102 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Live Nation

Accompanied by a 14-piece band, the concert will feature material from the singer’s iconic career, and her new critically acclaimed album

May 22-June 29
 
Source: CheapCaribbean.com

Make a break for Cancun and spend four all-inclusive nights at a newly renovated beachfront resort

Select departures June-November
 
Source: Travel Discounters

Take advantage of the wide travel window to have the chance to see Cairo at your leisure with this partially-guided tour

Weekly departures through November 2016
 
Source: Sinorama Holidays

This early-bird special offers a comprehensive itinerary, Yangtze cruise and set of upscale hotels, plus an English-speaking guide

Select departures March-December 2016
 
Source: Lion World Travel

Stay at 5-star award-winning hotels, with included perks like a massage and helicopter ride.

Select September-March departures
 
Source: Broadway In Chicago

"Once" -- the Broadway musical that won eight Tonys (including Best Musical), four Drama Desk Awards and a Grammy -- is coming to Chicago next week. This deal saves up to 45% on tickets to the rarely discounted touring show.

June 2 & 3
 
Source: Institute of Skin and Body

Travelzoo members can save up to 60% on a relaxing trip to the top-rated Institute of Skin and Body on the city's Northwest Side.

Through Sept. 30, 2015
 
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: Wingout Chicago

Head to Old Town for beers, blues music and all-you-can-eat wings from top restaurants around Chicago. Members can attend Wingout for 35% off.

June 6-7, 2015
 
Source: International Museum of Surgical Science

"One of Chicago's most interesting and least famous museums, the International Museum of Surgical Science is a true gem" (USAToday's 10Best.com).

Through Sept. 30, 2015; closed Mondays
 
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.

May 23, 2015 - Sept. 5, 2015; trips run Friday-Sunday
 
Source: Blue Man Group

Blue Man Group at Briar Street Theatre in Chicago is now offering Travelzoo members an exclusive deal that saves $20 on all performances May 25 - Oct. 3.

Shows May 25 - Oct. 3
 
Source: Wrigley View Rooftop

Six-time Grammy winner and Rock and Roll Hall of Famer Billy Joel is returning to Wrigley Field this summer; catch the concert from an all-inclusive rooftop with a view of the stage.

Thursday, Aug. 27 at 8 p.m.
 
Source: mEAT - Streeterville

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

May 18, 2015 - Nov. 18, 2015
 
Source: 'Defending the Caveman'

"Defending the Caveman" has been called "outrageously funny and surprisingly sweet" by the Chicago Sun-Times. With this offer, tickets to the critically acclaimed show are 50% off for Travelzoo members.

Through 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: 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: Chicago Water Sport Rentals

Get out on Lake Michigan this summer. Travelzoo members can paddle over the waves or roar across the water on a Jet Ski for 50% off with this offer.

Through Oct. 30, 2015
 
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: 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
 
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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