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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$567 to 🇬🇷 Athens, Greece $560 to 🇪🇸 Barcelona, Spain $556 to 🇪🇸 Madrid, Spain See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$567

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Nov - Nov 2026
💰 $283
🇺🇸 Chicago, United States
🇬🇷 Athens, Greece
Travel Between:

$560

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Oct - Oct 2026
💰 $280
🇺🇸 Chicago, United States
🇪🇸 Barcelona, Spain
Travel Between:

$556

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Nov - Nov 2026
💰 $278
🇺🇸 Chicago, United States
🇪🇸 Madrid, Spain
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$509

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Nov - Nov 2026
💰 $254
🇺🇸 Chicago, United States
🇮🇹 Rome, Italy
Travel Between:

$217

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Nov - Nov 2026
💰 $108
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
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$518

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Jan - Jan 2027
💰 $259
🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland
Travel Between:

$398

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Oct - Oct 2026
💰 $199
🇺🇸 Chicago, United States
🇮🇸 Reykjavik, Iceland
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$494

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💰 $247
🇺🇸 Chicago, United States
🇺🇸 Kahului, United States
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$888

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Nov - Nov 2027
💰 $444
🇺🇸 Chicago, United States
🇳🇿 Auckland, New Zealand
Travel Between:

$891

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Nov - Nov 2026
💰 $445
🇺🇸 Chicago, United States
🇲🇾 Kota Kinabalu, Malaysia
Travel Between:

$891

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Jan - Jan 2027
💰 $445
🇺🇸 Chicago, United States
🇲🇾 Kota Kinabalu, Malaysia
Travel Between:

$889

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Nov - Nov 2026
💰 $444
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$911

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💰 $455
🇺🇸 Chicago, United States
🇺🇿 Tashkent, Uzbekistan
Travel Between:

$498

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Apr - Apr 2027
💰 $249
🇺🇸 Chicago, United States
🇳🇴 Kjevik, Norway
Travel Between:

$819

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Nov - Nov 2026
💰 $409
🇺🇸 Chicago, United States
🇹🇭 Chiang Mai, Thailand
Travel Between:

$819

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Nov - Nov 2026
💰 $409
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$499

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Feb - Feb 2027
💰 $249
🇺🇸 Chicago, United States
🇳🇴 Trondheim, Norway
Travel Between:

$895

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Sep - Sep 2026
💰 $447
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$498

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Feb - Feb 2027
💰 $249
🇺🇸 Chicago, United States
🇳🇴 Bergen, Norway
Travel Between:

$304

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Nov - Nov 2026
💰 $152
🇺🇸 Chicago, United States
🇵🇷 Ponce, Puerto Rico
Travel Between:

$829

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Sep - Sep 2026
💰 $414
🇺🇸 Chicago, United States
🇯🇵 Osaka, Japan
Travel Between:

$911

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Nov - Nov 2026
💰 $455
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$706

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Oct - Oct 2026
💰 $353
🇺🇸 Chicago, United States
🇭🇰 Hong Kong, Hong Kong SAR China
Travel Between:

$498

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Apr - Apr 2027
💰 $249
🇺🇸 Chicago, United States
🇳🇴 Stavanger, Norway
Travel Between: