9 deals from our Canadian site*
* Taxes and fees may be additional.
Source: Porter Airlines

Porter boasts a 4-star rating from Skytrax, leather seats, and free wine, beer, soda & snacks.

Through Sept. 3
 
Source: Porter Airlines

Save 60% with some of the lowest fares seen for travel into September.

Through Sept. 3
 
Source: Porter Airlines

Save 60% with some of the lowest fares seen for travel into September.

Through Sept. 3
 
Source: CityPASS

This offer saves on major attractions in any of these popular vacation spots.

Valid 9 days; redeem by Feb. 28, 2015
 
Source: trivago

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

Through spring
 
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: Porter Airlines

Snag a deal on summer travel aboard award-winning Porter Airlines, where in-flight benefits include free wine, beer, snacks and soft drinks.

Through Sept. 3
 
Travel into July
Major Airlines on Fly.com
 
 
53 deals from our U.S. site*
* Taxes and fees may be additional.

Deals are priced in U.S. dollars and are sourced by our U.S. Deal Experts. Airfare and air-inclusive vacation or cruise pricing includes taxes; hotel, entertainment, car rental, cruise and Local Deal prices do not include tax, and you may need to pay some tax directly to the provider.

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: 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: 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
 
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Greg Kunstler — Travel, Entertainment and Local Deal Expert
Greg Kunstler
Deal Expert, Toronto
Here are some I can no longer live without. More