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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$721 to 🇦🇪 Dubai, United Arab Emirates $760 to 🇮🇳 Mumbai, India $857 to 🇺🇿 Tashkent, Uzbekistan See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$721

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Jan - Jan 2027
💰 $360
🇺🇸 Chicago, United States
🇦🇪 Dubai, United Arab Emirates
Travel Between:

$760

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Mar - Mar 2027
💰 $380
🇺🇸 Chicago, United States
🇮🇳 Mumbai, India
Travel Between:

$857

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💰 $428
🇺🇸 Chicago, United States
🇺🇿 Tashkent, Uzbekistan
Travel Between:

$424

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Jan - Jan 2027
💰 $212
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between:

$553

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Feb - Feb 2027
💰 $276
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$467

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Nov - Nov 2026
💰 $233
🇺🇸 Chicago, United States
🇮🇸 Reykjavik, Iceland
Travel Between:

$451

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Dec - Dec 2026
💰 $225
🇺🇸 Chicago, United States
🇳🇱 Amsterdam, Netherlands
Travel Between:

$868

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Feb - Feb 2027
💰 $434
🇺🇸 Chicago, United States
🇻🇳 Da Nang, Vietnam
Travel Between:

$927

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Nov - Nov 2026
💰 $463
🇺🇸 Chicago, United States
🇰🇪 Nairobi, Kenya
Travel Between:

$862

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Jan - Jan 2027
💰 $431
🇺🇸 Chicago, United States
🇮🇩 Jakarta, Indonesia
Travel Between:

$365

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💰 $182
🇺🇸 Chicago, United States
🇩🇴 Punta Cana, Dominican Republic
Travel Between:

$191

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Nov - Nov 2026
💰 $95
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$811

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Jan - Jan 2027
💰 $405
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$858

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Jan - Jan 2027
💰 $429
🇺🇸 Chicago, United States
🇵🇭 Lapu-Lapu City, Philippines
Travel Between:

$833

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Feb - Feb 2027
💰 $416
🇺🇸 Chicago, United States
🇹🇭 Chiang Mai, Thailand
Travel Between:

$833

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Feb - Feb 2027
💰 $416
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$861

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Nov - Nov 2026
💰 $430
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$883

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Feb - Feb 2027
💰 $441
🇺🇸 Chicago, United States
🇹🇭 Chiang Mai, Thailand
Travel Between:

$882

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Feb - Feb 2027
💰 $441
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$920

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Jan - Jan 2027
💰 $460
🇺🇸 Chicago, United States
🇵🇭 Lapu-Lapu City, Philippines
Travel Between:

$896

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Sep - Sep 2026
💰 $448
🇺🇸 Chicago, United States
🇲🇾 Kuala Lumpur, Malaysia
Travel Between:

$867

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Nov - Nov 2026
💰 $433
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$465

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Nov - Nov 2026
💰 $232
🇺🇸 Chicago, United States
🇳🇴 Stavanger, Norway
Travel Between:

$465

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Feb - Feb 2027
💰 $232
🇺🇸 Chicago, United States
🇳🇴 Bergen, Norway
Travel Between: