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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$700 to 🇮🇳 New Delhi, India $363 to 🇨🇴 Cartagena, Colombia $349 to 🇧🇿 Belize City, Belize See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$700

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Sep - Sep 2026
💰 $350
🇺🇸 Chicago, United States
🇮🇳 New Delhi, India
Travel Between:

$363

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May - May 2026
💰 $181
🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia
Travel Between:

$349

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May - May 2026
💰 $174
🇺🇸 Chicago, United States
🇧🇿 Belize City, Belize
Travel Between:

$573

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Apr - Apr 2026
💰 $286
🇺🇸 Chicago, United States
🇨🇱 Santiago, Chile
Travel Between:

$383

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Apr - Apr 2026
💰 $191
🇺🇸 Chicago, United States
🇹🇹 Port of Spain, Trinidad & Tobago
Travel Between:

$317

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Apr - May 2026
💰 $158
🇺🇸 Chicago, United States
🇯🇲 Montego Bay, Jamaica
Travel Between:

$400

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Sep - Sep 2026
💰 $200
🇺🇸 Chicago, United States
🇺🇸 Honolulu, United States
Travel Between:

$514

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Apr - Apr 2026
💰 $257
🇺🇸 Chicago, United States
🇮🇸 Reykjavik, Iceland
Travel Between:

$795

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Sep - Sep 2026
💰 $397
🇺🇸 Chicago, United States
🇮🇳 Bangalore, India
Travel Between:

$913

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Nov - Nov 2026
💰 $456
🇺🇸 Chicago, United States
🇭🇰 Hong Kong, Hong Kong SAR China
Travel Between:

$319

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Apr - Apr 2026
💰 $159
🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia
Travel Between:

$743

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Nov - Nov 2026
💰 $371
🇺🇸 Chicago, United States
🇮🇳 Mumbai, India
Travel Between:

$447

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Jun - Jun 2026
💰 $223
🇺🇸 Chicago, United States
🇮🇸 Reykjavik, Iceland
Travel Between:

$793

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Nov - Nov 2026
💰 $396
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$700

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Nov - Nov 2026
💰 $350
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$768

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Nov - Nov 2026
💰 $384
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$476

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Sep - Sep 2026
💰 $238
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between:

$821

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Sep - Sep 2026
💰 $410
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$459

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Sep - Sep 2026
💰 $229
🇺🇸 Chicago, United States
🇵🇱 Gdansk, Poland
Travel Between:

$903

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Nov - Nov 2026
💰 $451
🇺🇸 Chicago, United States
🇰🇪 Nairobi, Kenya
Travel Between:

$380

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Nov - Nov 2026
💰 $190
🇺🇸 Chicago, United States
🇸🇪 Stockholm, Sweden
Travel Between:

$323

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Apr - Apr 2026
💰 $161
🇺🇸 Chicago, United States
🇨🇴 Rionegro, Colombia
Travel Between:

$424

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Oct - Oct 2026
💰 $212
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between:

$479

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Apr - Apr 2026
💰 $239
🇺🇸 Chicago, United States
🇨🇭 Zurich, Switzerland
Travel Between: