Cheap flights from Illinois to Caribbean

Travel > Caribbean

In addition to these historical landmarks are the beautiful coastlines that are perfect for families. After an educational tour around the city, you take a walk along the shore and enjoy the heat of the tropical sun. What else could be better than that? Whenever you feel like bringing home some souvenirs for the ones you left at home, head right to the cruise ship docks and along Calle San Francisco to purchase local island crafts. On Calle Marina the residents of San Juan present you with a... (read more in our San Juan Sightseeing)

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  • $299American Airlines flight American Airlines 
    Chicago, IL (ORD)San Juan, PR (SJU)08/07/201408:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/12/201403:05 pm check price
  • $420Delta Airlines flight Delta Airlines 
    Chicago, IL (ORD)Hamilton, BM (BDA)06/06/201406:00 am
    Hamilton, BM (BDA)Chicago, IL (ORD)06/13/201409:00 am check price
  • $455United Airlines flight United Airlines 
    Chicago, IL (ORD)Aguadilla, PR (BQN)05/15/201402:15 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)05/30/201402:00 am check price
  • $458American Airlines flight American Airlines 
    Chicago, IL (ORD)St. Croix Island, VI (STX)05/29/201405:30 am
    St. Croix Island, VI (STX)Chicago, IL (ORD)06/02/201402:20 pm check price
  • $463Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)St. Thomas Island, VI (STT)05/29/201409:00 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)06/02/201405:00 pm check price
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Recently found cheap flight deals

Multiple AirlinesAtlantic City To San Juan Multiple Airlines airfares from Atlantic City in May
$792 Depart: 05/28/2014
Return: 06/10/2014

provided by Travelgrove

Air CanadaHalifax To Ottawa Air Canada airfares from Halifax in May
$433 Depart: 05/10/2014
Return: 05/17/2014

provided by

Multiple AirlinesPhoenix To Berlin Multiple Airlines airfares from Phoenix in December
$1498 Depart: 12/21/2014
Return: 12/28/2014

provided by FlightHub

Malaysian AirlinesDallas To Kuala Lumpur Malaysian Airlines airfares from Dallas in May
$1951 Depart: 05/23/2014
Return: 05/31/2014

provided by Expedia

Multiple AirlinesPhoenix To Eugene Multiple Airlines airfares from Phoenix in July
$368 Depart: 07/16/2014
Return: 07/30/2014

provided by FlightHub

Emirates AirlinesDallas To Jeddah Emirates Airlines airfares from Dallas in May
$1482 Depart: 05/21/2014
Return: 05/26/2014

provided by FlightHub

United AirlinesSyracuse To Chicago United Airlines airfares from Syracuse in May
$338 Depart: 05/06/2014
Return: 05/12/2014

provided by FareDepot

Multiple AirlinesProvidence To London Multiple Airlines airfares from Providence in June
$5375 Depart: 06/02/2014
Return: 06/09/2014

provided by FlightHub

Delta AirlinesLittle Rock To Fayetteville Delta Airlines airfares from Little Rock in May
$822 Depart: 05/19/2014
Return: 05/29/2014

provided by FlightHub


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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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