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)

$275

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Jan - Mar 2020 / Sep - Nov 2019
πŸ’° $225

Chicago, United States
Puerto Vallarta, Mexico

Travel Between: Varies by route. Generally September through November 2019 and January through March 2020, excluding Thanksgiving. Canada routes mostly available March 2020

$302

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Jan - Mar 2020 / Sep - Nov 2019
πŸ’° $198

Chicago, United States
Guatemala City, Guatemala

Travel Between: Varies by route. Generally September through November 2019 and January through March 2020, excluding Thanksgiving. Canada routes mostly available March 2020

$225

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Sep - Nov 2019 / Jan - Mar 2020
πŸ’° $275

Chicago, United States
Guadalajara, Mexico

Travel Between: Varies by route. Generally September through November 2019 and January through March 2020, excluding Thanksgiving. Canada routes mostly available March 2020

$314

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Jan - Mar 2020 / Sep - Nov 2019
πŸ’° $186

Chicago, United States
San Jose, Costa Rica

Travel Between: Varies by route. Generally September through November 2019 and January through March 2020, excluding Thanksgiving. Canada routes mostly available March 2020

$495

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Sep - Oct 2019 / Sep - Dec 2019
πŸ’° $355

Chicago, United States
Guangzhou, China

Travel Between: Varies greatly by route. Generally September through December 2019, some routes include Thanksgiving but all exclude Xmas/NYE. Many routes have availability September through October 2019 only

$502

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Sep - Oct 2019 / Sep - Dec 2019
πŸ’° $348

Chicago, United States
Shenzhen, China

Travel Between: Varies greatly by route. Generally September through December 2019, some routes include Thanksgiving but all exclude Xmas/NYE. Many routes have availability September through October 2019 only

$290

*** - *** 2019
πŸ’° $560 ⚑

Chicago, United States
Barcelona, Spain

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

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Aomori, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Fukuoka, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Hakodate, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Hiroshima, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Izumo, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Kitakyushu, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Nankoku, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Tokoname, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Niigata, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Saga, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$656

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $844

Chicago, United States
Chitose / Tomakomai, Japan

Travel Between: Varies by route. Generally September 2019 through April 2020, including cherry blossom season (late March through April 2020). Most routes include Thanksgiving but exclude Xmas/NYE

$563

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Sep - Apr 2020
πŸ’° $567

Chicago, United States
Tokyo, Japan

Travel Between: Β September 2019 to April 2020

$569

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Mar - Apr 2020 / Sep - Apr 2020
πŸ’° $831

Chicago, United States
Tokyo, Japan

Travel Between: Varies a bit by origin, but generally September 2019 through April 2020, including cherry blossom season (late March through April)

$364

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Sep - Nov 2019
πŸ’° $316

Chicago, United States
Kuala Lumpur, Malaysia

Travel Between: September to November 2019

$446

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Aug - Feb 2020
πŸ’° $554

Chicago, United States
Frankfurt-am-Main, Germany

Travel Between: Availability varies by origin. Play with Google flights between August 2019 and February 2020.

$584

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Sep - Apr 2020
πŸ’° $616

Chicago, United States
Tokyo, Japan

Travel Between: September 2019 through April 2020, including Thanksgiving but excluding Xmas/NYE

$618

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Aug - Apr 2020
πŸ’° $382

Chicago, United States
Hanoi, Vietnam

Travel Between: Varies slightly by route. Generally August 2019 through April 2020, including Thanksgiving but excluding Xmas/NYE
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