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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$378 to 🇮🇸 Reykjavik, Iceland $554 to 🇵🇭 Manila, Philippines $423 to 🇺🇸 Kailua/Kona, United States See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$378

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Jan - Jan 2026
💰 $189
🇺🇸 Chicago, United States
🇮🇸 Reykjavik, Iceland
Travel Between:

$554

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Nov - Nov 2025
💰 $277
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$423

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Jan - Jan 2026
💰 $211
🇺🇸 Chicago, United States
🇺🇸 Kailua/Kona, United States
Travel Between:

$263

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Dec - Dec 2025
💰 $131
🇺🇸 Chicago, United States
🇩🇴 Punta Cana, Dominican Republic
Travel Between:

$526

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Oct - Nov 2025
💰 $263
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$151

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Jan - Jan 2026
💰 $75
🇺🇸 Chicago, United States
🇺🇸 Palm Springs, United States
Travel Between:

$456

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Mar - Mar 2026
💰 $228
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between:

$103

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Jan - Jan 2026
💰 $51
🇺🇸 Chicago, United States
🇺🇸 San Diego, United States
Travel Between:

$666

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Nov - Nov 2025
💰 $333
🇺🇸 Chicago, United States
🇦🇪 Dubai, United Arab Emirates
Travel Between:

$348

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Aug - Aug 2026
💰 $174
🇺🇸 Chicago, United States
🇧🇷 Sao Paulo, Brazil
Travel Between:

$844

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Feb - Feb 2026
💰 $422
🇺🇸 Chicago, United States
🇦🇺 Sydney, Australia
Travel Between:

$469

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Nov - Nov 2025
💰 $234
🇺🇸 Chicago, United States
🇪🇸 Barcelona, Spain
Travel Between:

$435

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Jan - Jan 2026
💰 $217
🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal
Travel Between:

$197

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Jan - Jan 2026
💰 $98
🇺🇸 Chicago, United States
🇬🇹 Guatemala City, Guatemala
Travel Between:

$487

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Mar - Mar 2026
💰 $243
🇺🇸 Chicago, United States
🇫🇷 Nice, France
Travel Between:

$455

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Mar - Mar 2026
💰 $227
🇺🇸 Chicago, United States
🇳🇱 Amsterdam, Netherlands
Travel Between:

$398

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Mar - Mar 2026
💰 $199
🇺🇸 Chicago, United States
🇳🇴 Oslo, Norway
Travel Between:

$454

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Mar - Mar 2026
💰 $227
🇺🇸 Chicago, United States
🇦🇹 Vienna, Austria
Travel Between:

$399

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Oct - Oct 2025
💰 $199
🇺🇸 Chicago, United States
🇮🇸 Reykjavik, Iceland
Travel Between:

$766

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Jan - Jan 2026
💰 $383
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$357

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Jan - Jan 2026
💰 $178
🇺🇸 Chicago, United States
🇺🇸 Fairbanks, United States
Travel Between:

$262

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Nov - Nov 2025
💰 $131
🇺🇸 Chicago, United States
🇩🇴 Punta Cana, Dominican Republic
Travel Between:

$659

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Nov - Nov 2025
💰 $329
🇺🇸 Chicago, United States
🇮🇳 New Delhi, India
Travel Between:

$135

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Nov - Nov 2025
💰 $67
🇺🇸 Chicago, United States
🇺🇸 San Diego, United States
Travel Between: