70 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: Fabulous Fox Theatre

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

May 18-19
 
Source: TripMasters.com

Includes roundtrip airfare from the U.S. into Madrid and out of Barcelona, plus three nights in each city

Select dates May-August
 
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: Apple Vacations

Cabo awaits with this all-inclusive package that includes air, unlimited meals and drinks (including alcohol)and a $35 spa credit per adult

Select departures, May-June
 
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: Broadway In Chicago

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

May 10-12
 
Source: Broadway in Chicago

Choose from multiple performances, including evening and weekends.

May 10-22
 
Source: Cirque du Soleil

Save $10 on tickets to the family-friendly show

May 4-6 and 8
 
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: 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: City Winery

Visit City Winery in the West Loop, "a multifaceted amalgam of all things wine from drinking it to making it" (Zagat) and save 50% on brunch, lunch or dinner.

Through Aug. 15, 2016; Sunday-Thursday
90% (481 ratings)
 
Source: Paint Nite

Travelzoo members can flex their creative muscles during a two-hour Paint Nite event at bars around the country.

Through Dec. 31, 2016
 
Source: Uncorked Wine Festivals

Sample and savor wine tastings from more than 50 vendors at the inaugural Uncorked Wine Festival for 25% off.

May 7, 2016
 
Source: Pops for Champagne

"Those who worship the bubbly agree there's no substitute for this first-class purveyor of grand Champagne" (Zagat). Save over 40% on a visit to Pops.

Through Oct. 31, 2016; Sunday-Thursday
 
Source: Rittergut Wine Bar & Social Club

Save 35% on a night at Rittergut Wine Bar & Social Club, a riverside hideaway named one of the city's Best Wine Bars by CBS Chicago.

Through Sept. 8, 2016
91% (659 ratings)
 
Source: Hyde Park Brew Fest

The third annual Hyde Park Brew Fest takes place June 4-5, featuring top breweries from around the nation. Members can save over 35% on admission.

June 4-5, 2016; date specific event
 
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
97% (184 ratings)
 

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