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Discover the Best Cheap Flight Deals from Chicago

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Recent deals from Chicago:

$118 to 🇺🇸 Denver, United States $147 to 🇺🇸 Las Vegas, United States $150 to 🇺🇸 West Palm Beach, United States See more deals from Chicago

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Latest cheap flight deals departing from Chicago.

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$118

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Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025
💰 $332
🇺🇸 Chicago, United States
🇺🇸 Denver, United States
Travel Between: 01 August 2025 To 06 August 2025

$147

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Sep - Sep 2025 / Aug - Aug 2025
💰 $278
🇺🇸 Chicago, United States
🇺🇸 Las Vegas, United States
Travel Between: 01 August 2025 To 06 August 2025

$150

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Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025 / Dec - Dec 2025 / Nov - Nov 2025
💰 $285
🇺🇸 Chicago, United States
🇺🇸 West Palm Beach, United States
Travel Between: 01 November 2025 To 06 November 2025

$159

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Sep - Sep 2025 / Aug - Aug 2025 / Jul - Jul 2025 / Nov - Nov 2025 / Oct - Oct 2025
💰 $186
🇺🇸 Chicago, United States
🇺🇸 Washington, United States
Travel Between: 01 July 2025 To 06 July 2025

$667

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Sep - Sep 2025
💰 $333
🇺🇸 Chicago, United States
🇮🇳 New Delhi, India
Travel Between:

$211

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Sep - Sep 2025
💰 $105
🇺🇸 Chicago, United States
🇬🇹 Guatemala City, Guatemala
Travel Between:

$579

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Nov - Nov 2025
💰 $289
🇺🇸 Chicago, United States
🇧🇷 Rio De Janeiro, Brazil
Travel Between:

$193

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Jun - Jun 2025
💰 $247
🇺🇸 Chicago, United States
🇺🇸 Newark, United States
Travel Between: 01 June 2025 To 06 June 2025

$451

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Nov - Nov 2025
💰 $225
🇺🇸 Chicago, United States
🇨🇿 Prague, Czechia
Travel Between:

$805

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Nov - Nov 2025
💰 $402
🇺🇸 Chicago, United States
🇵🇭 Manila, Philippines
Travel Between:

$398

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Oct - Oct 2025
💰 $199
🇺🇸 Chicago, United States
🇸🇪 Stockholm, Sweden
Travel Between:

$397

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Oct - Oct 2025
💰 $198
🇺🇸 Chicago, United States
🇳🇱 Amsterdam, Netherlands
Travel Between:

$337

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Aug - Sep 2025
💰 $168
🇺🇸 Chicago, United States
🇺🇸 Lihue, United States
Travel Between:

$357

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Jun - Jun 2025
💰 $323
🇺🇸 Chicago, United States
🇵🇷 San Juan, Puerto Rico
Travel Between: 01 June 2025 To 06 June 2025

$429

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Aug - Aug 2025
💰 $214
🇺🇸 Chicago, United States
🇮🇪 Dublin, Ireland
Travel Between:

$158

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Jun - Jun 2025 / Oct - Oct 2025 / Sep - Sep 2025 / Aug - Aug 2025 / Jul - Jul 2025 / Nov - Nov 2025
💰 $282
🇺🇸 Chicago, United States
🇺🇸 Newark, United States
Travel Between: 01 June 2025 To 06 June 2025

$193

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Jun - Jun 2025
💰 $267
🇺🇸 Chicago, United States
🇺🇸 Orlando, United States
Travel Between: 01 June 2025 To 06 June 2025

$200

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Jun - Jun 2025
💰 $140
🇺🇸 Chicago, United States
🇺🇸 Tampa, United States
Travel Between: 01 June 2025 To 06 June 2025

$465

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Nov - Nov 2025
💰 $232
🇺🇸 Chicago, United States
🇭🇺 Budapest, Hungary
Travel Between:

$446

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Jan - Jan 2026
💰 $223
🇺🇸 Chicago, United States
🇵🇹 Porto, Portugal
Travel Between:

$426

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Sep - Sep 2025
💰 $213
🇺🇸 Chicago, United States
🇪🇸 Barcelona, Spain
Travel Between:

$440

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Nov - Nov 2025
💰 $220
🇺🇸 Chicago, United States
🇵🇹 Lisbon, Portugal
Travel Between:

$77

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Sep - Sep 2025 / Aug - Aug 2025 / Jul - Jul 2025 / Jun - Jun 2025 / Nov - Nov 2025 / Oct - Oct 2025
💰 $183
🇺🇸 Chicago, United States
🇺🇸 Pittsburgh, United States
Travel Between: 01 June 2025 To 06 June 2025

$159

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Jun - Jun 2025
💰 $251
🇺🇸 Chicago, United States
🇺🇸 Baltimore, United States
Travel Between: 01 June 2025 To 06 June 2025