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 $238 / RT details

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Cheap St. Thomas Island airfares from $238/RT are provided by Cheapoair.com. Outbound flight is leaving on 01/21/2025, 03:22 pm from Chicago O`hare (ORD) airport and arrives at St Thomas Island Cyril King (STT) at 10:51 am. The flight time is 19 hours and 29 minutes. The Returning flight departes on 02/05/2025, 11:46 am (other return dates are also available). Date posted: 18 Nov 2024

Price evolution for flights From Chicago To Caribbean

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

• $238 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	St. Thomas Island, VI (STT)	01/21/2025	03:22 pm
  St. Thomas Island, VI (STT)	Chicago, IL (ORD)	02/05/2025	11:46 am

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• $253 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	01/03/2025	01:00 pm
  San Juan, PR (SJU)	Chicago, IL (ORD)	01/12/2025	10:09 pm

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• $256 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	03/08/2025	07:00 am
  San Juan, PR (SJU)	Chicago, IL (ORD)	03/16/2025	03:35 pm

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• $260 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	01/03/2025	06:40 am
  San Juan, PR (SJU)	Chicago, IL (ORD)	01/12/2025	09:49 pm

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• $274 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	St. Thomas Island, VI (STT)	01/29/2025	05:10 am
  St. Thomas Island, VI (STT)	Chicago, IL (ORD)	02/12/2025	11:35 am

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• $85 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	San Juan, PR (SJU)	12/10/2024	01:00 pm

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• $89 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	Aguadilla, PR (BQN)	12/09/2024	11:33 am

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• $150 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	St. Thomas Island, VI (STT)	12/06/2024	05:11 pm

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• $164 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	St. Thomas Island, VI (STT)	12/06/2024	05:11 pm

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• $166 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Kingston, JM (KIN)	12/07/2024	05:11 pm

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