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 $489 / RT details

Book your flight now with Cheapoair.com and save!

Cheap Hamilton airfares from $489/RT are provided by Cheapoair.com. Outbound flight is leaving on 08/22/2025, 06:15 am from Chicago O`hare (ORD) airport and arrives at Bermuda Kindley (BDA) at 12:46 pm. The flight time is 6 hours and 31 minutes. The Returning flight departes on 09/01/2025, 11:44 am (other return dates are also available). Date posted: 30 Jun 2025

Price evolution for flights From Chicago To Caribbean

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

• $489 Jetblue Airways 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	08/22/2025	06:15 am
  Hamilton, BM (BDA)	Chicago, IL (ORD)	09/01/2025	11:44 am

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• $625 Jetblue Airways 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	08/26/2025	08:40 am
  Hamilton, BM (BDA)	Chicago, IL (ORD)	09/08/2025	01:48 pm

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• $704 Jetblue Airways 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	10/08/2025	06:50 pm
  Hamilton, BM (BDA)	Chicago, IL (ORD)	10/14/2025	01:48 pm

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• $2392 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	08/26/2025	08:35 pm
  Hamilton, BM (BDA)	Chicago, IL (ORD)	09/08/2025	01:48 pm

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• $2460 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Hamilton, BM (BDA)	08/22/2025	08:35 pm
  Hamilton, BM (BDA)	Chicago, IL (ORD)	09/01/2025	11:44 am

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• $169 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Aruba, AW (AUA)	08/15/2025	08:12 pm

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• $1342 Westjet 

  From	To	Departure	Time
  Chicago, IL (MDW)	Aruba, AW (AUA)	08/15/2025	12:43 pm

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