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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$279 to 🇻🇮 Charlotte Amalie, U.S. Virgin Islands $775 to 🇻🇳 Ho Chi Minh City, Vietnam $147 to 🇺🇸 Columbia, United States 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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Flights Under Pro Only

$279

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Jan - Jan 2026
💰 $139
🇺🇸 Chicago, United States
🇻🇮 Charlotte Amalie, U.S. Virgin Islands
Travel Between:

$775

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Nov - Nov 2025
💰 $387
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$147

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Aug - Aug 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025
💰 $163
🇺🇸 Chicago, United States
🇺🇸 Columbia, United States
Travel Between: 01 August 2025 To 06 August 2025

$448

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Nov - Nov 2025
💰 $224
🇺🇸 Chicago, United States
🇩🇪 Dusseldorf, Germany
Travel Between:

$435

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Aug - Aug 2025
💰 $217
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between:

$229

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Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025 / Jul - Jul 2025
💰 $161
🇺🇸 Chicago, United States
🇺🇸 Bangor, United States
Travel Between: 01 July 2025 To 06 July 2025

$515

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Nov - Nov 2025
💰 $257
🇺🇸 Chicago, United States
🇬🇷 Athens, Greece
Travel Between:

$748

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Aug - Sep 2025
💰 $374
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$498

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Nov - Nov 2025
💰 $249
🇺🇸 Chicago, United States
🇵🇹 Porto, Portugal
Travel Between:

$77

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Aug - Aug 2025 / Dec - Dec 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025
💰 $228
🇺🇸 Chicago, United States
🇺🇸 Minneapolis, United States
Travel Between: 01 August 2025 To 06 August 2025

$587

*** - *** 2025 / *** - *** 2025 / *** - *** 2025 / *** - *** 2025 / *** - *** 2025
💰 $193 ⚡
🇺🇸 Chicago, United States
🇺🇸 Jackson, United States
Travel Between: âš¡ Upgrade to premium plan to get access to travel dates and more.

$761

*** - *** 2025 / *** - *** 2025 / *** - *** 2025
💰 $739 ⚡
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between: âš¡ Upgrade to premium plan to get access to travel dates and more.

$738

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Nov - Nov 2025
💰 $369
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$189

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Mar - Mar 2026 / Feb - Feb 2026 / Jan - Jan 2026 / Dec - Dec 2025 / May - May 2026 / Jul - Jul 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $106
🇺🇸 Chicago, United States
🇺🇸 Chattanooga, United States
Travel Between: 01 July 2025 To 06 July 2025

$179

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Jul - Jul 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025 / Mar - Mar 2026 / Jan - Jan 2026 / Dec - Dec 2025
💰 $81
🇺🇸 Chicago, United States
🇺🇸 Duluth, United States
Travel Between: 01 July 2025 To 06 July 2025

$197

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Sep - Sep 2025 / Aug - Aug 2025 / Nov - Nov 2025 / Oct - Oct 2025
💰 $98
🇺🇸 Chicago, United States
🇺🇸 Little Rock, United States
Travel Between: 01 August 2025 To 06 August 2025

$191

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Sep - Sep 2025 / Aug - Aug 2025 / Oct - Oct 2025
💰 $154
🇺🇸 Chicago, United States
🇺🇸 Manchester, United States
Travel Between: 01 August 2025 To 06 August 2025

$197

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Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $103
🇺🇸 Chicago, United States
🇺🇸 Birmingham, United States
Travel Between: 01 August 2025 To 06 August 2025

$197

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Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $113
🇺🇸 Chicago, United States
🇺🇸 Tulsa, United States
Travel Between: 01 August 2025 To 06 August 2025

$197

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Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $103
🇺🇸 Chicago, United States
🇺🇸 Wichita, United States
Travel Between: 01 August 2025 To 06 August 2025

$396

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Nov - Nov 2025
💰 $198
🇺🇸 Chicago, United States
🇨🇭 Geneva, Switzerland
Travel Between:

$384

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Nov - Nov 2025
💰 $192
🇺🇸 Chicago, United States
🇮🇹 Rome, Italy
Travel Between:

$352

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Oct - Oct 2025
💰 $176
🇺🇸 Chicago, United States
🇪🇸 Madrid, Spain
Travel Between:

$289

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Nov - Nov 2025
💰 $144
🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia
Travel Between: