Discover the Best Cheap Flight Deals from Chicago

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Latest cheap flight deals departing from Chicago.

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What is a premium fare? Airfare that is greater than 60% off the normal ticket price as well as airfare deals to top destinations such as Hawaii and Alaska.

Business Class & Non-stop Flights
Departure Airport(s)
Destination Airport(s)


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Jan - Mar 2020 / Aug - Nov 2019
💰 $100

Chicago, United States
San Juan, Puerto Rico

Travel Between: Varies greatly by origin. Generally August through November 2019 and January through March 2020, all excluding Thanksgiving


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Aug - Sep 2019
💰 $94

Chicago, United States
Dallas-Fort Worth, United States

Travel Between: August to September 2019


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Apr - Mar 2020
💰 $285

Chicago, United States
Montreal, Canada

Travel Between: Generally end of April 2019 through March 2020, most routes include Thanksgiving and some routes include Xmas/NYE for $50 more


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Aug - Oct 2019
💰 $121

Chicago, United States
New Orleans, United States

Travel Between: August to October 2019


*** - *** 2019
💰 $604

Chicago, United States
Lima, Peru

Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.


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Sep - Oct 2019 / Apr - Feb 2020
💰 $279

Chicago, United States
Calgary, Canada

Travel Between: Scattered availability April 2019 through February 2020. Most availability September through October 2019. Some routes have more limited availability. Only some routes have peak summer and Thanksgiving availability, while none have Xmas/NYE


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Sep - May 2019
💰 $238

Chicago, United States
San Juan, Puerto Rico

Travel Between: Varies by origin. Generally September 2018 through May 2019, including some Thanksgiving but excluding Xmas/NYE


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Jul - Apr 2019
💰 $217

Chicago, United States
Puerto Vallarta, Mexico

Travel Between: Varies by origin. Generally late July 2018 through April 2019, some routes including Thanksgiving, some including Xmas if you go for 2 week+ periods, and all excluding NYE.