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

Chicago hotels, entertainment and free events

Deals into Fall
 
Source: Hotel Lincoln

Views of Lake Michigan await guests at a classic Chicago hotel

Dates through March 31
95% (66 ratings)
 
Source: Apple Vacations

This beachfront winter escape includes unlimited meals and drinks and a stay in a junior suite

Select departures in January
 
Source: dana hotel and spa

Three blocks from the Magnificent Mile, book a stay at this lively hotel and receive a $10 voucher for breakfast.

Through April 6, 2015
95% (40 ratings)
 
Source: Travel Discounters

This trip includes excursions that often cost extra with other tour operators.

Weekly departures through December 2015
 
Source: CheapCaribbean.com

Escape the winter chill at this resort, which Fodor's calls an "ideal choice" for those "looking for an all-inclusive offering with high standards"

Select departures January-June
 
Source: Vacation Express

Be a trendsetter at a brand-new adults-only resort on Uvero Alto beach

Select March-May­ departures
 
Source: American Airlines

With American Airlines' wide network, fares are discounted from more than 100 cities nationwide.

Select dates Dec. 23 - June 4
 
Source: Tocco

Neapolitan pizza fans, take note -- "no one should doubt that serious pizzas emerge" from the woodburning ovens at Wicker Park's Tocco (Chicago Reader).

Jan. 6, 2015 - April 1, 2015; Tuesday-Thursday only
 
Source: Celestial Sails

Reserve a spot on a Lake Michigan cruise or watch the fireworks with Celestial Sails this summer. Save 60% on a semi-private trip.

April 15, 2015 - Oct. 15, 2015
 
Source: Grapes to Bottles

Sample dozens of different wines at your choice of events at the Dana Hotel's Freestyle Food + Drink, hosted by the Grapes to Bottles team.

Jan. 17, 2015 and Jan. 31, 2015
 
Source: Ivy Boutique Hotel

For $109 per night, stay in an upgraded suite at the 4.5-star Ivy Boutique Hotel, one block from Magnificent Mile, with a deal that saves 50%.

Travel through March 31, 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: deca Restaurant + Bar at the Ritz-Carlton Chicago

Members can savor three courses each at the Ritz-Carlton's deca Restaurant + Bar, ranked "Very Good to Excellent" (23) across the board by Zagat.

Jan. 2, 2015 - April 30, 2015
 
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 Jan. 31
 
Source: iO Chicago Theater

With former cast members like Tina Fey, Amy Poehler and Seth Meyers, iO Chicago features tomorrow's famous comedians performing today.

Dec. 16, 2014 - March 31, 2015
 
Source: Trattoria Isabella

Metromix likes the "hearty portions" of "must try" appetizers and says "it's tough to choose" between Trattoria Isabella's Sicilian-focused entrees.

Through Jan. 13, 2015; Sunday-Thursday only
 
Source: VALEO at the JW Marriott Chicago

Spend a night at the "luxurious and majestic" JW Marriott Chicago (The New York Times) with a $100 credit to one of the city's best spas (Chicago magazine).

Travel daily through March 29, 2015 (blackout dates apply)
 
Source: Level Two at the Hyatt Chicago Magnificent Mile

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

Dec. 13, 2014 - April 26, 2015; Saturday-Sunday only
 
Source: 'Million Dollar Quartet'

Music from Elvis Presley, Johnny Cash, Jerry Lee Lewis and Carl Perkins comes to life in "Million Dollar Quartet," now a staple at Chicago's Apollo Theater.

Dec. 8, 2014 - Dec. 20, 2014
 
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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