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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$424 to 🇺🇸 Lihue, United States $479 to 🇨🇭 Zurich, Switzerland $460 to 🇪🇪 Tallinn, Estonia See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$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:

$460

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Apr - Apr 2026
💰 $230
🇺🇸 Chicago, United States
🇪🇪 Tallinn, Estonia
Travel Between:

$750

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Nov - Nov 2026
💰 $375
🇺🇸 Chicago, United States
🇹🇼 Taipei, Taiwan
Travel Between:

$559

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Apr - Apr 2026
💰 $279
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$277

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Apr - Apr 2026
💰 $138
🇺🇸 Chicago, United States
🇯🇲 Montego Bay, Jamaica
Travel Between:

$308

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Mar - Mar 2026
💰 $154
🇺🇸 Chicago, United States
🇺🇸 Anchorage, United States
Travel Between:

$360

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Apr - Apr 2026
💰 $180
🇺🇸 Chicago, United States
🇺🇸 Honolulu, United States
Travel Between:

$323

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

$764

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Nov - Nov 2026
💰 $382
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$579

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Mar - Mar 2026
💰 $289
🇺🇸 Chicago, United States
🇳🇿 Auckland, New Zealand
Travel Between:

$281

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May - May 2026
💰 $140
🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia
Travel Between:

$476

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Apr - Apr 2026
💰 $238
🇺🇸 Chicago, United States
🇪🇸 Madrid, Spain
Travel Between:

$849

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Nov - Nov 2026
💰 $424
🇺🇸 Chicago, United States
🇫🇯 Nadi, Fiji
Travel Between:

$698

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Oct - Oct 2026
💰 $349
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$517

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Apr - Apr 2026
💰 $258
🇺🇸 Chicago, United States
🇨🇱 Santiago, Chile
Travel Between:

$237

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Apr - Apr 2026
💰 $118
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$121

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Apr - Apr 2026
💰 $60
🇺🇸 Chicago, United States
🇺🇸 San Diego, United States
Travel Between:

$790

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Nov - Nov 2026
💰 $395
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$792

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Oct - Oct 2026
💰 $396
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$379

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Nov - Nov 2026
💰 $189
🇺🇸 Chicago, United States
🇸🇪 Stockholm, Sweden
Travel Between:

$676

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Apr - Apr 2026
💰 $338
🇺🇸 Chicago, United States
🇱🇰 Colombo, Sri Lanka
Travel Between:

$798

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Nov - Nov 2026
💰 $399
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$440

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Apr - Apr 2026
💰 $220
🇺🇸 Chicago, United States
🇧🇷 Sao Paulo, Brazil
Travel Between: