Cheap flights from Illinois to Caribbean

Travel > Caribbean

The best time to visit it is off the hot season from May to October as the temperatures can become unbearable by those not used to heat mainly due to the high humidity in the air. The hot season is also the period when most of the hurricanes occur so it is better to avoid this period. It does not mean that you should exclude the possibility to come here because of the hurricane danger. Natural phenomena can happen anywhere any time.... (read more in our Punta Cana Travel Guide)

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Cheapest flights found for the next 6 months

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Check our newest flight offers to Caribbean:

  • $328Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)San Juan, PR (SJU)04/17/201605:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)05/01/201604:15 pm check price
  • $380Delta Airlines flight Delta Airlines 
    Chicago, IL (ORD)St. Thomas Island, VI (STT)03/21/201605:45 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)03/28/201603:35 pm check price
  • $407United Airlines flight United Airlines 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)02/16/201609:40 am
    Punta Cana, DO (PUJ)Chicago, IL (ORD)02/23/201602:06 pm check price
  • $462Aeromexico flight Aeromexico 
    Chicago, IL (ORD)Santo Domingo, DO (SDQ)05/26/201603:10 pm
    Santo Domingo, DO (SDQ)Chicago, IL (ORD)06/05/201608:00 am check price
  • $469Aeromexico flight Aeromexico 
    Chicago, IL (ORD)San Salvador, SV (SAL)03/20/201604:09 pm
    San Salvador, SV (SAL)Chicago, IL (ORD)04/03/201612:48 pm check price
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Recently found cheap flight deals

Jetblue AirwaysDurham To Chicago Jetblue Airways airfares from Durham in March
$538 Depart: 03/20/2016
Return: 04/03/2016

provided by FlightHub

Multiple AirlinesOrange County To Buffalo Multiple Airlines airfares from Orange County in June
$578 Depart: 06/01/2016
Return: 06/08/2016

provided by FareDepot

Multiple AirlinesManchester To Fort Myers Multiple Airlines airfares from Manchester in March
$720 Depart: 03/12/2016
Return: 03/19/2016

provided by Flightnetwork

SAS Scandinavian AirlinesChicago To Munich SAS Scandinavian Airlines airfares from Chicago in March
$1126 Depart: 03/05/2016
Return: 03/18/2016

provided by FlightHub

Major US CarrierLos Angeles To Port Au Prince Major US Carrier airfares from Los Angeles in February
$687 Depart: 02/21/2016
Return: 03/06/2016

provided by FareDepot

Multiple AirlinesDallas To Doha Multiple Airlines airfares from Dallas in February
$1258 Depart: 02/16/2016
Return: 03/02/2016

provided by FlightHub

United AirlinesSan Jose To Orange County United Airlines airfares from San Jose in April
$531 Depart: 04/27/2016
Return: 05/11/2016

provided by FareDepot

Avianca AirlinesToronto To Panama City Avianca Airlines airfares from Toronto in March
$687 Depart: 03/22/2016
Return: 04/04/2016

provided by

Multiple AirlinesSan Diego To Barcelona Multiple Airlines airfares from San Diego in July
$5412 Depart: 07/25/2016
Return: 08/06/2016

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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