60 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

Oct. 22 - Feb. 28
 
Source: CheapOair

Book by Wednesday and fly to/from San Diego, Vegas, Los Angeles, Seattle, Jamaica, Iceland and more

Travel Oct. 7 - Dec. 17
 
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: 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: 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: 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: IPO Restaurant

New executive chef Fernando Coppola's first 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: CURRENT at W Chicago Lakeshore

CURRENT has only been open since May, but Crain's is already praising the "sophisticated menu" where "everything is impressively on target."

July 15, 2014 - Oct. 15, 2014
 
Source: Pizzeria UNO

Pizzeria UNO is where Chicago's iconic deep-dish pizza was created over 70 years ago. With this exclusive offer, subscribers can learn to craft their own.

Aug. 20, 2014 - Dec. 30, 2014; Tuesday-Saturday mornings
 
Source: Cici Nails

Harper's Bazaar says autumn nail trends include deep reds, grays and metallics. Subscribers can prepare their digits for fall and save half off.

Aug. 19, 2014 - Feb. 18, 2015
 
Source: Rivers

Located along the Chicago River, the appropriately named Rivers is "elegant" with "sleek contemporary appeal" (Metromix).

Aug. 20, 2014 - Oct. 10, 2014
 
Source: On The Bun

On The Bun features burgers made from prime and Kobe-style steak, served on pretzel rolls or even waffles. Subscribers can visit and save 50%.

May 1, 2014 - Nov. 1, 2014
 
Source: Hana Lounge at Westin Chicago River North

This "calm, soothingly lit refuge" (Examiner.com) in River North opens its doors to Travelzoo subscribers for drinks and apps for more than 50% off.

Aug. 12, 2014 - Nov. 12, 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: Nia

This "comfortable tapas spot" in the West Loop offers "a laid back vibe" (Metromix). Subscribers can save over 40% on a selection of tapas and drinks.

Aug. 11, 2014 - Nov. 30, 2014
 
Source: The Garage & The Salsa Truck

Savor gourmet tacos and a rotating menu from Chicago's food truck community for 40% off at the Garage, home of the Salsa Truck.

Sept. 15, 2014 - Jan. 15, 2015
 
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
 
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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