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 $685 / RT details

Book your flight now with Cheapoair.com and save!

Cheap Montego Bay airfares from $685/RT are provided by Cheapoair.com. Outbound flight is leaving on 05/13/2025, 05:05 am from Chicago O`hare (ORD) airport and arrives at Montego Bay Sangster (MBJ) at 11:41 am. The flight time is 6 hours and 36 minutes. The Returning flight departes on 05/28/2025, 03:33 pm (other return dates are also available). Date posted: 14 Jan 2025

Price evolution for flights From Chicago To Caribbean

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

• $685 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Montego Bay, JM (MBJ)	05/13/2025	05:05 am
  Montego Bay, JM (MBJ)	Chicago, IL (ORD)	05/28/2025	03:33 pm

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• $886 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	Aguadilla, PR (BQN)	04/19/2025	12:58 pm
  Aguadilla, PR (BQN)	Chicago, IL (MDW)	04/27/2025	02:47 am

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• $1857 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	04/22/2025	10:20 pm
  Hamilton, BM (BDA)	Chicago, IL (ORD)	05/06/2025	07:50 pm

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• $2351 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	06/10/2025	10:20 pm
  Hamilton, BM (BDA)	Chicago, IL (ORD)	06/24/2025	07:50 pm

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• $2710 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	07/02/2025	10:25 pm
  Hamilton, BM (BDA)	Chicago, IL (ORD)	07/15/2025	07:50 pm

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• $125 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	St. Thomas Island, VI (STT)	04/17/2025	07:49 pm

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• $1485 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	06/24/2025	10:25 pm

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• $1709 British Airways 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	04/23/2025	08:35 pm

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• $1717 British Airways 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	04/16/2025	08:30 pm

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• $2974 British Airways 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	06/24/2025	10:25 pm

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