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 $299 / RT details

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Cheap San Juan airfares from $299/RT are provided by Faregeek. Outbound flight is leaving on 08/07/2014, 08:15 am from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 02:05 pm. The flight time is 5 hours and 50 minutes. The Returning flight departes on 08/12/2014, 03:05 pm (other return dates are also available). Date posted: 03 Apr 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

  • $299American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/07/201408:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/12/201403:05 pm
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  • $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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  • $319Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/07/201408:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/12/201402:55 pm
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  • $320American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/07/201408:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/12/201403:05 pm
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  • $159Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)08/25/201405:07 pm
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  • $159Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)08/25/201405:07 pm
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  • $166American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/12/201408:15 am
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  • $166American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/12/201408:15 am
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  • $166United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/12/201408:10 am
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Recently found cheap flight deals

American AirlinesAtlanta To Sao Paulo American Airlines airfares from Atlanta in July
$1419 Depart: 07/22/2014
Return: 08/05/2014

provided by FlightHub

Multiple AirlinesDenver To Philadelphia Multiple Airlines airfares from Denver in November
$415 Depart: 11/25/2014
Return: 11/30/2014

provided by FlightHub

British AirwaysDallas To Prague British Airways airfares from Dallas in April
$1027 Depart: 04/30/2014
Return: 05/13/2014

provided by Cheapoair.com

Multiple AirlinesHonolulu To Saipan Multiple Airlines airfares from Honolulu in October
$2218 Depart: 10/28/2014
Return: 11/04/2014

provided by FlightHub

American AirlinesHouston To Cancun American Airlines airfares from Houston in July
$542 Depart: 07/26/2014
Return: 08/02/2014

provided by Faregeek

Multiple AirlinesLos Angeles To Guadalajara Multiple Airlines airfares from Los Angeles in August
$409 Depart: 08/21/2014
Return: 08/24/2014

provided by FlightHub

KLM Royal Dutch AirlinesManchester, NH To Rome KLM Royal Dutch Airlines airfares from Manchester, NH in August
$1713 Depart: 08/08/2014
Return: 08/16/2014

provided by FareDepot

Multiple AirlinesWashington DC To Port Louis Multiple Airlines airfares from Washington DC in August
$3443 Depart: 08/06/2014
Return: 08/12/2014

provided by FlightHub

United AirlinesToronto To Tucson United Airlines airfares from Toronto in October
$732 Depart: 10/16/2014
Return: 10/21/2014

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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