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!

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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:

  • $347Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)St. Thomas Island, VI (STT)08/01/201605:15 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)08/15/201604:25 pm check price
  • $348Aeromexico flight Aeromexico 
    Chicago, IL (ORD)Santo Domingo, DO (SDQ)08/18/201607:00 am
    Santo Domingo, DO (SDQ)Chicago, IL (ORD)08/22/201608:41 am check price
  • $464Multiple Airlines flight Multiple Airlines 
    Chicago, IL (ORD)Hamilton, BM (BDA)11/15/201605:55 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)11/30/201601:09 pm check price
  • $482American Airlines flight American Airlines 
    Chicago, IL (ORD)St. Croix Island, VI (STX)08/09/201605:00 am
    St. Croix Island, VI (STX)Chicago, IL (ORD)08/15/201604:00 pm check price
  • $482Copa Air flight Copa Air 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)08/24/201609:00 am
    Punta Cana, DO (PUJ)Chicago, IL (ORD)08/30/201606:34 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Qatar AirwaysWashington DC To Kuala Lumpur Qatar Airways airfares from Washington DC in August
$2216 Depart: 08/01/2016
Return: 08/06/2016

provided by FlightHub

Multiple AirlinesSan Jose To Las Vegas Multiple Airlines airfares from San Jose in August
$662 Depart: 08/03/2016
Return: 08/10/2016

provided by Flightnetwork

Multiple AirlinesPhoenix To Midland Multiple Airlines airfares from Phoenix in June
$851 Depart: 06/28/2016
Return: 07/05/2016

provided by FareDepot

Multiple AirlinesHouston To Tunis Multiple Airlines airfares from Houston in July
$1498 Depart: 07/04/2016
Return: 08/04/2016

provided by FlightHub

Multiple AirlinesToronto To Hanoi Multiple Airlines airfares from Toronto in July
$1290 Depart: 07/27/2016
Return: 08/10/2016

provided by FlyFar

Jetblue AirwaysSeattle To Punta Cana Jetblue Airways airfares from Seattle in August
$848 Depart: 08/12/2016
Return: 08/25/2016

provided by FlightHub

United AirlinesPhiladelphia To Ottawa United Airlines airfares from Philadelphia in August
$706 Depart: 08/15/2016
Return: 08/21/2016

provided by FareDepot

AeromexicoAtlanta To Vancouver Aeromexico airfares from Atlanta in August
$2188 Depart: 08/01/2016
Return: 08/08/2016

provided by Flightnetwork

Royal Jordanian AirlinesChicago To Dubai Royal Jordanian Airlines airfares from Chicago in September
$711 Depart: 09/27/2016
Return: 10/12/2016

provided by


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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