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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$150 to 🇵🇷 San Juan, Puerto Rico $679 to 🇦🇪 Dubai, United Arab Emirates $438 to 🇪🇸 Ibiza, Spain See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$150

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Feb - Mar 2026
💰 $75
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between:

$679

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Apr - Apr 2026
💰 $339
🇺🇸 Chicago, United States
🇦🇪 Dubai, United Arab Emirates
Travel Between:

$438

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Apr - Apr 2026
💰 $219
🇺🇸 Chicago, United States
🇪🇸 Ibiza, Spain
Travel Between:

$487

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Apr - Apr 2026
💰 $243
🇺🇸 Chicago, United States
🇧🇪 Brussels, Belgium
Travel Between:

$448

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Aug - Aug 2026
💰 $224
🇺🇸 Chicago, United States
🇬🇧 Inverness, United Kingdom
Travel Between:

$308

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Mar - Mar 2026
💰 $154
🇺🇸 Chicago, United States
🇨🇴 Cartagena, Colombia
Travel Between:

$437

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Apr - Apr 2026
💰 $218
🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal
Travel Between:

$292

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Apr - Apr 2026
💰 $146
🇺🇸 Chicago, United States
🇨🇴 Rionegro, Colombia
Travel Between:

$276

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Feb - Feb 2026
💰 $138
🇺🇸 Chicago, United States
🇨🇴 Bogota, Colombia
Travel Between:

$458

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Mar - Mar 2026
💰 $229
🇺🇸 Chicago, United States
🇪🇸 Malaga, Spain
Travel Between:

$424

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Apr - Apr 2026
💰 $212
🇺🇸 Chicago, United States
🇪🇸 Madrid, Spain
Travel Between:

$441

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Mar - Mar 2026
💰 $220
🇺🇸 Chicago, United States
🇪🇸 Bilbao, Spain
Travel Between:

$764

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Feb - Feb 2026
💰 $382
🇺🇸 Chicago, United States
🇿🇦 Olifants River Bridge, South Africa
Travel Between:

$424

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Aug - Aug 2026
💰 $212
🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland
Travel Between:

$420

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Apr - Apr 2026
💰 $210
🇺🇸 Chicago, United States
🇪🇸 Barcelona, Spain
Travel Between:

$340

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Feb - Feb 2026
💰 $170
🇺🇸 Chicago, United States
🇺🇸 Honolulu, United States
Travel Between:

$336

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Feb - Feb 2026
💰 $168
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between:

$378

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May - May 2026
💰 $189
🇺🇸 Chicago, United States
🇸🇪 Stockholm, Sweden
Travel Between:

$377

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Mar - Mar 2026
💰 $188
🇺🇸 Chicago, United States
🇸🇪 Gothenburg, Sweden
Travel Between:

$429

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Mar - Mar 2026
💰 $214
🇺🇸 Chicago, United States
🇩🇰 Copenhagen, Denmark
Travel Between:

$796

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Mar - Mar 2026
💰 $398
🇺🇸 Chicago, United States
🇹🇭 Bangkok, Thailand
Travel Between:

$416

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Mar - Mar 2026
💰 $208
🇺🇸 Chicago, United States
🇸🇪 Gothenburg, Sweden
Travel Between:

$465

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Mar - Mar 2026
💰 $232
🇺🇸 Chicago, United States
🇨🇭 Zurich, Switzerland
Travel Between:

$860

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Apr - Apr 2025
💰 $430
🇺🇸 Chicago, United States
🇺🇬 Kampala, Uganda
Travel Between: