51 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Major Airlines on Fly.com

August-November, unless otherwise noted
 
Source: Wrigley View Rooftop

Phish performs for the first time at Wrigley Field this summer; catch the concert from an all-inclusive rooftop with a view of the stage.

Friday, June 24 & Saturday, June 25
 
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: 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: 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% (485 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% (176 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: 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% (195 ratings)
 
Source: Chicago Ale Fest

The second annual Chicago Ale Fest takes place June 17-18, featuring top breweries from around the nation. Members can save over 40% on admission.

June 17 & 18
 
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: 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: 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% (273 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: 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% (33 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: 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: 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: 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
 

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