82 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: InterTrips.com

Featuring the lowest price we've seen in a decade, this Thailand trip includes international air, a 4-star hotel stay, transfers, city tour and taxes

Select departures in November; January-March 2017
 
Source: Fabulous Fox Theatre

The Chicago Tribune says it's "the most exciting musical Broadway has seen in years."

May 18-19
 
Source: CruCon Cruise Outlet

This deal features some of the lowest prices we’ve seen for Caribbean sailings all year as part of a buy one, get one 60% off promotion.

Select 2016-2017 dates
 
Source: Lion World Travel

This luxe Cape Town and safari adventure includes flights, top-rated accommodations, fine cuisine, tours by land and air, game drives and more.

Select dates Sept. 19 - Dec. 8
 
Source: Vacation Express

At these prices, we're surprised to see a 4-star all-inclusive Omni with sushi bars and waterfalls.

Select dates May-October
 
Source: Vacation Express

This budget-friendly resort sits on prime real estate in award-winning Bavaro Beach.

Select dates May-October
 
Source: TripMasters.com

Includes roundtrip airfare from the U.S. into Athens and out of Santorini

Select dates May-August
 
Source: Frontier Airlines on Fly.com

June - August
 
Source: Broadway In Chicago

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

May 10-12
 
Source: The National Theatre

All midweek performances are included in this offer, plus two Friday and two Sunday night shows.

Select dates May 3-15
 
Source: The Philadelphia Orchestra

The concert includes pieces by famed conductor and composer John Williams and Beethoven's No. 7.

May 5-7
 
Source: Straz Center for the Performing Arts

The New York Post called the musical "too good to be true."

June 1-3 & 5
 
Source: Virgin America

Fly across the country on the 'Best U.S. Airline' (Conde Nast Traveler Readers' Choice Awards)

Sept. 7 - Nov. 16
 
Source: Travel Discounters

The Semiramis cruise ship offers 66 cabins, panoramic windows, a sun deck and nightly entertainment.

Depart Wednesdays Sept. 11 - Nov. 30
 
Source: Oceanique

Evanston's Oceanique is a "fine-dining standby" with "haute cuisine moves" at a "perennially popular" spot (Chicago magazine).

Through Sept. 30, 2016
87% (214 ratings)
 
Source: Spirit Cruises

Save 50% on any dinner cruise through May only on Spirit of Chicago or Odyssey Chicago, which earns a 4-star rating from TripAdvisor users.

May 1-31, 2016
98% (43 ratings)
 
Source: Straz Center for the Performing Arts

The Chicago Tribune declared Tony Award winner "Jersey Boys" to be "the most exciting musical Broadway has seen in years." Travelzoo members can save up to 45% on performances when the show returns to Tampa.

June 1-3 & 5
 
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.
 

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