Park Grill to pair with the Millennium Park Summer Film Series at Jay Pritzker Pavilion on Tuesdays this summer.

June 21,2016 - Aug. 30, 2016; Tuesdays only
 
Source: Virgin America

Fly across the country on the 'Best U.S. Airline' (Conde Nast Traveler Readers' Choice Awards)

Sept. 7 - Nov. 9
 
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% (176 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% (483 ratings)
 
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: 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 TimeOut.

Through June 30, 2016
 
Source: Kayak Chicago

UPChicago.com calls these guided tours "great water activities for the nature-loving city dweller." Visitors agree: Kayak Chicago earns a 4-star rating on Yelp.

Through June 30, 2016
95% (19 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% (192 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% (14 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
83% (268 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: 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: Lakeview Baseball Club

Save up to $50 on tickets to experience a Chicago Cubs game from a rooftop with an all-inclusive menu, including beer and wine.

Select games through June 21, 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: Wrigley View Rooftop

Save up to $30 on tickets to see the Chicago Cubs from a rooftop with all-you-can-eat food and drinks, including beer and wine.

Select games through June 20
 
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)
 
Source: Hyde Park Brew Fest

The third annual Hyde Park Brew Fest takes place June 4-5, featuring top breweries from around the nation. Members can save over 35% on admission.

June 4-5, 2016; date specific event
 
Source: Chicago's Finest Tours

Our members love tours from Chicago's Finest, telling us "I enjoyed everything about the tour" and "our guide was wonderful." Save 50% off a tour this spring.

Through Aug. 31, 2016
97% (155 ratings)
 
Source: Wrigley View Rooftop

Pearl Jam returns to Wrigley Field this summer; catch the concert from an all-inclusive rooftop with a view of the stage.

Aug. 22 at 7:30 p.m.
 

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