Cheap flights from Illinois to Caribbean

Travel > Caribbean

Santiago has something to offer to all. You can’t be get bored or feel lonely in the warm and friendly atmosphere of Santiago. Santiago also provides a great shopping experience to the natives and foreign visitors.  Some of the best shopping avenues in the city are Providencia Avenue, Patio Bellavista mall and Swank Bellavista area.... (read more in our Santiago Nightlife)

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Cheapest flights found for the next 6 months

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Check our newest flight offers to Caribbean:

  • $303Multiple Airlines flight Multiple Airlines 
    Chicago, IL (ORD)San Juan, PR (SJU)03/12/201610:13 pm
    San Juan, PR (SJU)Chicago, IL (ORD)03/17/201601:50 pm check price
  • $391Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)Port Au Prince, HT (PAP)09/09/201507:00 pm
    Port Au Prince, HT (PAP)Chicago, IL (ORD)09/18/201510:10 am check price
  • $468Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Ponce, PR (PSE)03/12/201605:51 pm
    Ponce, PR (PSE)Chicago, IL (ORD)03/17/201605:00 am check price
  • $473United Airlines flight United Airlines 
    Chicago, IL (ORD)Santo Domingo, DO (SDQ)10/31/201508:55 pm
    Santo Domingo, DO (SDQ)Chicago, IL (ORD)11/07/201506:00 am check price
  • $477American Airlines flight American Airlines 
    Chicago, IL (ORD)Santiago, DO (STI)09/13/201501:20 pm
    Santiago, DO (STI)Chicago, IL (ORD)09/18/201508:45 am check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesGrand Rapids To Richmond Multiple Airlines airfares from Grand Rapids in October
$710 Depart: 10/04/2015
Return: 10/18/2015

provided by FlightHub

Lan AirlinesToronto To Havana Lan Airlines airfares from Toronto in November
$2153 Depart: 11/06/2015
Return: 11/14/2015

provided by FlightHub

Emirates AirlinesWashington DC To Islamabad Emirates Airlines airfares from Washington DC in September
$1272 Depart: 09/09/2015
Return: 09/15/2015

provided by FlightHub

Brussels AirlinesBoston To Basel Brussels Airlines airfares from Boston in September
$1408 Depart: 09/01/2015
Return: 01/01/2016

provided by FlightHub

Multiple AirlinesFort Myers To Boston Multiple Airlines airfares from Fort Myers in September
$300 Depart: 09/12/2015
Return: 09/27/2015

provided by

Multiple AirlinesAtlanta To Port Louis Multiple Airlines airfares from Atlanta in November
$5167 Depart: 11/04/2015
Return: 11/17/2015

provided by Tripsta

United AirlinesFort Lauderdale To Portland United Airlines airfares from Fort Lauderdale in October
$312 Depart: 10/13/2015
Return: 10/27/2015

provided by Tripsta

Multiple AirlinesWashington DC To Shannon Multiple Airlines airfares from Washington DC in October
$1061 Depart: 10/27/2015
Return: 11/04/2015

provided by FareDepot

Multiple AirlinesVictoria To Seattle Multiple Airlines airfares from Victoria in September
$439 Depart: 09/16/2015
Return: 09/23/2015

provided by Tripsta


Specify your search details. Browse the cheapest flights from Illinois to Caribbean, Caribbean hotel rooms and Illinois to Caribbean vacation packages from the most popular providers, airline consolidators and travel search engines.

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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