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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$698 to 🇵🇭 Manila, Philippines $517 to 🇨🇱 Santiago, Chile $237 to 🇵🇷 San Juan, Puerto Rico See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$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:

$775

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Nov - Nov 2026
💰 $387
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$467

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Mar - Mar 2026
💰 $233
🇺🇸 Chicago, United States
🇨🇭 Zurich, Switzerland
Travel Between:

$561

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Apr - Apr 2026
💰 $280
🇺🇸 Chicago, United States
🇨🇱 Santiago, Chile
Travel Between:

$458

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Apr - Apr 2026
💰 $229
🇺🇸 Chicago, United States
🇪🇪 Tallinn, Estonia
Travel Between:

$538

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Aug - Aug 2026
💰 $269
🇺🇸 Chicago, United States
🇲🇹 Luqa, Malta
Travel Between:

$472

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Aug - Aug 2026
💰 $236
🇺🇸 Chicago, United States
🇮🇪 Cork, Ireland
Travel Between:

$862

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Feb - Feb 2026
💰 $431
🇺🇸 Chicago, United States
🇳🇿 Auckland, New Zealand
Travel Between:

$150

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Feb - Mar 2026
💰 $75
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$679

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Apr - Apr 2026
💰 $339
🇺🇸 Chicago, United States
🇦🇪 Dubai, United Arab Emirates
Travel Between:

$438

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Apr - Apr 2026
💰 $219
🇺🇸 Chicago, United States
🇪🇸 Ibiza, Spain
Travel Between:

$487

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Apr - Apr 2026
💰 $243
🇺🇸 Chicago, United States
🇧🇪 Brussels, Belgium
Travel Between:

$448

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Aug - Aug 2026
💰 $224
🇺🇸 Chicago, United States
🇬🇧 Inverness, United Kingdom
Travel Between:

$308

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Mar - Mar 2026
💰 $154
🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia
Travel Between:

$437

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Apr - Apr 2026
💰 $218
🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal
Travel Between: