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Discover the Best Cheap Flight Deals from Chicago

We collect cheap flight deals from around the web, and provide our subscribers a more personalized flight deals feed, straight to their inbox. Join over 100,000 subscribers.

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Recent deals from Chicago:

$496 to 🇵🇹 Lisbon, Portugal $191 to 🇵🇷 San Juan, Puerto Rico $876 to 🇵🇭 Manila, Philippines See more deals from Chicago

Showing flight deals from Chicago

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.

Flights Options
Departure Airport(s)
Destination Airport(s)
Departure Country Pro Only
Destination Country Pro Only
Flights Under Pro Only

$496

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Dec - Dec 2024
💰 $248
🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal
Travel Between:

$191

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Apr - Apr 2025
💰 $95
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$876

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Mar - Mar 2025
💰 $438
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$405

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Mar - Mar 2025
💰 $202
🇺🇸 Chicago, United States
🇳🇴 Stavanger, Norway
Travel Between:

$369

*** - *** 2025
💰 $184 ⚡
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$405

View Deal
Mar - Mar 2025
💰 $202
🇺🇸 Chicago, United States
🇳🇴 Bergen, Norway
Travel Between:

$836

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Jan - Jan 2025
💰 $418
🇺🇸 Chicago, United States
🇹🇼 Kaohsiung City, Taiwan
Travel Between:

$870

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Feb - Feb 2025
💰 $435
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$496

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Nov - Nov 2024
💰 $248
🇺🇸 Chicago, United States
🇪🇸 Barcelona, Spain
Travel Between:

$832

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Feb - Feb 2025
💰 $416
🇺🇸 Chicago, United States
🇦🇺 Brisbane, Australia
Travel Between:

$180

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Nov - Nov 2024
💰 $90
🇺🇸 Chicago, United States
🇵🇷 Aguadilla, Puerto Rico
Travel Between:

$517

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Nov - Nov 2024
💰 $258
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$421

View Deal
Nov - Nov 2024
💰 $210
🇺🇸 Chicago, United States
🇪🇸 Madrid, Spain
Travel Between:

$474

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Nov - Nov 2024
💰 $237
🇺🇸 Chicago, United States
🇵🇹 Porto, Portugal
Travel Between:

$823

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Oct - Oct 2024
💰 $411
🇺🇸 Chicago, United States
🇹🇼 Taipei, Taiwan
Travel Between:

$810

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Oct - Oct 2024
💰 $405
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$874

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Oct - Oct 2024
💰 $437
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$477

View Deal
Nov - Nov 2024
💰 $238
🇺🇸 Chicago, United States
🇫🇷 Nice, France
Travel Between:

$341

*** - *** 2024
💰 $170 ⚡
🇺🇸 Chicago, United States
🇺🇸 Kahului, United States
Travel Between: ⚡ Upgrade to premium plan to get access to travel dates and more.

$398

View Deal
Nov - Nov 2024
💰 $199
🇺🇸 Chicago, United States
🇩🇰 Copenhagen, Denmark
Travel Between:

$399

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💰 $199
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between:

$403

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Mar - Mar 2025
💰 $201
🇺🇸 Chicago, United States
🇱🇺 Luxembourg, Luxembourg
Travel Between:

$399

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Jan - Jan 2025
💰 $199
🇺🇸 Chicago, United States
🇵🇱 Warsaw, Poland
Travel Between:

$455

View Deal
Nov - Nov 2024
💰 $227
🇺🇸 Chicago, United States
🇪🇸 Barcelona, Spain
Travel Between: