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

Book your flight now with FlightHub and save!

Cheap San Juan airfares from $300/RT are provided by FlightHub. Outbound flight is leaving on 08/13/2014, 08:50 am from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 02:28 pm. The flight time is 5 hours and 38 minutes. The Returning flight departes on 09/03/2014, 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)08/13/201408:50 am
    San Juan, PR (SJU)Chicago, IL (ORD)09/03/201402:50 pm
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  • $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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  • $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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  • $328Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)09/03/201408:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)09/17/201408:16 am
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  • $329Major Us Carrier flight Major Us Carrier 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/29/201407:05 am
    San Juan, PR (SJU)Chicago, IL (ORD)10/03/201405:44 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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  • $141Major Us Carrier flight Major Us Carrier 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)08/29/201410:00 pm
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cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesNew York City To Tehran Multiple Airlines airfares from New York City in August
$2324 Depart: 08/06/2014
Return: 08/13/2014

provided by FareDepot

American AirlinesDetroit To San Juan American Airlines airfares from Detroit in August
$623 Depart: 08/09/2014
Return: 08/17/2014

provided by FlightHub

Air CanadaNew York City To Sapporo Air Canada airfares from New York City in August
$6128 Depart: 08/08/2014
Return: 08/21/2014

provided by FlightHub

United AirlinesMilwaukee To Boston United Airlines airfares from Milwaukee in September
$270 Depart: 09/12/2014
Return: 09/24/2014

provided by FareDepot

American AirlinesDallas To Roanoke American Airlines airfares from Dallas in November
$574 Depart: 11/05/2014
Return: 11/26/2014

provided by FareDepot

US AirwaysOrange County To Paris US Airways airfares from Orange County in September
$1392 Depart: 09/10/2014
Return: 09/22/2014

provided by FlightHub

Multiple AirlinesCalgary To San Francisco Multiple Airlines airfares from Calgary in August
$373 Depart: 08/30/2014
Return: 09/02/2014

provided by Faregeek

Multiple AirlinesLos Angeles To Amman Multiple Airlines airfares from Los Angeles in October
$941 Depart: 10/07/2014
Return: 10/22/2014

provided by Expedia

Multiple AirlinesLos Angeles To Calgary Multiple Airlines airfares from Los Angeles in September
$481 Depart: 09/13/2014
Return: 09/21/2014

provided by Expedia

 

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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