Cheap flights from Illinois to Caribbean

Travel > Caribbean

Santiago has a long history. In 1541, the city was destroyed by native forces, which led to the Arauco War. In the 19th century, the city was a small town with few buildings.  The nitrate fertilizer in Northern Chile brought development in the country and promoted the capital city.... (read more in our Santiago Travel Guide)

Check current prices for flights to Caribbean at our partners' sites:

Search and Compare cheap Flights

Enter your travel details:Step 1

Select merchants to compare:Step 2

Cheapest flights found for the next 6 months

(click city name to see more / use right arrow to view later months)

Check our newest flight offers to Caribbean:

  • $328Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)San Juan, PR (SJU)10/06/201511:20 am
    San Juan, PR (SJU)Chicago, IL (ORD)10/20/201501:09 pm check price
  • $433Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)San Salvador, SV (SAL)09/23/201505:15 am
    San Salvador, SV (SAL)Chicago, IL (ORD)10/07/201501:20 am check price
  • $436American Airlines flight American Airlines 
    Chicago, IL (ORD)St. Croix Island, VI (STX)10/28/201506:10 am
    St. Croix Island, VI (STX)Chicago, IL (ORD)11/03/201505:05 pm check price
  • $446Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)St. Thomas Island, VI (STT)10/28/201510:55 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)11/04/201505:55 pm check price
  • $447Multiple Airlines flight Multiple Airlines 
    Chicago, IL (ORD)Nassau, BS (NAS)11/03/201504:30 pm
    Nassau, BS (NAS)Chicago, IL (ORD)11/06/201509:00 am check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesNewark To Tallinn Multiple Airlines airfares from Newark in July
$1362 Depart: 07/19/2015
Return: 07/27/2015

provided by FlightHub

Multiple AirlinesToronto To Hamburg Multiple Airlines airfares from Toronto in December
$985 Depart: 12/16/2015
Return: 01/01/2016

provided by FlightHub

United AirlinesLas Vegas To Saint Louis United Airlines airfares from Las Vegas in November
$372 Depart: 11/24/2015
Return: 12/02/2015

provided by FareDepot

Multiple AirlinesNew York City To Zagreb Multiple Airlines airfares from New York City in August
$1470 Depart: 08/02/2015
Return: 08/11/2015

provided by FareDepot

Qantas AirwaysAtlanta To Melbourne Qantas Airways airfares from Atlanta in April
$2173 Depart: 04/08/2015
Return: 04/28/2015

provided by FlightHub

Air CanadaSaskatoon To Toronto Air Canada airfares from Saskatoon in August
$538 Depart: 08/12/2015
Return: 08/19/2015

provided by

Multiple AirlinesMyrtle Beach To Newark Multiple Airlines airfares from Myrtle Beach in September
$810 Depart: 09/09/2015
Return: 09/23/2015

provided by FareDepot

Multiple AirlinesPhiladelphia To Thessaloniki Multiple Airlines airfares from Philadelphia in July
$5187 Depart: 07/15/2015
Return: 07/29/2015

provided by FlightHub

United AirlinesCarlsbad To Boston United Airlines airfares from Carlsbad in September
$531 Depart: 09/22/2015
Return: 10/13/2015

provided by FareDepot


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

more Caribbean travel deals

   Welcome to Travelgrove  register tell a friend bookmark it 
This airfare deal was found   ago. Click "Check price" to see current prices!