Cheap flights from Chicago to Caribbean

Travel > Caribbean

Check our current prices for flights from Chicago to Caribbean. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Chicago to Caribbean, you will need to run a search below.

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From $183 / RT details

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Cheap San Juan airfares from $183/RT are provided by Cheapoair.com. Outbound flight is leaving on 10/08/2024, 05:05 am from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 07:08 pm. The flight time is 14 hours and 3 minutes. The Returning flight departes on 10/16/2024, 08:59 pm (other return dates are also available). Date posted: 26 Jun 2024

Price evolution for flights From Chicago To Caribbean

Recent Deals on Flights from Chicago to Caribbean:Roundtrip / Oneway

• $183 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	10/08/2024	05:05 am
  San Juan, PR (SJU)	Chicago, IL (ORD)	10/16/2024	08:59 pm

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• $187 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	09/25/2024	05:55 pm
  San Juan, PR (SJU)	Chicago, IL (ORD)	10/08/2024	07:54 pm

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• $209 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	10/08/2024	05:05 am
  San Juan, PR (SJU)	Chicago, IL (ORD)	10/16/2024	10:50 am

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• $211 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	09/25/2024	11:37 am
  San Juan, PR (SJU)	Chicago, IL (ORD)	10/08/2024	07:54 pm

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• $229 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	St. Thomas Island, VI (STT)	08/28/2024	08:30 am
  St. Thomas Island, VI (STT)	Chicago, IL (ORD)	09/05/2024	10:35 am

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• $71 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Saint Maarten, AN (SXM)	08/09/2024	05:57 pm

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• $81 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Port Au Prince, HT (PAP)	08/13/2024	06:46 pm

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• $82 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	08/13/2024	10:16 am

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• $83 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	08/08/2024	05:42 pm

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• $84 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	Saint Maarten, AN (SXM)	08/09/2024	06:11 pm

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