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.

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$372

*** - *** 2024
πŸ’° $186 ⚑

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡ΊπŸ‡Έ Honolulu, United States

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

$222

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Aug - Oct 2023
πŸ’° $111

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡²πŸ‡½ Cancun, Mexico

Travel Between: Availability from August to October 2023

$366

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Aug - Oct 2023
πŸ’° $183

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡¨πŸ‡΄ Bogota, Colombia

Travel Between: Availability from August to October 2023

$298

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Aug - Oct 2023
πŸ’° $149

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡²πŸ‡½ Cozumel, Mexico

Travel Between: Availability from August to October 2023

$209

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Aug - Sep 2023
πŸ’° $104

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡²πŸ‡½ Cancun, Mexico

Travel Between: Availability from August to September 2023

$546

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Jan - Mar 2024
πŸ’° $273

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡²πŸ‡¦ Casablanca, Morocco

Travel Between: Availability from January to March 2024

$177

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Aug - Oct 2023
πŸ’° $88

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡΅πŸ‡· San Juan, Puerto Rico

Travel Between: Availability from August to October 2023

$177

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Aug - Oct 2023
πŸ’° $88

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡΅πŸ‡· San Juan, Puerto Rico

Travel Between: Availability from August to October 2023

$348

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Sep - Oct 2023
πŸ’° $174

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡¨πŸ‡΄ Bogota, Colombia

Travel Between: Availability from September to October 2023

$329

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Aug - Oct 2023
πŸ’° $164

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡¨πŸ‡΄ Cartagena, Colombia

Travel Between: Availability from August to October 2023

$148

*** - *** 2023
πŸ’° $74 ⚑

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡ΊπŸ‡Έ 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
πŸ’° $101

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡΅πŸ‡· San Juan, Puerto Rico

Travel Between: Limited availability from October to November 2023

$354

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May - Feb 2024
πŸ’° $177

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡¨πŸ‡΄ Bogota, Colombia

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

$380

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Nov - Feb 2024
πŸ’° $190

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡«πŸ‡· Paris, France

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

$251

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Apr - May 2023
πŸ’° $125

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡²πŸ‡½ Cancun, Mexico

Travel Between: Availability from April to May 2023

$297

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Sep - Oct 2023
πŸ’° $148

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡²πŸ‡½ Mexico City, Mexico

Travel Between: Availability from September to October 2023

$148

*** - *** 2023
πŸ’° $74 ⚑

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡ΊπŸ‡Έ Seattle, United States

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

$106

*** - *** 2023
πŸ’° $53 ⚑

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡ΊπŸ‡Έ 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
πŸ’° $183

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡¨πŸ‡΄ Bogota, Colombia

Travel Between: Availability in May 2023

$182

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Oct - Nov 2023
πŸ’° $91

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡΅πŸ‡· San Juan, Puerto Rico

Travel Between: Availability from October to November 2023

$251

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Apr - Oct 2023
πŸ’° $125

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡²πŸ‡½ Cancun, Mexico

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

$293

View Deal
Aug - Nov 2023
πŸ’° $146

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡²πŸ‡½ Mexico City, Mexico

Travel Between: Availability from August to November 2023

$293

View Deal
Aug - Nov 2023
πŸ’° $146

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡²πŸ‡½ Mexico City, Mexico

Travel Between: Availability from August to November 2023

$294

View Deal
Sep - Nov 2023
πŸ’° $147

πŸ‡ΊπŸ‡Έ Chicago, United States
πŸ‡΅πŸ‡· Ponce, Puerto Rico

Travel Between: Availability from September to November 2023
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