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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$511 to 🇮🇹 Napoli, Italy $476 to 🇪🇸 Barcelona, Spain $497 to 🇵🇹 Porto, Portugal See more deals from Chicago

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$511

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Nov - Nov 2025
💰 $255
🇺🇸 Chicago, United States
🇮🇹 Napoli, Italy
Travel Between:

$476

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Sep - Oct 2025
💰 $238
🇺🇸 Chicago, United States
🇪🇸 Barcelona, Spain
Travel Between:

$497

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Jan - Jan 2026
💰 $248
🇺🇸 Chicago, United States
🇵🇹 Porto, Portugal
Travel Between:

$163

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Jul - Jul 2025
💰 $81
🇺🇸 Chicago, United States
🇺🇸 San Diego, United States
Travel Between:

$417

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Sep - Sep 2025
💰 $208
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between:

$470

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Sep - Sep 2025
💰 $235
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between:

$784

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Sep - Sep 2025
💰 $392
🇺🇸 Chicago, United States
🇲🇾 Kuala Lumpur, Malaysia
Travel Between:

$505

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Nov - Nov 2025
💰 $252
🇺🇸 Chicago, United States
🇧🇷 Florianopolis, Brazil
Travel Between:

$803

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Aug - Sep 2025
💰 $401
🇺🇸 Chicago, United States
🇸🇬 Singapore, Singapore
Travel Between:

$516

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Sep - Oct 2025
💰 $258
🇺🇸 Chicago, United States
🇪🇸 Barcelona, Spain
Travel Between:

$752

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Aug - Sep 2025
💰 $376
🇺🇸 Chicago, United States
🇲🇾 Kuala Lumpur, Malaysia
Travel Between:

$311

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May - May 2025
💰 $155
🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia
Travel Between:

$436

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Jun - Jun 2025
💰 $218
🇺🇸 Chicago, United States
🇧🇷 Sao Paulo, Brazil
Travel Between:

$423

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Aug - Aug 2025
💰 $211
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between:

$675

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Aug - Sep 2025
💰 $337
🇺🇸 Chicago, United States
🇹🇼 Taipei, Taiwan
Travel Between:

$450

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Aug - Aug 2025
💰 $225
🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland
Travel Between:

$432

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Sep - Sep 2025
💰 $216
🇺🇸 Chicago, United States
🇪🇸 Madrid, Spain
Travel Between:

$417

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Sep - Sep 2025
💰 $208
🇺🇸 Chicago, United States
🇸🇪 Stockholm, Sweden
Travel Between:

$416

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Oct - Nov 2025
💰 $208
🇺🇸 Chicago, United States
🇮🇹 Milan, Italy
Travel Between:

$415

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Sep - Sep 2025
💰 $207
🇺🇸 Chicago, United States
🇨🇭 Zurich, Switzerland
Travel Between:

$467

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Sep - Sep 2025
💰 $233
🇺🇸 Chicago, United States
🇳🇴 Oslo, Norway
Travel Between:

$415

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Aug - Sep 2025
💰 $207
🇺🇸 Chicago, United States
🇳🇱 Amsterdam, Netherlands
Travel Between:

$496

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Oct - Oct 2025
💰 $453
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between: 10 October 2025 To 13 October 2025

$420

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Oct - Oct 2025
💰 $210
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between: