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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$749 to 🇹🇼 Taipei, Taiwan $500 to 🇧🇷 Rio De Janeiro, Brazil $287 to 🇨🇴 Rionegro, Colombia See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$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:

$444

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Jan - Jan 2026
💰 $222
🇺🇸 Chicago, United States
🇮🇹 Milan, Italy
Travel Between:

$444

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Mar - Mar 2026
💰 $222
🇺🇸 Chicago, United States
🇵🇹 Porto, Portugal
Travel Between:

$456

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Feb - Feb 2026
💰 $228
🇺🇸 Chicago, United States
🇮🇹 Rome, Italy
Travel Between:

$368

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Mar - Mar 2026
💰 $184
🇺🇸 Chicago, United States
🇸🇪 Stockholm, Sweden
Travel Between:

$379

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Jan - Jan 2026
💰 $189
🇺🇸 Chicago, United States
🇺🇸 Kahului, United States
Travel Between:

$698

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Sep - Sep 2026
💰 $349
🇺🇸 Chicago, United States
🇦🇪 Dubai, United Arab Emirates
Travel Between:

$155

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Jan - Jan 2026
💰 $77
🇺🇸 Chicago, United States
🇺🇸 San Diego, United States
Travel Between:

$149

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Feb - Feb 2026
💰 $74
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$333

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Jan - Jan 2026
💰 $166
🇺🇸 Chicago, United States
🇺🇸 Kahului, United States
Travel Between:

$859

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Jan - Jan 2026
💰 $429
🇺🇸 Chicago, United States
🇳🇿 Auckland, New Zealand
Travel Between:

$419

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Mar - Mar 2026
💰 $209
🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland
Travel Between:

$411

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Mar - Mar 2026
💰 $205
🇺🇸 Chicago, United States
🇳🇴 Oslo, Norway
Travel Between:

$485

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Mar - Mar 2026
💰 $242
🇺🇸 Chicago, United States
🇬🇷 Athens, Greece
Travel Between:

$659

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Jan - Jan 2026
💰 $329
🇺🇸 Chicago, United States
🇮🇳 New Delhi, India
Travel Between:

$863

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Apr - Apr 2026
💰 $431
🇺🇸 Chicago, United States
🇮🇩 Denpasar-Bali Island, Indonesia
Travel Between:

$376

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Mar - Mar 2026
💰 $188
🇺🇸 Chicago, United States
🇸🇪 Stockholm, Sweden
Travel Between:

$892

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Feb - Feb 2026
💰 $446
🇺🇸 Chicago, United States
🇰🇪 Nairobi, Kenya
Travel Between: