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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$455 to 🇫🇷 Paris, France $589 to 🇹🇼 Kaohsiung City, Taiwan $424 to 🇦🇹 Vienna, Austria See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$455

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Oct - Oct 2025
💰 $227
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between:

$589

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Nov - Nov 2025
💰 $294
🇺🇸 Chicago, United States
🇹🇼 Kaohsiung City, Taiwan
Travel Between:

$424

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Nov - Nov 2025
💰 $212
🇺🇸 Chicago, United States
🇦🇹 Vienna, Austria
Travel Between:

$386

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Nov - Nov 2025
💰 $193
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between:

$367

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Oct - Oct 2025
💰 $183
🇺🇸 Chicago, United States
🇸🇪 Stockholm, Sweden
Travel Between:

$123

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Oct - Oct 2025
💰 $61
🇺🇸 Chicago, United States
🇨🇦 Vancouver, Canada
Travel Between:

$405

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Oct - Oct 2025
💰 $202
🇺🇸 Chicago, United States
🇨🇭 Zurich, Switzerland
Travel Between:

$385

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Oct - Oct 2025
💰 $192
🇺🇸 Chicago, United States
🇵🇱 Warsaw, Poland
Travel Between:

$456

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Oct - Oct 2025
💰 $228
🇺🇸 Chicago, United States
🇳🇱 Amsterdam, Netherlands
Travel Between:

$396

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Jan - Jan 2026
💰 $198
🇺🇸 Chicago, United States
🇮🇹 Milan, Italy
Travel Between:

$631

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Sep - Sep 2025
💰 $315
🇺🇸 Chicago, United States
🇮🇩 Jakarta, Indonesia
Travel Between:

$254

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Nov - Nov 2025
💰 $127
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$409

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Nov - Nov 2025
💰 $204
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between:

$199

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Oct - Oct 2025
💰 $99
🇺🇸 Chicago, United States
🇨🇦 Vancouver, Canada
Travel Between:

$701

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Nov - Nov 2025
💰 $350
🇺🇸 Chicago, United States
🇹🇼 Kaohsiung City, Taiwan
Travel Between:

$669

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Nov - Nov 2025
💰 $334
🇺🇸 Chicago, United States
🇹🇼 Taipei, Taiwan
Travel Between:

$657

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Nov - Nov 2025
💰 $328
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$117

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Nov - Nov 2025
💰 $58
🇺🇸 Chicago, United States
🇺🇸 San Diego, United States
Travel Between:

$735

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Nov - Dec 2025
💰 $367
🇺🇸 Chicago, United States
🇳🇿 Auckland, New Zealand
Travel Between:

$234

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Oct - Oct 2025
💰 $117
🇺🇸 Chicago, United States
🇳🇮 Managua, Nicaragua
Travel Between:

$408

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Nov - Nov 2025
💰 $204
🇺🇸 Chicago, United States
🇳🇴 Oslo, Norway
Travel Between:

$450

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Dec - Dec 2025
💰 $225
🇺🇸 Chicago, United States
🇮🇹 Napoli, Italy
Travel Between:

$749

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Oct - Oct 2025
💰 $374
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$474

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Nov - Nov 2025
💰 $237
🇺🇸 Chicago, United States
🇬🇷 Athens, Greece
Travel Between: