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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$396 to 🇨🇭 Geneva, Switzerland $384 to 🇮🇹 Rome, Italy $352 to 🇪🇸 Madrid, Spain See more deals from Chicago

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Destination Country Pro Only
Flights Under Pro Only

$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:

$2,909

*** - *** 2025 / *** - *** 2025 / *** - *** 2025
💰 $991 ⚡
🇺🇸 Chicago, United States
🇭🇷 Zagreb, Croatia
Travel Between: âš¡ Upgrade to premium plan to get access to travel dates and more.

$187

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Sep - Sep 2025
💰 $93
🇺🇸 Chicago, United States
🇨🇦 Montreal, Canada
Travel Between:

$127

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Dec - Dec 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $133
🇺🇸 Chicago, United States
🇺🇸 Memphis, United States
Travel Between: 01 August 2025 To 06 August 2025

$870

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Oct - Oct 2025
💰 $435
🇺🇸 Chicago, United States
🇻🇳 Ho Chi Minh City, Vietnam
Travel Between:

$181

View Deal
Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025 / Dec - Dec 2025
💰 $274
🇺🇸 Chicago, United States
🇺🇸 Portland, United States
Travel Between: 01 August 2025 To 06 August 2025

$157

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Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $183
🇺🇸 Chicago, United States
🇺🇸 Richmond, United States
Travel Between: 01 August 2025 To 06 August 2025

$157

View Deal
Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025 / Nov - Nov 2025
💰 $193
🇺🇸 Chicago, United States
🇺🇸 Jacksonville, United States
Travel Between: 01 August 2025 To 06 August 2025

$127

View Deal
Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025 / Nov - Nov 2025
💰 $213
🇺🇸 Chicago, United States
🇺🇸 Buffalo, United States
Travel Between: 01 August 2025 To 06 August 2025

$769

View Deal
Nov - Nov 2025
💰 $384
🇺🇸 Chicago, United States
🇹🇼 Kaohsiung City, Taiwan
Travel Between:

$309

View Deal
Sep - Sep 2025
💰 $154
🇺🇸 Chicago, United States
🇨🇷 San Jose, Costa Rica
Travel Between:

$170

View Deal
Sep - Sep 2025 / Aug - Aug 2025 / Dec - Dec 2025
💰 $145
🇺🇸 Chicago, United States
🇺🇸 Santa Ana, United States
Travel Between: 01 August 2025 To 06 August 2025

$148

View Deal
Aug - Aug 2025 / Dec - Dec 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025
💰 $147
🇺🇸 Chicago, United States
🇺🇸 San Diego, United States
Travel Between: 01 August 2025 To 06 August 2025

$163

View Deal
Dec - Dec 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $217
🇺🇸 Chicago, United States
🇺🇸 Salt Lake City, United States
Travel Between: 01 August 2025 To 06 August 2025

$127

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Aug - Aug 2025 / Dec - Dec 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025
💰 $203
🇺🇸 Chicago, United States
🇺🇸 Norfolk, United States
Travel Between: 01 August 2025 To 06 August 2025

$109

View Deal
Dec - Dec 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $186
🇺🇸 Chicago, United States
🇺🇸 Seattle, United States
Travel Between: 01 August 2025 To 06 August 2025

$876

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Aug - Aug 2025
💰 $438
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$146

View Deal
Dec - Dec 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $229
🇺🇸 Chicago, United States
🇺🇸 Austin, United States
Travel Between: 01 August 2025 To 06 August 2025

$181

View Deal
Aug - Aug 2025 / Dec - Dec 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025
💰 $129
🇺🇸 Chicago, United States
🇺🇸 Ontario, United States
Travel Between: 01 August 2025 To 06 August 2025

$145

View Deal
Sep - Sep 2025 / Aug - Aug 2025 / Dec - Dec 2025 / Nov - Nov 2025 / Oct - Oct 2025
💰 $150
🇺🇸 Chicago, United States
🇺🇸 Charleston, United States
Travel Between: 01 August 2025 To 06 August 2025

$181

View Deal
Dec - Dec 2025 / Nov - Nov 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $224
🇺🇸 Chicago, United States
🇺🇸 Sacramento, United States
Travel Between: 01 August 2025 To 06 August 2025