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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$614 to 🇵🇱 Gdansk, Poland $358 to 🇨🇴 Cartagena, Colombia $802 to 🇸🇬 Singapore, Singapore See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$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:

$370

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Oct - Oct 2026
💰 $185
🇺🇸 Chicago, United States
🇨🇷 San Jose, Costa Rica
Travel Between:

$963

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

$602

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Jan - Jan 2027
💰 $301
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$947

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Nov - Nov 2026
💰 $473
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$360

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Nov - Nov 2026
💰 $180
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between:

$494

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Sep - Sep 2026
💰 $247
🇺🇸 Chicago, United States
🇺🇸 Kailua/Kona, United States
Travel Between:

$494

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Sep - Sep 2026
💰 $247
🇺🇸 Chicago, United States
🇺🇸 Honolulu, United States
Travel Between:

$254

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Aug - Sep 2026
💰 $127
🇺🇸 Chicago, United States
🇨🇦 Calgary, Canada
Travel Between:

$367

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May - May 2026
💰 $183
🇺🇸 Chicago, United States
🇺🇸 Anchorage, United States
Travel Between:

$516

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Oct - Oct 2026
💰 $258
🇺🇸 Chicago, United States
🇫🇴 Vagar, Faroe Islands
Travel Between:

$561

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Sep - Sep 2026
💰 $280
🇺🇸 Chicago, United States
🇮🇳 New Delhi, India
Travel Between:

$176

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Sep - Sep 2026
💰 $88
🇺🇸 Chicago, United States
🇺🇸 Eugene, United States
Travel Between:

$318

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Sep - Sep 2026
💰 $159
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between:

$454

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May - May 2026
💰 $227
🇺🇸 Chicago, United States
🇪🇨 Quito, Ecuador
Travel Between:

$455

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Jan - Jan 2026
💰 $227
🇺🇸 Chicago, United States
🇧🇷 Belo Horizonte, Brazil
Travel Between:

$367

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Nov - Nov 2026
💰 $183
🇺🇸 Chicago, United States
🇳🇮 Managua, Nicaragua
Travel Between:

$321

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Nov - Nov 2026
💰 $160
🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia
Travel Between:

$773

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Nov - Nov 2026
💰 $386
🇺🇸 Chicago, United States
🇮🇳 Mumbai, India
Travel Between:

$590

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Jan - Jan 2027
💰 $295
🇺🇸 Chicago, United States
🇱🇹 Vilnius, Lithuania
Travel Between:

$618

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Nov - Nov 2026
💰 $309
🇺🇸 Chicago, United States
🇧🇷 Porto Alegre, Brazil
Travel Between: