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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$382 to 🇪🇨 Guayaquil, Ecuador $937 to 🇵🇭 Manila, Philippines $610 to 🇨🇭 Zurich, Switzerland See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$382

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Sep - Sep 2026
💰 $191
🇺🇸 Chicago, United States
🇪🇨 Guayaquil, Ecuador
Travel Between:

$937

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Sep - Sep 2026
💰 $468
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$610

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Nov - Nov 2026
💰 $305
🇺🇸 Chicago, United States
🇨🇭 Zurich, Switzerland
Travel Between:

$598

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Oct - Oct 2026
💰 $299
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between:

$591

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Oct - Nov 2026
💰 $295
🇺🇸 Chicago, United States
🇮🇹 Milan, Italy
Travel Between:

$578

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Oct - Oct 2026
💰 $289
🇺🇸 Chicago, United States
🇱🇻 Riga, Latvia
Travel Between:

$578

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Oct - Oct 2026
💰 $289
🇺🇸 Chicago, United States
🇱🇹 Vilnius, Lithuania
Travel Between:

$590

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Oct - Oct 2026
💰 $295
🇺🇸 Chicago, United States
🇵🇱 Warsaw, Poland
Travel Between:

$581

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Nov - Nov 2026
💰 $290
🇺🇸 Chicago, United States
🇪🇪 Tallinn, Estonia
Travel Between:

$722

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Nov - Nov 2026
💰 $361
🇺🇸 Chicago, United States
🇮🇳 Mumbai, India
Travel Between:

$902

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Sep - Sep 2026
💰 $451
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$411

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Sep - Sep 2026
💰 $205
🇺🇸 Chicago, United States
🇪🇨 Guayaquil, Ecuador
Travel Between:

$337

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Nov - Nov 2026
💰 $168
🇺🇸 Chicago, United States
🇯🇲 Montego Bay, Jamaica
Travel Between:

$610

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Jan - Jan 2027
💰 $305
🇺🇸 Chicago, United States
🇱🇹 Vilnius, Lithuania
Travel Between:

$307

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Nov - Nov 2026
💰 $153
🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia
Travel Between:

$813

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Nov - Nov 2026
💰 $406
🇺🇸 Chicago, United States
🇮🇳 Mumbai, India
Travel Between:

$352

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Aug - Aug 2026
💰 $176
🇺🇸 Chicago, United States
🇩🇴 Santiago, Dominican Republic
Travel Between:

$850

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Aug - Aug 2026
💰 $425
🇺🇸 Chicago, United States
🇫🇯 Nadi, Fiji
Travel Between:

$222

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Aug - Aug 2026
💰 $111
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$611

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Oct - Oct 2026
💰 $305
🇺🇸 Chicago, United States
🇱🇻 Riga, Latvia
Travel Between:

$614

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Sep - Oct 2026
💰 $307
🇺🇸 Chicago, United States
🇵🇱 Gdansk, Poland
Travel Between:

$358

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Nov - Nov 2026
💰 $179
🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia
Travel Between:

$802

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Nov - Nov 2026
💰 $401
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$963

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Nov - Nov 2026
💰 $481
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between: