Cheap flights from Illinois to Caribbean

Travel > Caribbean

Looking for cheap flights to Caribbean? We have several useful tools to help you find the flight offer you are looking for. You can enter your search details into the box on the left and compare the current prices of our providers. You can also browse the table below containing the cheapest flights to Caribbean found by Travelgrove users for the next 6 months. Scrolling down you will find one more handy info box with the most recently found Caribbean flight offers. Check the page from top to bottom and pick the flight that suits you best!

Cheapest flights found for the next 6 months

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

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Check our newest flight offers to Caribbean:

  • $413US Airways flight US Airways 
    Chicago, IL (ORD)San Juan, PR (SJU)02/12/201506:07 am
    San Juan, PR (SJU)Chicago, IL (ORD)02/21/201506:45 am check price
  • $437American Airlines flight American Airlines 
    Chicago, IL (ORD)Trinidad, TT (POS)03/11/201506:35 am
    Trinidad, TT (POS)Chicago, IL (ORD)03/24/201502:30 pm check price
  • $463Air Canada flight Air Canada 
    Chicago, IL (ORD)Kingston, JM (KIN)02/01/201508:20 pm
    Kingston, JM (KIN)Chicago, IL (ORD)02/09/201501:40 pm check price
  • $491Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)Montego Bay, JM (MBJ)02/19/201505:30 pm
    Montego Bay, JM (MBJ)Chicago, IL (ORD)02/26/201501:20 pm check price
  • $506Aeromexico flight Aeromexico 
    Chicago, IL (ORD)San Salvador, SV (SAL)01/19/201512:10 am
    San Salvador, SV (SAL)Chicago, IL (ORD)02/03/201507:00 am check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesNew York City To Corpus Christi Multiple Airlines airfares from New York City in February
$398 Depart: 02/13/2015
Return: 02/16/2015

provided by FlightHub

Alaska AirlinesIndianapolis To Vancouver Alaska Airlines airfares from Indianapolis in December
$814 Depart: 12/26/2014
Return: 01/02/2015

provided by FareDepot

Multiple AirlinesPortland To New York City Multiple Airlines airfares from Portland in January
$378 Depart: 01/18/2015
Return: 01/25/2015

provided by FlightHub

US AirwaysChicago To Washington DC US Airways airfares from Chicago in January
$236 Depart: 01/07/2015
Return: 01/20/2015

provided by FlightHub

United AirlinesIndianapolis To Maui United Airlines airfares from Indianapolis in June
$1396 Depart: 06/07/2015
Return: 06/13/2015

provided by FareDepot

Qantas AirwaysDenver To Melbourne Qantas Airways airfares from Denver in January
$2545 Depart: 01/20/2015
Return: 01/28/2015

provided by FlightHub

Austrian AirlinesMiami To Tirana Austrian Airlines airfares from Miami in January
$1339 Depart: 01/14/2015
Return: 01/21/2015

provided by FlightHub

Spirit AirlinesPortland To Detroit Spirit Airlines airfares from Portland in January
$513 Depart: 01/09/2015
Return: 01/24/2015

provided by

United AirlinesLas Vegas To Toulouse United Airlines airfares from Las Vegas in April
$1396 Depart: 04/21/2015
Return: 04/28/2015

provided by FlightHub


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

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