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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$432 to 🇪🇸 Madrid, Spain $417 to 🇸🇪 Stockholm, Sweden $416 to 🇮🇹 Milan, Italy 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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$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:

$975

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Oct - Oct 2025
💰 $139
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between: 13 October 2025 To 15 October 2025

$671

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Oct - Oct 2025
💰 $327
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between: 13 October 2025 To 19 October 2025

$692

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Oct - Oct 2025
💰 $389
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between: 09 October 2025 To 12 October 2025

$496

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

$490

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Sep - Sep 2025
💰 $302
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between: 07 September 2025 To 11 September 2025

$899

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Sep - Sep 2025
💰 $2,203
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between: 17 September 2025 To 19 September 2025

$550

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Sep - Sep 2025
💰 $242
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between: 05 September 2025 To 11 September 2025

$683

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Sep - Sep 2025
💰 $151
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between: 01 September 2025 To 04 September 2025

$581

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Aug - Sep 2025
💰 $253
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between: 29 August 2025 To 04 September 2025

$691

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Aug - Sep 2025
💰 $234
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between: 31 August 2025 To 04 September 2025

$614

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Sep - Sep 2025
💰 $283
🇺🇸 Chicago, United States
🇫🇷 Paris, France
Travel Between: 07 September 2025 To 11 September 2025

$623

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Sep - Sep 2025
💰 $365
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between: 16 September 2025 To 25 September 2025

$728

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Sep - Sep 2025
💰 $535
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between: 14 September 2025 To 19 September 2025

$1,099

View Deal
Sep - Sep 2025
💰 $241
🇺🇸 Chicago, United States
🇲🇾 Kuala Lumpur, Malaysia
Travel Between: 12 September 2025 To 23 September 2025

$784

View Deal
Sep - Sep 2025
💰 $506
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between: 15 September 2025 To 19 September 2025

$481

View Deal
Aug - Aug 2025
💰 $256
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between: 25 August 2025 To 29 August 2025