2 deals from our Canadian site*
* Taxes and fees may be additional.
Source: Sofitel Chicago Water Tower

Select dates through September 2016
 
Source: IVY Boutique Hotel

This intimate spot -- with just five rooms per floor -- "might be the best-kept secret in town" (Frommer's).

Select dates through April
97% (117 ratings)
 
55 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: IVY Boutique Hotel

This intimate spot -- with just five rooms per floor -- "might be the best-kept secret in town" (Frommer's).

Select dates through April
97% (117 ratings)
 
Source: United Airlines & Spirit Airlines on Fly.com

Feb. 10 - March 9 & April 11 - May 7
 
Source: Spirit Airlines on Fly.com

Through May
 
Source: Spirit Airlines on Fly.com

April-June
 
Source: Major Airlines on Fly.com

Through May 18
 
Source: Broadway In Chicago

Features original Broadway cast member and "Rent" star Anthony Rapp

Select performances Feb. 23 - March 2
 
Source: Virgin America

Fly across the country on Conde Nast Traveler's 'Best U.S. Airline'

Through May 18
 
Source: Amtrak

Book two weeks in advance for the best fares to Reno, San Francisco, Salt Lake City and more.

Through June 17
 
Source: Amtrak

Book two weeks in advance for the best fares to Grand Junction, LA, Seattle and more.

Through June 17
 
Source: Adler Planetarium

Space is freaking awesome. Explore mind-boggling facts about our universe with 45% off a visit to the Adler Planetarium.

Through March 16, 2016; not valid Feb. 13-15
 
Source: The Metropolitan Club of Chicago

Arguably the greatest view from a restaurant in North America, the exclusive Metropolitan Club in the Willis Tower offers members a luxe dinner for two.

Jan. 2, 2016 - April 30, 2016
 
Source: Oxygen Spa Studio

Our members praise their trips to Oxygen Spa Studio in the West Loop -- 96% of nearly 140 Travelzoo guests loved their treatments.

Through Feb. 29, 2016
 
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: CityPASS Chicago

Get a taste of all Chicago has to offer and save 50% on admission to the city's top attractions.

Valid 9 days; redeem between March 1, 2015, and Feb. 29, 2016
 
Source: Dinosaur BBQ Chicago

Save over 30% on dinner for two at Dinosaur BBQ in Lincoln Park, named one of Chicago's Hottest BBQ Joints by Zagat.

Through Feb. 29, 2016; Monday-Thursday
 
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: Belly Shack

"So inventive and it all works" Zagat reviewers say of the "always tasty, never boring fare" at Belly Shack. Save nearly 40% on your dining experience.

Through March 31, 2016
 
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
 

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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