Cheap flights from Chicago to Caribbean

Travel > Caribbean

Travel tip: San Juan boasts numerous museums, hotels, historical buildings, beaches, restaurants and shopping centers. In San Juan there are a lot of attractions, for example: Ocean Park, Old San Juan, Isla Verde and Condado

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 $300 / RT details

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Cheap San Juan airfares from $300/RT are provided by FlightHub. Outbound flight is leaving on 09/03/2014, 09:00 am from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 02:41 pm. The flight time is 5 hours and 41 minutes. The Returning flight departes on 09/17/2014, 02:50 pm (other return dates are also available). Date posted: 09 Jul 2014

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

  • $300Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)09/03/201409:00 am
    San Juan, PR (SJU)Chicago, IL (ORD)09/17/201402:50 pm
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  • $305Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)11/04/201405:10 am
    San Juan, PR (SJU)Chicago, IL (ORD)11/18/201403:40 pm
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  • $306Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)11/04/201409:05 am
    San Juan, PR (SJU)Chicago, IL (ORD)11/18/201403:40 pm
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  • $310Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)10/03/201405:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)10/11/201404:25 pm
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  • $325United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/29/201408:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)10/03/201402:50 pm
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  • $137Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)08/22/201405:50 am
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  • $137Major Us Carrier flight Major Us Carrier 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)08/22/201406:55 pm
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  • $139Us Airways flight Us Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)08/29/201410:00 pm
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  • $139American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)08/22/201410:00 pm
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  • $140Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/26/201405:15 am
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Recently found cheap flight deals

Multiple AirlinesLos Angeles To Bucharest Multiple Airlines airfares from Los Angeles in September
$883 Depart: 09/15/2014
Return: 10/14/2014

provided by Travelgrove

United AirlinesBeaumont To Orlando United Airlines airfares from Beaumont in December
$480 Depart: 12/13/2014
Return: 12/20/2014

provided by FlightHub

Multiple AirlinesDenver To Edinburgh Multiple Airlines airfares from Denver in October
$1267 Depart: 10/08/2014
Return: 10/21/2014

provided by Cheapoair.com

US AirwaysAtlanta To Tampa US Airways airfares from Atlanta in December
$553 Depart: 12/27/2014
Return: 01/03/2015

provided by FlightHub

Multiple AirlinesPhiladelphia To Rome Multiple Airlines airfares from Philadelphia in March
$1255 Depart: 03/15/2015
Return: 04/09/2015

provided by Cheapoair.com

Multiple AirlinesSalt Lake City To Paris Multiple Airlines airfares from Salt Lake City in April
$1324 Depart: 04/17/2015
Return: 05/01/2015

provided by Travelgrove

Spirit AirlinesDenver To Los Angeles Spirit Airlines airfares from Denver in November
$206 Depart: 11/06/2014
Return: 11/13/2014

provided by Travelgrove

Multiple AirlinesTampa To Vancouver Multiple Airlines airfares from Tampa in August
$723 Depart: 08/29/2014
Return: 09/01/2014

provided by FlightHub

Multiple AirlinesNew York City To Mashad Multiple Airlines airfares from New York City in September
$3744 Depart: 09/23/2014
Return: 10/08/2014

provided by FlightHub

 

Specify your search details. Browse the cheapest flights from Chicago to Caribbean, Caribbean hotel rooms and Chicago to Caribbean vacation packages from the most popular providers, airline consolidators and travel search engines.

Know what to do when flying to Caribbean?

San Juan Travel Guide Located in the Caribbean, in the Northern Coastal Plains of the island Puerto Rico, San Juan is the capital of this island. Known as "La Ciudad Amurallada" (the walled city), San Juan is an important port and also the oldest city in [...]
San Juan History San Juan, also known as “La Ciudad Amurallada”, occupies a land of 122 square kilometer and houses 442,447 inhabitants. The city is positioned in the Northern Coastal Plains and lying under the Karsts zone to the north of Caguas and [...]
San Juan Sightseeing Once you set foot on the soil of San Juan, you will feel as if you were taken back 500 years ago in 1508. In this city, you will experience firsthand what Latin American culture really is like. Though covered by a wall, San Juan never fails to [...]
San Juan Nightlife Like most cities, the San Juan night scene also comes alive during the weekends. Clubs, bars, discos and a lot more are to be found here. Whatever your action is, there is surely something for you in San Juan.  The majority of those who go out [...]
San Juan Pictures
  • El Morro - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • El Morro - San Juanview

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