56 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Trump International Hotel & Tower Chicago

Luxuriate at a downtown Chicago hotel with show-stopping views and a long list of awards, including Travel + Leisure’s World’s Best.

Select dates through July 8
 
Source: Hotel Lincoln

Take on Chicago like a local at a boutique 4-star hotel, located in the city's posh Lincoln Park neighborhood.

Most Sundays-Thursdays through Aug. 27
 
Source: Bottlenotes

Swirl & sip wines from California, Spain, France, Italy, New Zealand and Brazil during "Around the World in 80 Sips" at the Museum of Contemporary Art

Friday, May 9
 
Source: Virgin America

Fly in Main Cabin Select and get unlimited food, drinks and entertainment; extra legroom and a complimentary checked bag.

May 8 - June 11; Sep. 3 - Nov. 19
 
Source: American Airlines

This nationwide sale features fares to/from major US cities including NYC, Miami, Los Angeles and Chicago

Travel through June 7, book by April 24
 
Source: trivago

Find the lowest prices at hotels across the city, from the Loop to Streeterville and Lincoln Park

Through spring
 
Source: The Westin Michigan Avenue

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.

Select dates through July 8
 
Source: The Westin Chicago River North

Check in to a AAA 4-Diamond hotel with a top location and sweeping views of the Chicago river.

Select dates through Sept. 1
 
Source: Sheraton Chicago Hotel & Towers

Take in top city sights and skyline views from a 4-star Chicago hotel.

Select dates through Oct. 4
 
Source: Rittergut Wine Bar & Social Club

Save over 50% on wine flights paired with gourmet charcuterie and cheese at this riverside hideaway, named one of the city's Best Wine Bars by CBS Chicago.

April 14, 2014 - Sept. 4, 2014; closed Sundays; not available on Saturdays after May 24
 
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 grand lobby, which carries over to the luxurious Balance Spa.

Feb. 18, 2014 - June 13, 2014; valid Monday - Friday only
 
Source: Pizzeria del Mercato

Praising the "crispy crusts and housemade cheeses," Chicago Magazine calls Pizzeria del Mercato "a welcome newcomer to Chicago's pizza scene."

March 21, 2014 - June 21, 2014
 
Source: Tall Ship Red Witch

CBS Chicago calls a trip on the Red Witch one of the best in Chicago. Plan ahead for summer and book a Skyline Sail or Fireworks Sail for 50% off.

May 15, 2014 - July 31, 2014
 
Source: Wateriders Kayak Tours & Rentals

The Sun-Times, Washington Post and Lonely Planet all recommend the guided river tours from Wateriders. Subscribers save 50% off tours for two.

May 1, 2014 - Sept. 28, 2014
 
Source: Studio Within Salon/Spa

Save 50% on an hourlong massage and facial with a blowout at a top-rated Lakeview salon and spa, which earns 4 stars from more than 100 Yelpers.

Jan. 27, 2014 - July 27, 2014
 
Source: Chicago Sailboat Charters

Sailing the waters of Lake Michigan for more than a decade, Chicago Sailboat Charters earns a perfect 5 stars on Yelp for their first-class sailboat trips.

May 16, 2014 - Sept. 14, 2014
 
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.

March 6 - Sept. 6, 2014
 
Source: Theory

Travelzoo subscribers can save up to 59% off lunch or brunch at this award-winning "modern sports-focused lounge" (Metromix) in River North.

April 15, 2014 - July 15, 2014; brunch served Saturday-Sunday, lunch Monday-Friday
 
Source: Encore Chicago

A luxe lounge in the Loop, Encore is a "prime spot for a bite to eat at noontime" (Centerstage). Two can sit down to lunch for less than $10 per person.

March 27, 2014 - Sept. 26, 2014; Monday-Friday only
 
Source: Chicago's Home of Chicken & Waffles

Featuring over a dozen different chicken/waffle options, Chicago's Home of Chicken and Waffles offers dinner for two with drinks for over 45% off.

March 18, 2014 - June 18, 2014
 
Cheap Roundtrip Fares to Chicago from:
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Andrew Young — Travel, Entertainment and Local Deal Expert
Andrew Young
Deal Expert, New York
Summer is coming. Our thoughts turn to beaches, grilling meats and summer vacation. More