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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$882 to 🇮🇳 New Delhi, India $894 to 🇻🇳 Ho Chi Minh City, Vietnam $335 to 🇩🇴 Punta Cana, Dominican Republic See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$882

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Sep - Sep 2026
💰 $441
🇺🇸 Chicago, United States
🇮🇳 New Delhi, India
Travel Between:

$894

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Sep - Sep 2026
💰 $447
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$335

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Aug - Aug 2026
💰 $167
🇺🇸 Chicago, United States
🇩🇴 Punta Cana, Dominican Republic
Travel Between:

$812

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Jan - Jan 2027
💰 $406
🇺🇸 Chicago, United States
🇮🇳 Mumbai, India
Travel Between:

$399

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Sep - Sep 2026
💰 $199
🇺🇸 Chicago, United States
🇸🇽 Saint Martin, Sint Maarten
Travel Between:

$368

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Nov - Nov 2026
💰 $184
🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia
Travel Between:

$594

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Nov - Nov 2026
💰 $297
🇺🇸 Chicago, United States
🇳🇴 Bergen, Norway
Travel Between:

$304

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Sep - Sep 2026
💰 $152
🇺🇸 Chicago, United States
🇬🇹 Guatemala City, Guatemala
Travel Between:

$885

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Nov - Nov 2026
💰 $442
🇺🇸 Chicago, United States
🇳🇿 Auckland, New Zealand
Travel Between:

$378

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Nov - Nov 2026
💰 $189
🇺🇸 Chicago, United States
🇩🇴 Santo Domingo, Dominican Republic
Travel Between:

$227

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Aug - Aug 2026
💰 $113
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$899

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Nov - Nov 2026
💰 $449
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$281

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Aug - Sep 2026
💰 $140
🇺🇸 Chicago, United States
🇨🇦 Calgary, Canada
Travel Between:

$378

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Jul - Jul 2026
💰 $189
🇺🇸 Chicago, United States
🇨🇴 Barranquilla, Colombia
Travel Between:

$613

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Oct - Oct 2026
💰 $306
🇺🇸 Chicago, United States
🇵🇱 Gdansk, Poland
Travel Between:

$894

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Sep - Sep 2026
💰 $447
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$323

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Nov - Nov 2026
💰 $161
🇺🇸 Chicago, United States
🇯🇲 Montego Bay, Jamaica
Travel Between:

$612

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Jan - Jan 2027
💰 $306
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$373

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Sep - Sep 2026
💰 $186
🇺🇸 Chicago, United States
🇺🇸 Anchorage, United States
Travel Between:

$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: