Cheap flights from Chicago to Caribbean

Travel > Caribbean

Travel tip: Visit Ponce on your holidays!

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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Travelgrove
 
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

Price overview for flights from Chicago to Caribbean

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

  • $489Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)08/22/202506:15 am
    Hamilton, BM (BDA)Chicago, IL (ORD)09/01/202511:44 am
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  • $625Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)08/26/202508:40 am
    Hamilton, BM (BDA)Chicago, IL (ORD)09/08/202501:48 pm
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  • $704Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)10/08/202506:50 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)10/14/202501:48 pm
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  • $2392Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)08/26/202508:35 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)09/08/202501:48 pm
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  • $2460Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)08/22/202508:35 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)09/01/202511:44 am
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  • $169Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aruba, AW (AUA)08/15/202508:12 pm
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  • $1342Westjet flight Westjet 
    FromToDepartureTime
    Chicago, IL (MDW)Aruba, AW (AUA)08/15/202512:43 pm
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