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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$706 to 🇭🇰 Hong Kong, Hong Kong SAR China $498 to 🇳🇴 Stavanger, Norway $883 to 🇯🇵 Osaka, Japan See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$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:

$883

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Sep - Sep 2026
💰 $441
🇺🇸 Chicago, United States
🇯🇵 Osaka, Japan
Travel Between:

$701

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Nov - Nov 2026
💰 $350
🇺🇸 Chicago, United States
🇪🇬 Cairo, Egypt
Travel Between:

$404

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Nov - Nov 2026
💰 $202
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between:

$510

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Sep - Sep 2026
💰 $255
🇺🇸 Chicago, United States
🇺🇸 Honolulu, United States
Travel Between:

$375

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Nov - Nov 2026
💰 $187
🇺🇸 Chicago, United States
🇩🇴 Punta Cana, Dominican Republic
Travel Between:

$438

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Nov - Nov 2026
💰 $219
🇺🇸 Chicago, United States
🇺🇸 Kailua/Kona, United States
Travel Between:

$806

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Nov - Nov 2026
💰 $403
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$662

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Jan - Jan 2027
💰 $331
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$346

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Apr - Apr 2027
💰 $173
🇺🇸 Chicago, United States
🇨🇷 San Jose, Costa Rica
Travel Between:

$357

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Jan - Jan 2027
💰 $178
🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia
Travel Between:

$386

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Mar - Mar 2027
💰 $193
🇺🇸 Chicago, United States
🇸🇪 Gothenburg, Sweden
Travel Between:

$426

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Mar - Mar 2027
💰 $213
🇺🇸 Chicago, United States
🇳🇴 Oslo, Norway
Travel Between:

$758

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Nov - Nov 2026
💰 $379
🇺🇸 Chicago, United States
🇮🇳 Chennai, India
Travel Between:

$872

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Sep - Sep 2026
💰 $436
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$859

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Sep - Sep 2026
💰 $429
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$427

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💰 $213
🇺🇸 Chicago, United States
🇳🇴 Trondheim, Norway
Travel Between:

$862

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Sep - Sep 2026
💰 $431
🇺🇸 Chicago, United States
🇺🇿 Tashkent, Uzbekistan
Travel Between:

$830

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Sep - Sep 2026
💰 $415
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$378

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Nov - Nov 2026
💰 $189
🇺🇸 Chicago, United States
🇺🇸 Kahului, United States
Travel Between:

$796

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Sep - Sep 2026
💰 $398
🇺🇸 Chicago, United States
🇱🇰 Colombo, Sri Lanka
Travel Between:

$919

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Nov - Nov 2026
💰 $459
🇺🇸 Chicago, United States
🇵🇭 Lapu-Lapu City, Philippines
Travel Between:

$487

View Deal
Oct - Oct 2026
💰 $243
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between: