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 $237 / RT details

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Cheap St. Thomas Island airfares from $237/RT are provided by Cheapoair.com. Outbound flight is leaving on 05/20/2024, 06:40 pm from Chicago O`hare (ORD) airport and arrives at St Thomas Island Cyril King (STT) at 09:34 am. The flight time is 14 hours and 54 minutes. The Returning flight departes on 05/28/2024, 05:25 pm (other return dates are also available). Date posted: 17 Apr 2024

Price evolution for flights From Chicago To Caribbean

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

• $237 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	St. Thomas Island, VI (STT)	05/20/2024	06:40 pm
  St. Thomas Island, VI (STT)	Chicago, IL (ORD)	05/28/2024	05:25 pm

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• $257 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Punta Cana, DO (PUJ)	04/29/2024	05:00 am
  Punta Cana, DO (PUJ)	Chicago, IL (ORD)	05/08/2024	03:57 pm

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• $259 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	05/24/2024	11:10 am
  San Juan, PR (SJU)	Chicago, IL (ORD)	06/06/2024	06:09 am

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• $261 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Santo Domingo, DO (SDQ)	05/08/2024	06:40 pm
  Santo Domingo, DO (SDQ)	Chicago, IL (ORD)	05/16/2024	03:39 pm

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• $263 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Montego Bay, JM (MBJ)	04/29/2024	05:00 am
  Montego Bay, JM (MBJ)	Chicago, IL (ORD)	05/11/2024	12:45 pm

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• $74 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	San Juan, PR (SJU)	05/18/2024	05:45 pm

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• $84 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	San Juan, PR (SJU)	04/28/2024	02:44 pm

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• $85 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Punta Cana, DO (PUJ)	05/12/2024	05:47 am

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• $89 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Saint Maarten, AN (SXM)	04/28/2024	09:25 pm

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• $93 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	04/28/2024	09:24 am

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