51 deals from our U.S. site*
* Taxes and fees may be additional.
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.

June 1, 2015 - Sept. 30, 2015
 
Source: Randolph Street Market

With dozens of vendors offering antiques, clothing, global goods and gourmet foods, Randolph Street Market is one of the nation's top shopping destinations.

Through Dec. 13, 2015; valid for events on specific dates
 
Source: Bliss Chicago

Unwind at Bliss Chicago inside the W on Lake Shore Drive with your choice of spa treatments and save 50%.

Through Sept. 30, 2015; Monday-Friday
 
Source: Medieval Times

Dine like royalty on a four-course feast and save over 40% with this offer for the jousting and sword-fighting show at Medieval Times in Schaumburg.

Valid for use through Sept. 7, 2015
 
Source: Glowout

Get ready for a night on the town with a blowout or a mani/pedi at Glowout, which earns a perfect 5 stars on Yelp from over 100 reviewers.

Through Aug. 30, 2015
 
Source: Urban Kayaks

See the city from a unique water-based vantage point this summer on a Chicago River kayak trip from Chinatown with the top-rated Urban Kayaks.

Through Sept. 5, 2015; trips run Friday-Sunday
 
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 summer.

June 1, 2015 - Oct. 31, 2015
 
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. 28, 2015; Tuesday-Saturday mornings
 
Source: Mart Anthony's Italian Restaurant

Travelzoo members can save 55% at Mart Anthonys, where "the atmosphere is great, the food is superb and the service is outstanding" (10Best).

Through Aug. 31, 2015
 
Source: Balance Spa & Fitness at Palmer House a Hilton Hotel

Fodor's praises the "bustling and massive" AAA 4-Diamond Palmer House for its "hard to beat" location and "modern attributes" like the luxurious Balance Spa.

Through Dec. 11, 2015; Monday-Friday
 
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: Headquarters Beercade River North

Sip beers and score points at Headquarters Beercade in River North this summer. Travelzoo members save up to 50% on a visit to this critically praised arcade bar.

Through Aug. 31, 2015
 
Source: Macku Sushi

Let Michelin-praised chef Macku Chan and his acclaimed kitchen create six courses for you, along with a signature cocktail, for more than 40% off.

Through Aug. 30, 2015
 
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 Nov. 18, 2015
 
Source: Old Fifth

RedEye says Old Fifth, featuring a "dynamic duo" of pizza and whiskey, "should be at the top of your list" for pies made with a "sweeter sauce with a bit of spice."

Through Oct. 31, 2015
 
Source: Usagi Ya Sushi

The 2013 Michelin Guide says that the Usagi Ya menu "shines with its unorthodox combinations." Members save more than 50% on this four-course dinner.

Through Nov. 10, 2015
 
Source: Headquarters Beercade Lakeview

Sip beers and score points at Headquarters Beercade in Lakeview this summer. Travelzoo members save up to 50% on a visit to this critically praised arcade bar.

Through Aug. 31, 2015
 
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 sailboat trips.

May 15, 2015 - Sept. 15, 2015
 
Source: Uptown Underground

Save over 50% on a night out at Uptown Underground, a "subterranean hang that features decorative nods to Prohibition" (Zagat).

Through Oct. 30, 2015
 
Source: SeaBreeze Charter

Save up to 50% on a two-hour private charter for up to six passengers, cruising out of Monroe Harbor near Millennium Park and Buckingham Fountain.

May 16, 2015 - Sept. 15, 2015; dates vary by voucher
 
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Travelzoo Tips

Anna Heinemann — Travel, Entertainment and Local Deal Expert
Anna Heinemann
Deal Expert, Chicago
So get your travel dates set and start planning early for the best opportunities. More