125 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Chicago

Chicago hotels, entertainment and free events

Deals into Fall
 
Source: The Westin Michigan Avenue

This 4-star hotel is close to the city's best shopping and dining.

Select dates Nov. 23 - Jan. 10
 
Source: Omni Chicago

Stretch out in a suite at a AAA 4-Diamond hotel on Chicago's famed Michigan Avenue.

Daily Oct. 26 - Jan. 31
 
Source: Wyndham Grand Chicago Riverfront

Fresh off a multi-million dollar redesign, receive an automatic room upgrade for stays into spring.

Dates through April 5, 2015
 
Source: Friendly Planet Travel

Depart from the U.S. on Emirates and continue the trip with 5-star hotels and a memorable itinerary including visits to the Taj Mahal and Burj Khalifa

February - April departures
 
Source: Travel Discounters

This tour includes an excursion to Abu Simbel, which is typically an additional cost for travellers.

Weekly departures through Nov. 30, 2015
 
Source: CheapCaribbean.com

Rejuvenate poolside as you spend four all-inclusive nights in Cabo

Select dates November-April
 
Source: CheapCaribbean.com

Trade falling temperatures for a beach chair on sugar-white sand lapped by turquoise waters. Perfect a sun-kissed glow with this Punta Cana vacation

Select departures November-April
 
Source: Lion World Travel

Sample the best of Cape Town and South Africa's exotic wildlife with a seven-night luxury vacation, including stays at a 5-star hotel and lodge.

Select dates January-December
 
Source: Vacation Express

Warm up this winter with four nights at a beachfront, all-inclusive Cancun resort including flights

Select January-April departures
 
Source: Major Airlines

Last chance to book holiday travel before prices rise.

Nov. 24 - Dec. 4
 
Source: Apple Vacations

While temps at home are dropping, heat things up in Cancun during peak season.

Select departures in January
 
Source: Sapori Trattoria

The "'down-home' cooking is 'guaranteed to delight'" (Zagat) at this Lincoln Park Italian destination, which earns an "excellent" (25) ranking for its cuisine.

Through April 30, 2015; Sunday-Thursday only
 
Source: Attila Glatz Concert Productions

"Salute to Vienna" is a live New Year's concert modeled after the traditional New Year's concert in Vienna. The lively performance is coming to Chicago, and subscribers can save 25% on tickets at Symphony Hall.

Sunday, Dec. 28 at 2:30 p.m.
 
Source: Via Veneto

This "cozy, charming" Italian restaurant with "helpful, friendly service" (Chicago Reader) offers subscribers savings of up to 50% off.

Oct. 30, 2014 - Feb. 25, 2015
 
Source: Chicago Philharmonic

Chicago Philharmonic performs three concerts this November at multiple venues including Jazz Showcase located downtown, City Winery in the West Loop and Nichols Hall in Evanston.

Nov. 3, 9, 16
 
Source: Harlem Globetrotters

The Harlem Globetrotters will look to show off top-notch basketball skills and keep one of the longest winning streaks in sports intact against the Washington Generals, making a return to the court for the first time in five years.

Dec. 28-29
 
Source: The Star on Grand

SFGate names The Star on Grand a "bright spot for pizza, cocktails" calling it "hip, yet still warm and neighborhoody."

Through April 28, 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.

Select weekends throughout 2014-15
 
Source: Roka Akor

Recommended by the 2013 Michelin Guide as a "sexy, sleek and energetic" lounge for "fashionable foodies," Roka Akor offers this unique lunch for two.

Nov. 3, 2014 - March 13, 2015
 
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Travelzoo Tips

Stephen Aviano — Travel, Entertainment and Local Deal Expert
Stephen Aviano
Deal Expert, New York
Take frame-worthy vacation shots with these tips from our photo pro. More