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

Chicago hotels, entertainment and free events

Deals into Fall
 
Source: Inn of Chicago

Unpack at one of the best locations in Chicago -- one block from famed Michigan Avenue -- with stay dates available through fall and winter.

Dec. 7 - March 12; fall dates also available
88% (9 Ratings)
 
Source: Browntrout

Discover "surprising, inspiring" cuisine that Zagat rates as Excellent (24) at Browntrout. Save on a selection of small plates including a $50 wine credit.

Sept. 18, 2014 - Nov. 30, 2014
 
Source: Virgin America

Book a getaway on this top-rated airline

Oct. 11 - March 4
 
Source: Sheraton Chicago Hotel & Towers

Stay over the holidays at this hotel near Navy Pier

Select dates through December
 
Source: The Westin Michigan Avenue

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

Select dates through Nov. 22
 
Source: The Westin Chicago River North

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

Select dates in November-December
 
Source: Naples Rib Company and Newport Rib Company

Named one of OpenTable's top U.S. barbecue spots, Naples Rib Company and sister eatery Newport Rib Company invite Travelzoo users to dine for half off.

July 30, 2014 - Nov. 26, 2014
 
Source: Swoon Dessert Bar

San Diego Reader calls the inventive confections at Swoon Dessert Bar "brilliant," praising the "marvelous level of talent on display."

April 30, 2014 - Oct. 29, 2014; closed Mondays and Tuesdays
 
Source: Odyssey Cruises

Set sail on the Odyssey, "the largest and most luxurious of the boats that dock along ... Navy Pier" (CBS Chicago), and save up to 45% on a dinner cruise.

July 30, 2014 - Nov. 30, 2014
 
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: 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: 'Defending the Caveman'

Save up to 70% on tickets to see "Defending the Caveman," a critically acclaimed show full of comedic observations on the gender gap.

Shows through Dec. 31, 2014
 
Source: Madame Tussauds Washington D.C.

Brush elbows with the Founding Fathers and A-list celebrities like George Clooney and Angelina Jolie with 40%-off tickets to Madame Tussauds.

Aug. 21, 2014 - March 31, 2015
 
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 fall for 50% off.

June 1, 2014 - Oct. 31, 2014
 
Source: Kohl Children's Museum

Kohl Children's Museum "raises 'let's pretend' to an art form" (Metromix); in 2011 Parents Magazine named it one of the best children's museums in America.

Aug. 18, 2014 - Nov. 21, 2014
 
Source: Expertly Crafted Wellness

Save 50% on your choice of massage at Expertly Crafted Wellness, which earns a 94% approval rating from recent Travelzoo guests.

May 27, 2014 - Oct. 30, 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: 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: Bourbon DC - Adams Morgan

Sip on cocktails rated among the best in D.C. at Bourbon in Adams Morgan, where you can "kick back" on the "warm, pleasant" outdoor patio (DCist).

July 15, 2014 - Jan. 31, 2015
 
Cheap Roundtrip Fares to Chicago from:
(Per person, including taxes and fees. Click a price to verify availability now.)
fly.com
more cities
close close
Don’t see your city listed above? Search for flights to Chicago:

Still looking for your flight?
Try Fly.com, a new airfare search engine from





Compare Hotel Rates

Travelzoo Tips

Chris Vassil — Travel, Entertainment and Local Deal Expert
Chris Vassil
Deal Expert, Chicago
Going as a grown-up is just as fun, if not more so, than going at age 6. Here's why. More