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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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
cheapoair.com check priceFrom 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 - $625
Jetblue Airways
cheapoair.com check priceFrom 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 - $704
Jetblue Airways
cheapoair.com check priceFrom 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 - $2392
Multiple Airlines
cheapoair.com check priceFrom 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 - $2460
Multiple Airlines
cheapoair.com check priceFrom 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 - $169
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aruba, AW (AUA) 08/15/2025 08:12 pm - $1342
Westjet
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Aruba, AW (AUA) 08/15/2025 12:43 pm
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