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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$333 to 🇺🇸 Kahului, United States $859 to 🇳🇿 Auckland, New Zealand $419 to 🇮🇪 Dublin, Ireland See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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Flights Options
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Destination Airport(s)
Departure Country Pro Only
Destination Country Pro Only
Flights Under Pro Only

$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:

$290

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

$444

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Jan - Jan 2026
💰 $222
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$284

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Nov - Nov 2025
💰 $142
🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia
Travel Between:

$111

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Jan - Jan 2026
💰 $55
🇺🇸 Chicago, United States
🇺🇸 New Orleans, United States
Travel Between:

$469

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Mar - Mar 2026
💰 $234
🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland
Travel Between:

$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: