67 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: Frontier Airlines on Fly.com

September-October
 
Source: Frontier Airlines on Fly.com

September-October
 
Source: Spirit Airlines on Fly.com

Through July
 
Source: Frontier Airlines on Fly.com

August-October
 
Source: Broadway In Chicago

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

May 10-12
 
Source: Frontier Airlines on Fly.com

August-October
 
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)

May 21 - June 14; Sept. 7 - Nov. 9
 
Source: Starwood Hotels & Resorts

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

Travel many dates through August
 
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% (175 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.

Jan. 4, 2016 - June 30, 2016; dates vary by offer
98% (43 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: 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: 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: 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% (11 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% (182 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
 

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