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

Chicago hotels, entertainment and free events

Deals into Fall
 
Source: Virgin America

Book a getaway on this top-rated airline

Aug. 19 - Nov. 19
 
Source: Sheraton Chicago Hotel & Towers

Take in top city sights and skyline views from a 4-star Chicago hotel.

Select dates through Oct. 4
 
Source: American Airlines

Fly to cities nationwide including New York, Las Vegas, Austin, Miami, Los Angeles, Chicago and more

Select dates Aug. 25 - Dec. 17
 
Source: Featured Destination: Puerto Rico

Escape to the Caribbean this summer with increased airlift, including Southwest and United flights

Through August
 
Source: The Westin Chicago River North

Walk to the theater, trendy shops and top restaurants from this 4-Diamond hotel.

Select dates through Sept. 2
 
Source: Seadog Cruises

Take a thrilling trip underneath exploding summer fireworks this season with the top-rated Seadog Cruises. Subscribers save 40% on a Wednesday excursion.

May 28, 2014 - Aug. 27, 2014; specific dates only
 
Source: Medieval Times

Dine like royalty on a four-course feast and save up to 40% with this offer for the jousting and sword-fighting show at Medieval Times in Schaumburg.

Valid for use through Sept. 2
 
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 subscribers a luxurious dinner for two.

June 2, 2014 - Aug. 30, 2014; closed Sundays
 
Source: Rittergut Wine Bar & Social Club

Save over 50% on wine flights paired with gourmet charcuterie and cheese at this riverside hideaway, named one of the city's Best Wine Bars by CBS Chicago.

April 14, 2014 - Sept. 4, 2014; closed Sundays; not available on Saturdays after May 24
 
Source: Tortoise Club

When Keene Addington opened Tortoise Club, a classic supper club in River North, Crain's called it an "instant classic," adding "Mr. Addington has a winner."

June 19, 2014 - Sept. 19, 2014
 
Source: Old Fifth

RedEye says Old Fifth, featuring a "dynamic duo" of pizza and whiskey, "should be at the top of your list" for pies made with a "sweeter sauce with a bit of spice."

June 19, 2014 - Sept. 19, 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: Brando's Speakeasy

"Brando’s Speakeasy is anything but what it seems," says Time Out Chicago, praising the vintage decor mixed with "modern flair."

May 29, 2014 - Oct. 29, 2014
 
Source: Chicago's Finest Tours

"The information provided was stellar!" "I can't say enough good things about the tour." Subscribers love Chicago's Finest; reserve a tour this summer for 50% off.

June 1, 2014 - Oct. 31, 2014
 
Source: Chicago Sailboat Charters

Sailing the waters of Lake Michigan for more than a decade, Chicago Sailboat Charters earns a perfect 5 stars on Yelp for their first-class sailboat trips.

May 16, 2014 - Sept. 14, 2014
 
Source: Encore Chicago

A luxe lounge in the Loop, Encore is a "prime spot for a bite to eat at noontime" (Centerstage). Two can sit down to lunch for less than $10 per person.

March 27, 2014 - Sept. 26, 2014; Monday-Friday only
 
Source: Mission Hills Golf Course

After five decades as a private course, Mission Hills opened its doors to public play this year. Subscribers can save on a round with cart and lunch.

July 15, 2014 - Oct. 15, 2014
 
Source: Oxygen Spa Studio

Oxygen Spa Studio has quickly become a popular destination for massage services, earning 4.5 stars from nearly a hundred Yelp reviewers.

June 9, 2014 - Nov. 9, 2014
 
Source: Usagi Ya Sushi

The 2013 Michelin Guide says that the Usagi Ya menu "shines with its unorthodox combinations." Subscribers save more than 50% on this four-course dinner.

March 6 - Sept. 6, 2014
 
Cheap Roundtrip Fares to Chicago from:
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Travis Kunz — Travel, Entertainment and Local Deal Expert
Travis Kunz
Deal Expert, Miami
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