Cheap flights from Chicago to Caribbean

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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 $169 / RT details

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Cheap San Juan airfares from $169/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/11/2025, 08:46 pm from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 02:27 am. The flight time is 5 hours and 41 minutes. The Returning flight departes on 03/19/2025, 03:05 am (other return dates are also available). Date posted: 06 Feb 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

  • $169Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)03/11/202508:46 pm
    San Juan, PR (SJU)Chicago, IL (ORD)03/19/202503:05 am
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  • $179Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)02/28/202507:18 pm
    San Juan, PR (SJU)Chicago, IL (ORD)03/12/202506:00 am
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  • $179Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)02/28/202504:44 pm
    San Juan, PR (SJU)Chicago, IL (ORD)03/12/202506:00 am
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  • $256Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)03/08/202507:00 am
    San Juan, PR (SJU)Chicago, IL (ORD)03/16/202503:35 pm
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  • $265Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)02/22/202503:14 pm
    St. Thomas Island, VI (STT)Chicago, IL (ORD)03/07/202512:11 pm
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  • $103Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)02/26/202507:18 pm
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  • $107Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)02/19/202507:10 am
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  • $113Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)02/21/202503:14 pm
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  • $130Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Saint Maarten, AN (SXM)03/03/202505:00 am
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  • $148Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Punta Cana, DO (PUJ)03/10/202507:42 pm
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