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

Chicago hotels, entertainment and free events

Deals into Fall
Source: Hilton Chicago

Ideally located along famed Michigan Avenue, this 4-star hotel is the perfect home base for exploring Millennium Park and the museum campus.

Select dates Dec.-Feb.; Nov.-April also discounted
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 luxe dinner for two.

Jan. 2, 2015 - March 31, 2015; closed Sundays
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: 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.

Nov. 1, 2014 - April 30, 2015
Source: The Spa and Fitness Center at Four Seasons Hotel Chicago

The Spa and Fitness Center at Four Seasons Hotel Chicago "makes you feel right at home," raves Forbes Travel Guide, which ranks it 4 stars.

Jan. 5 - April 15, 2015; Mondays-Thursdays and Sundays after 3 p.m.
Source: Whisk Chicago

Inspired by noted carnivore Ron Swanson, Whisk "mixes burgers and pancakes in a way that would make the Parks and Rec character proud" (Chicago mag).

Oct. 6, 2014 - March 6, 2015; not valid Sundays
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.

Through March 31, 2015; 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: 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: 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: 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: G&O

From the same team behind the top-rated Aberdeen Tap, G&O offers an upscale bar menu and an "unpretentious craft cocktail list" (Chicago magazine).

Through Feb. 28, 2015, not valid Mondays
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.

Sept. 18, 2014 - Feb. 28, 2015
Source: Cook Au Vin

Get ready to knead, toss and mix your way to better baguettes and baked goods with a class from Cook au Vin, which earns 4.5 stars on Yelp.

Oct. 1, 2014 - April 1, 2015
Source: Elina Organics

Elina Organics offers what Chicago magazine calls Chicago's Best Facial, resulting in "soft, smooth skin [that's] radiant for days."

Sept. 4, 2014 - March 4, 2015; not valid Oct. 25-27
Source: International Museum of Surgical Science

"One of Chicago's most interesting and least famous museums, the International Museum of Surgical Science is a true gem" (USAToday's 10Best.com).

Through May 20, 2015; closed Mondays
Source: Brooklyn Boulders - Chicago

Subscribers save up to half off early access to the new Chicago location of Brooklyn Boulders, featuring climbing walls up to 50 feet high.

Nov. 18, 2014 - May 18, 2015
Source: Pazzo's @ 101

Dine with a view of the Lyric Opera building at Pazzo's @ 101, a 4-star OpenTable destination. Subscribers can save 35% on dinner.

Oct. 13, 2014 - Jan. 13, 2015; closed Sundays
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
Cheap Roundtrip Fares to Chicago from:
(Per person, including taxes and fees. Click a price to verify availability now.)
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

Hilary Solan — Travel, Entertainment and Local Deal Expert
Hilary Solan
Deal Expert, Chicago
Several hotel chains, including Hilton and Choice Hotels, offer discounts for active More