Cheap flights from Illinois to Caribbean

Travel > Caribbean

Though covered by a wall, San Juan never fails to reach out to its neighboring towns and even to other parts of the world. It has proven to be one of the most sought-after tourist destinations in Puerto Rico. There is a variety of sights to see in this 500-year-old city.... (read more in our San Juan Sightseeing)

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Cheapest flights found for the next 6 months

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Check our newest flight offers to Caribbean:

  • $332US Airways flight US Airways 
    Chicago, IL (ORD)San Juan, PR (SJU)11/06/201506:10 am
    San Juan, PR (SJU)Chicago, IL (ORD)11/14/201505:40 pm check price
  • $355Major Carrier flight Major Carrier 
    Chicago, IL (ORD)St. Thomas Island, VI (STT)05/13/201507:10 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)05/19/201503:59 pm check price
  • $425American Airlines flight American Airlines 
    Chicago, IL (ORD)St. Croix Island, VI (STX)05/13/201507:27 am
    St. Croix Island, VI (STX)Chicago, IL (ORD)05/19/201504:05 pm check price
  • $453American Airlines flight American Airlines 
    Chicago, IL (ORD)Saint Maarten, AN (SXM)04/22/201508:45 am
    Saint Maarten, AN (SXM)Chicago, IL (ORD)04/29/201508:00 am check price
  • $488Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)Santo Domingo, DO (SDQ)06/09/201507:10 am
    Santo Domingo, DO (SDQ)Chicago, IL (ORD)06/15/201503:03 pm check price
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Recently found cheap flight deals

Multiple AirlinesDallas To Midland/Odessa Multiple Airlines airfares from Dallas in March
$257 Depart: 03/24/2015
Return: 04/08/2015

provided by FareDepot

Multiple AirlinesEdmonton To New York City Multiple Airlines airfares from Edmonton in March
$496 Depart: 03/24/2015
Return: 04/08/2015

provided by Travelgrove

US AirwaysSan Francisco To Hartford US Airways airfares from San Francisco in March
$759 Depart: 03/11/2015
Return: 03/31/2015

provided by FlightHub

US AirwaysNewark To Baltimore US Airways airfares from Newark in March
$370 Depart: 03/25/2015
Return: 04/08/2015

provided by FlightHub

Lan AirlinesDallas To Belem Lan Airlines airfares from Dallas in December
$1322 Depart: 12/30/2014
Return: 01/14/2015

provided by FlightHub

Multiple AirlinesGreensboro To Fort Lauderdale Multiple Airlines airfares from Greensboro in March
$534 Depart: 03/21/2015
Return: 03/29/2015

provided by Travelgrove

British AirwaysAtlanta To Manchester British Airways airfares from Atlanta in September
$1303 Depart: 09/03/2014
Return: 09/24/2014

provided by

Virgin AmericaSeattle To Boston Virgin America airfares from Seattle in May
$449 Depart: 05/01/2015
Return: 05/10/2015

provided by

Air CanadaLas Vegas To Hong Kong Air Canada airfares from Las Vegas in March
$1160 Depart: 03/18/2015
Return: 03/31/2015

provided by


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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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