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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$833 to 🇹🇭 Bangkok, Thailand $861 to 🇵🇭 Manila, Philippines $883 to 🇹🇭 Chiang Mai, Thailand See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$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:

$470

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Oct - Oct 2026
💰 $235
🇺🇸 Chicago, United States
🇺🇸 Kailua/Kona, United States
Travel Between:

$808

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Nov - Nov 2026
💰 $404
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$496

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Mar - Mar 2027
💰 $248
🇺🇸 Chicago, United States
🇳🇴 Oslo, Norway
Travel Between:

$407

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Mar - Mar 2027
💰 $203
🇺🇸 Chicago, United States
🇧🇪 Brussels, Belgium
Travel Between:

$497

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Mar - Mar 2027
💰 $248
🇺🇸 Chicago, United States
🇩🇰 Copenhagen, Denmark
Travel Between:

$497

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Mar - Mar 2027
💰 $248
🇺🇸 Chicago, United States
🇸🇪 Stockholm, Sweden
Travel Between:

$591

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Apr - Apr 2027
💰 $295
🇺🇸 Chicago, United States
🇪🇸 Bilbao, Spain
Travel Between:

$388

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Nov - Nov 2026
💰 $194
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between:

$588

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Feb - Feb 2027
💰 $294
🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal
Travel Between:

$584

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Feb - Feb 2027
💰 $292
🇺🇸 Chicago, United States
🇮🇹 Napoli, Italy
Travel Between:

$575

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Nov - Nov 2026
💰 $287
🇺🇸 Chicago, United States
🇵🇹 Porto, Portugal
Travel Between:

$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
Travel Between:

$509

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