46 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Chicago Athletic Association

With great bars, top restaurants and an amazing rooftop view, the Chicago Athletic Association hotel is one of our favorite stays in the city.

Travel through May 9
97% (66 ratings)
 
Source: Broadway In Chicago

"Chicago" is the longest-running American musical in Broadway history.

May 10-12
 
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. 20 & 22 at 7:30 p.m.
 
Source: Wrigley View Rooftop

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

Thursday, June 30 at 7 p.m.
 
Source: Virgin America

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

Sept. 7 - Nov. 16
 
Source: Starwood Hotels & Resorts

Get ready for summer in the Windy City with the best rates from three upscale Starwood hotels.

Travel through Labor Day
 
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 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: Wrigley View Rooftop

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

Select dates through May 15, 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
90% (481 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% (186 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% (12 ratings)
 
Source: mEAT - Streeterville

Carnivores, take note -- members can order anything off the menu at the appropriately named mEAT in Streeterville and save over 40%.

Through May 31, 2016
92% (48 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: 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: Wateriders

Members save up to $25 on a fireworks kayak tour from Wateriders that's "a truly one-of-a-kind sightseeing experience" (Travel + Leisure).

Through Aug. 24, 2016
86% (87 ratings)
 
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 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% (267 ratings)
 
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% (659 ratings)
 
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