Cheap flights from Illinois to Caribbean

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The city of Bridgetown was established in 1628, when a group of British sailors led by the Earl of Carlisle set up a community by the Constitution River. However, the history of Bridgetown region can be traced back to around 350 B.C. when the first wave of nomadic groups arrived in the island; the people belonged to the Saladoid-Barrancoid group. The Arawak people arrived around 900 B.C. These two South American groups co-habited in the island for a pretty long time until they were driven... (read more in our Bridgetown History)

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Check our newest flight offers to Caribbean:

  • $274Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)San Juan, PR (SJU)10/17/201611:55 am
    San Juan, PR (SJU)Chicago, IL (ORD)10/27/201612:40 pm check price
  • $362American Airlines flight American Airlines 
    Chicago, IL (ORD)Belize City, BZ (BZE)10/16/201606:00 am
    Belize City, BZ (BZE)Chicago, IL (ORD)10/29/201602:20 pm check price
  • $375Frontier Airlines flight Frontier Airlines 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)12/11/201607:29 am
    Punta Cana, DO (PUJ)Chicago, IL (ORD)12/15/201603:20 pm check price
  • $394Southwest Airlines flight Southwest Airlines 
    Chicago, IL (MDW)Nassau, BS (NAS)11/09/201606:15 am
    Nassau, BS (NAS)Chicago, IL (MDW)11/23/201602:25 pm check price
  • $407Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)Montego Bay, JM (MBJ)09/30/201605:15 am
    Montego Bay, JM (MBJ)Chicago, IL (ORD)10/07/201602:58 pm check price
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Southwest AirlinesLos Angeles To Sacramento Southwest Airlines airfares from Los Angeles in September
$179 Depart: 09/01/2016
Return: 09/05/2016

provided by Flightnetwork

LufthansaLos Angeles To Amman Lufthansa airfares from Los Angeles in November
$929 Depart: 11/30/2016
Return: 12/06/2016

provided by

Multiple AirlinesWashington DC To Providence Multiple Airlines airfares from Washington DC in September
$201 Depart: 09/28/2016
Return: 10/12/2016

provided by FareDepot

Alaska AirlinesChicago To Reno Alaska Airlines airfares from Chicago in September
$505 Depart: 09/07/2016
Return: 09/18/2016

provided by FareDepot

Southwest AirlinesManchester, NH To Tampa Southwest Airlines airfares from Manchester, NH in November
$358 Depart: 11/04/2016
Return: 11/08/2016

provided by Flightnetwork

British AirwaysToronto To Basel British Airways airfares from Toronto in October
$986 Depart: 10/01/2016
Return: 10/09/2016

provided by FlightHub

United AirlinesOrlando To Houston United Airlines airfares from Orlando in November
$373 Depart: 11/22/2016
Return: 11/29/2016

provided by FlightHub

American AirlinesPhiladelphia To Saint Thomas American Airlines airfares from Philadelphia in November
$872 Depart: 11/05/2016
Return: 11/12/2016

provided by FlightHub

Multiple AirlinesSan Jose To Kansas City Multiple Airlines airfares from San Jose in January
$443 Depart: 01/04/2017
Return: 01/18/2017

provided by FareDepot


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  • San Juan, Puerto Rico - San Juanview
  • San Juan, Puerto Rico - San Juanview
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