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

Hotels, shows and attractions are discounted during a busy winter season

Deals into March
 
Source: Hotel Rush

Set in a prime location near the city’s best restaurants, iconic landmarks and top shopping.

Travel Jan. 4 - March 31
93% (15 ratings)
 
Source: Travelzoo

Nab sales at the city's top attractions while taking advantage of thinner crowds and shorter lines.

Through March
 
Source: Table, Donkey and Stick

Members can reserve a seat at the chef's counter at the Michelin-praised Table, Donkey and Stick for a five-course tasting menu and a drink for over 35% off.

Through April 30, 2015; blackout dates apply
 
Source: Apollo Theater

It's "musically dazzling from first beat to last" (Chicago Sun-Times).

Through March 29
 
Source: The Westin Michigan Avenue

Located just off Michigan Avenue, this 4-star hotel is close to Chicago's best shopping and dining.

Most dates through February; +$30 in March
 
Source: The Westin Michigan Avenue

Located just off Michigan Avenue, this 4-star hotel is close to Chicago's best shopping and dining

Most dates through February; +$50 in March
 
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.

Through 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.

Through April 15, 2015; Mondays-Thursdays and Sundays after 3 p.m.
 
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 members a luxe dinner for two.

Through March 31, 2015; closed Sundays
 
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: Level Two at the Hyatt Chicago Magnificent Mile

Start a weekend downtown trip off right -- members can save more than 40% on brunch with cocktails at Level Two, located at the Hyatt Chicago Magnificent Mile.

Through April 26, 2015; Saturday-Sunday only
 
Source: Pizzeria UNO

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

Through March 31, 2015; Tuesday-Saturday mornings
 
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).

Through March 6, 2015; not valid Sundays
 
Source: Cici Nails

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

Through Feb. 18, 2015
 
Source: Chuck's: A Kerry Simon Kitchen

With a new menu from celebrity chef Kerry Simon and his brother, executive chef Scott Simon, members can save 40% on a downtown dinner for two.

Through June 8, 2015
 
Source: ME SPA

Members can save over 55% on a range of massages and facials at seven ME SPA locations nationwide, great for a private winter escape or a relaxing gift.

Through Feb. 28, 2015
 
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.

Through Feb. 13, 2015
 
Source: Tiffani Kim Institute

Members can save nearly 55% on their choice of massage and facial at the Tiffani Kim Institute, a three-story urban River North spa escape.

Through June 26, 2015
 
Source: Meli Cafe

Praised on WTTW's "Check, Please!" for "a warm, welcoming atmosphere" where "attention is paid to every detail," Meli Cafe offers members up to 50% off.

Through March 23, 2015
 
Cheap Roundtrip Fares to Chicago from:
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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