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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$2,214 to 🇭🇷 Zagreb, Croatia $99 to 🇺🇸 Atlanta, United States $690 to 🇨🇦 London, Canada See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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

$2,214

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May - May 2025
💰 $288
🇺🇸 Chicago, United States
🇭🇷 Zagreb, Croatia
Travel Between: 07 May 2025 To 14 May 2025

$99

*** - *** 2025
💰 $23 ⚡
🇺🇸 Chicago, United States
🇺🇸 Atlanta, United States
Travel Between: âš¡ Upgrade to premium plan to get access to travel dates and more.

$690

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May - May 2025
💰 $246
🇺🇸 Chicago, United States
🇨🇦 London, Canada
Travel Between: 28 May 2025 To 31 May 2025

$351

*** - *** 2025
💰 $933 ⚡
🇺🇸 Chicago, United States
🇨🇦 Toronto, Canada
Travel Between: âš¡ Upgrade to premium plan to get access to travel dates and more.

$1,266

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Jul - Jul 2025
💰 $631
🇺🇸 Chicago, United States
🇨🇦 Toronto, Canada
Travel Between: 08 July 2025 To 10 July 2025

$1,334

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Apr - Apr 2025
💰 $1,908
🇺🇸 Chicago, United States
🇮🇱 Tel Aviv, Israel
Travel Between: 13 April 2025 To 20 April 2025

$7,239

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Apr - Apr 2025
💰 $8,328
🇺🇸 Chicago, United States
🇮🇱 Tel Aviv, Israel
Travel Between: 11 April 2025 To 20 April 2025

$133

*** - *** 2025
💰 $322 ⚡
🇺🇸 Chicago, United States
🇺🇸 Tampa, United States
Travel Between: âš¡ Upgrade to premium plan to get access to travel dates and more.

$372

*** - *** 2024
💰 $186 ⚡
🇺🇸 Chicago, United States
🇺🇸 Honolulu, United States
Travel Between: âš¡ Upgrade to premium plan to get access to travel dates and more.

$222

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Aug - Oct 2023
💰 $111
🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico
Travel Between: Availability from August to October 2023

$366

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Aug - Oct 2023
💰 $183
🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia
Travel Between: Availability from August to October 2023

$298

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Aug - Oct 2023
💰 $149
🇺🇸 Chicago, United States
🇲🇽 Cozumel, Mexico
Travel Between: Availability from August to October 2023

$209

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Aug - Sep 2023
💰 $104
🇺🇸 Chicago, United States
🇲🇽 Cancun, Mexico
Travel Between: Availability from August to September 2023

$546

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Jan - Mar 2024
💰 $273
🇺🇸 Chicago, United States
🇲🇦 Casablanca, Morocco
Travel Between: Availability from January to March 2024

$177

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Aug - Oct 2023
💰 $88
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between: Availability from August to October 2023

$177

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Aug - Oct 2023
💰 $88
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between: Availability from August to October 2023

$348

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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: âš¡ 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