9 deals from our Canadian site*
* Taxes and fees may be additional.
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% (154 ratings)
 
Source: Major Airlines on Fly.com

Travel into July
 

Hotels with Member-Exclusive Extras

 
Source: Thompson Chicago


Available year-round

100% (16 ratings)
 
Source: Hotel Chicago Downtown

45% savings at a hip, high-energy hotel adjacent to Chicago's House of Blues
Available year-round

93% (67 ratings)
 
Source: Hotel Lincoln

Save 35% with this deal
Available year-round

96% (101 ratings)
 
Source: Radisson Blu Aqua Hotel, Chicago

Ranked one of the Best Hotels in Chicago in the Conde Nast Traveler Readers’ Choice Awards 2014
Available year-round

100% (12 ratings)
 
Source: Fairfield Inn & Suites Chicago Downtown / Magnificent Mile


Available year-round

87% (45 ratings)
 
Source: Best Western Plus Hawthorne Terrace

Saves 35% with dates into Cubs season, including six home games
Available year-round

100% (9 ratings)
 
Source: IVY Boutique Hotel

A cool boutique hotel within walking distance to many of Chicago’s most popular attractions
Available year-round

97% (137 ratings)
 
38 deals from our U.S. site*
* Taxes and fees may be additional.

Deals are priced in U.S. dollars and are sourced by our U.S. Deal Experts. Airfare and air-inclusive vacation or cruise pricing includes taxes; hotel, entertainment, car rental, cruise and Local Deal prices do not include tax, and you may need to pay some tax directly to the provider.

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
 
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)

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
 
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
 
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
 

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Greg Kunstler — Travel, Entertainment and Local Deal Expert
Greg Kunstler
Deal Expert, Toronto
Here are some I can no longer live without. More