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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$796 to 🇹🇭 Bangkok, Thailand $416 to 🇸🇪 Gothenburg, Sweden $465 to 🇨🇭 Zurich, Switzerland See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$796

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Mar - Mar 2026
💰 $398
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$416

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Mar - Mar 2026
💰 $208
🇺🇸 Chicago, United States
🇸🇪 Gothenburg, Sweden
Travel Between:

$465

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Mar - Mar 2026
💰 $232
🇺🇸 Chicago, United States
🇨🇭 Zurich, Switzerland
Travel Between:

$860

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Apr - Apr 2025
💰 $430
🇺🇸 Chicago, United States
🇺🇬 Kampala, Uganda
Travel Between:

$710

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Feb - Feb 2026
💰 $355
🇺🇸 Chicago, United States
🇮🇳 Chennai, India
Travel Between:

$470

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Mar - Mar 2026
💰 $235
🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland
Travel Between:

$471

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Aug - Aug 2026
💰 $235
🇺🇸 Chicago, United States
🇮🇪 Cork, Ireland
Travel Between:

$537

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Aug - Aug 2026
💰 $268
🇺🇸 Chicago, United States
🇲🇹 Luqa, Malta
Travel Between:

$157

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Jan - Jan 2026
💰 $78
🇺🇸 Chicago, United States
🇺🇸 San Diego, United States
Travel Between:

$309

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

$858

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Feb - Feb 2026
💰 $429
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$861

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Jan - Jan 2026
💰 $430
🇺🇸 Chicago, United States
🇳🇿 Auckland, New Zealand
Travel Between:

$403

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Jan - Jan 2026
💰 $201
🇺🇸 Chicago, United States
🇺🇸 Honolulu, United States
Travel Between:

$421

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Jan - Jan 2026
💰 $210
🇺🇸 Chicago, United States
🇺🇸 Kailua/Kona, United States
Travel Between:

$473

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Mar - Mar 2026
💰 $236
🇺🇸 Chicago, United States
🇪🇸 Madrid, Spain
Travel Between:

$474

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Jan - Jan 2026
💰 $237
🇺🇸 Chicago, United States
🇦🇹 Vienna, Austria
Travel Between:

$677

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Jan - Jan 2026
💰 $338
🇺🇸 Chicago, United States
🇦🇪 Dubai, United Arab Emirates
Travel Between:

$749

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Feb - Feb 2026
💰 $374
🇺🇸 Chicago, United States
🇹🇼 Taipei, Taiwan
Travel Between:

$500

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Jan - Jan 2026
💰 $250
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$287

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Jan - Jan 2026
💰 $143
🇺🇸 Chicago, United States
🇨🇴 Rionegro, Colombia
Travel Between:

$290

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Jan - Jan 2026
💰 $145
🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia
Travel Between:

$748

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Feb - Feb 2026
💰 $374
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$449

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Mar - Mar 2026
💰 $224
🇺🇸 Chicago, United States
🇮🇹 Napoli, Italy
Travel Between:

$453

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Mar - Mar 2026
💰 $226
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between: