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

Chicago hotels, entertainment and free events

Deals into Fall
Source: Travel Discounters

Marvel at the pyramids, sail down the world's longest river, and save $580. Fly from major cities nationwide; includes hotels, tours and most meals.

Weekly departures, Sept. 15, 2014 - Nov. 30, 2015
Source: Apple Vacations

Be among the first to experience the newest 4-star, oceanfront resort during the grand opening of Dreams Sands Cancun Resort & Spa

Select Sept.-Oct. departures
Source: Lion World Travel

This opulent 5-star South Africa experience includes air, a treehouse stay, a wine tour, eight game drives, 18 meals and more

Select departures, Nov.-Dec. 2014; Jan.-March 2015
Source: Lion World Travel

View the big five up close on a 5-star trip complete with game drives, a helicopter ride, tours and more.

Select departures, Nov.-Dec. 2014; Jan.-May 2015
Source: Indus Travels

This vacation includes three of Latin America's most popular destinations at a cost-effective price.

Oct. 17; +$200 select November - April dates
Source: Savon Spa

Time Out Chicago likes the "of the moment" organic treatments at Savon Spa, which exudes a vibe that "channels old-world Paris."

July 30, 2014 - Oct. 30, 2014
Source: IPO Restaurant

New executive chef Fernando Coppola's first new menu at IPO in the Loop has been unveiled -- subscribers can get a first look at his brunch cuisine for 50% off.

Aug. 2, 2014 - Nov. 2, 2014
Source: The Great American Lobster Fest

The inaugural Great American Lobster Fest kicks off at Navy Pier during the Air & Water Show. Subscribers save 50% off on admission for two.

Aug. 16-17, 2014
Source: Cyrano's Farm Kitchen

Recently named one of the best French restaurants in the city (CBS Chicago), Cyrano's Farm Kitchen offers subscribers a three-course dinner for two.

July 25, 2014 - Oct. 25, 2014; closed Sunday-Monday
Source: The House Theatre of Chicago

Travelzoo subscribers can save 25% on tickets and get first access for popular dates to the "moving, family-friendly, richly imaginative" play (The Chicago Tribune).

July 24, 2014 - Aug. 9, 2014
Source: Steppenwolf Theatre Company

According to Time Out Chicago, "every comic beat lands just right" at Pulitzer Prize-winning playwright Bruce Norris' ("Clybourne Park") new comedy, "The Qualms."

Performances through Aug. 17
Source: Pars Cove

Pars Cove, an "intimate spot" (Metromix) in Lincoln Park that "offers a taste of the Middle East," invites subscribers for dinner and drinks for over 50% off.

July 24, 2014 - Oct. 24, 2014; not valid Saturdays
Source: Balance Spa & Fitness at Palmer House a Hilton Hotel

Frommer's says the AAA 4-Diamond Palmer House retains "a Gilded Age aura" in its "gorgeous lobby," which carries over to the luxurious Balance Spa.

July 18, 2014 - Dec. 31, 2014; Monday-Friday
Source: The Course at Aberdeen

"To experience a round of golf at Aberdeen is to enjoy golf at its finest," praises Michiana Golf. Subscribers can save more than 50% on a round this season.

Aug. 5, 2014 - Oct. 31, 2014
Source: Randolph Street Market

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

July 26, 2014 - Dec. 14, 2014; select weekends only
Source: Bolingbrook Golf Club

Named one of the top 30 public courses in America by Golf Digest readers in 2010, Bolingbrook offers subscribers up to 50% off a round through autumn.

July 18, 2014 - Nov. 16, 2014
Source: Bolingbrook Golf Club

Take a few swings at one of the Top 50 Driving Ranges in the Country (Golf Range Association of America 2013). Subscribers can drive for over 50% off.

July 18, 2014 - Nov. 16, 2014
Source: Weird Chicago Tours

Travelzoo subscribers can save more than 40% on admission to a Weird Chicago Tour now through the end of September.

Select tour dates through Sept. 30, 2014
Source: Live Nation

The bands will perform from their catalog of hits, including "If You Leave Me Now" (Chicago) and "Can't Fight This Feeling" (REO Speedwagon).

July 20, 2014
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Travis Kunz — Travel, Entertainment and Local Deal Expert
Travis Kunz
Deal Expert, Miami
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