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.

Flights Options

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

$348

View Deal
Sep - Oct 2023
💰 $174

🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia

Travel Between: Availability from September to October 2023

$329

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Aug - Oct 2023
💰 $164

🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia

Travel Between: Availability from August to October 2023

$148

*** - *** 2023
💰 $74

🇺🇸 Chicago, United States
🇺🇸 Seattle, United States

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

$202

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Oct - Nov 2023
💰 $101

🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico

Travel Between: Limited availability from October to November 2023

$354

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May - Feb 2024
💰 $177

🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia

Travel Between: Availability from May 2023 to February 2024 (excluding Christmas/New Year)

$380

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Nov - Feb 2024
💰 $190

🇺🇸 Chicago, United States
🇫🇷 Paris, France

Travel Between: Limited availability from November 2023 to February 2024 (excluding Christmas/New Year)

$251

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Apr - May 2023
💰 $125

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between: Availability from April to May 2023

$297

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Sep - Oct 2023
💰 $148

🇺🇸 Chicago, United States
🇲🇽 Mexico City, Mexico

Travel Between: Availability from September to October 2023

$148

*** - *** 2023
💰 $74

🇺🇸 Chicago, United States
🇺🇸 Seattle, United States

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

$106

*** - *** 2023
💰 $53

🇺🇸 Chicago, United States
🇺🇸 New York, United States

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

$366

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May - May 2023
💰 $183

🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia

Travel Between: Availability in May 2023

$182

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Oct - Nov 2023
💰 $91

🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico

Travel Between: Availability from October to November 2023

$251

View Deal
Apr - Oct 2023
💰 $125

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between: Availability from April to October 2023 (excluding summer)

$293

View Deal
Aug - Nov 2023
💰 $146

🇺🇸 Chicago, United States
🇲🇽 Mexico City, Mexico

Travel Between: Availability from August to November 2023

$293

View Deal
Aug - Nov 2023
💰 $146

🇺🇸 Chicago, United States
🇲🇽 Mexico City, Mexico

Travel Between: Availability from August to November 2023

$294

View Deal
Sep - Nov 2023
💰 $147

🇺🇸 Chicago, United States
🇵🇷 Ponce, Puerto Rico

Travel Between: Availability from September to November 2023

$294

View Deal
Sep - Nov 2023
💰 $147

🇺🇸 Chicago, United States
🇵🇷 Ponce, Puerto Rico

Travel Between: Availability from September to November 2023

$248

*** - *** 2023
💰 $124

🇺🇸 Chicago, United States
🇺🇸 Anchorage, United States

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

$248

*** - *** 2023
💰 $124

🇺🇸 Chicago, United States
🇺🇸 Anchorage, United States

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

$547

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Jan - Jan 2024
💰 $273

🇺🇸 Chicago, United States
🇲🇦 Casablanca, Morocco

Travel Between: Availability in January 2024

$349

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Apr - May 2023
💰 $174

🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia

Travel Between: Limited availability from April to May 2023

$337

View Deal
Nov - Nov 2023
💰 $168

🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland

Travel Between: Availability in November 2023

$273

View Deal
Apr - May 2023
💰 $136

🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico

Travel Between: Availability from April to May 2023

$387

View Deal
Oct - Nov 2023
💰 $193

🇺🇸 Chicago, United States
🇨🇴 Barranquilla, Colombia

Travel Between: Limited availability from October to November 2023
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