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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$455 to 🇧🇷 Belo Horizonte, Brazil $367 to 🇳🇮 Managua, Nicaragua $321 to 🇨🇴 Bogota, Colombia See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$455

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Jan - Jan 2026
💰 $227
🇺🇸 Chicago, United States
🇧🇷 Belo Horizonte, Brazil
Travel Between:

$367

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Nov - Nov 2026
💰 $183
🇺🇸 Chicago, United States
🇳🇮 Managua, Nicaragua
Travel Between:

$321

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Nov - Nov 2026
💰 $160
🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia
Travel Between:

$773

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Nov - Nov 2026
💰 $386
🇺🇸 Chicago, United States
🇮🇳 Mumbai, India
Travel Between:

$590

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Jan - Jan 2027
💰 $295
🇺🇸 Chicago, United States
🇱🇹 Vilnius, Lithuania
Travel Between:

$618

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Nov - Nov 2026
💰 $309
🇺🇸 Chicago, United States
🇧🇷 Porto Alegre, Brazil
Travel Between:

$217

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May - May 2026
💰 $108
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$848

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

$377

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May - May 2026
💰 $188
🇺🇸 Chicago, United States
🇺🇸 Anchorage, United States
Travel Between:

$247

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May - May 2026
💰 $123
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$333

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May - May 2026
💰 $166
🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia
Travel Between:

$563

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Nov - Nov 2026
💰 $281
🇺🇸 Chicago, United States
🇪🇪 Tallinn, Estonia
Travel Between:

$398

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May - May 2026
💰 $199
🇺🇸 Chicago, United States
🇺🇸 Fairbanks, United States
Travel Between:

$424

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

$845

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Sep - Sep 2026
💰 $422
🇺🇸 Chicago, United States
🇮🇳 Bangalore, India
Travel Between:

$307

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May - May 2026
💰 $153
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$470

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Apr - Apr 2026
💰 $235
🇺🇸 Chicago, United States
🇺🇸 Kahului, United States
Travel Between:

$342

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Oct - Oct 2026
💰 $171
🇺🇸 Chicago, United States
🇬🇹 Guatemala City, Guatemala
Travel Between:

$906

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Nov - Nov 2026
💰 $453
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$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: