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:

  • $291Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)Port Au Prince, HT (PAP)03/11/201505:30 pm
    Port Au Prince, HT (PAP)Chicago, IL (ORD)03/17/201510:07 am check price
  • $347Multiple Airlines flight Multiple Airlines 
    Chicago, IL (ORD)San Juan, PR (SJU)08/06/201507:30 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/10/201504:40 pm check price
  • $441US Airways flight US Airways 
    Chicago, IL (ORD)Santo Domingo, DO (SDQ)06/02/201505:00 am
    Santo Domingo, DO (SDQ)Chicago, IL (ORD)06/09/201501:30 pm check price
  • $485Multiple Airlines flight Multiple Airlines 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)06/02/201507:30 am
    Punta Cana, DO (PUJ)Chicago, IL (ORD)06/09/201502:45 pm check price
  • $547United Airlines flight United Airlines 
    Chicago, IL (ORD)Aruba, AW (AUA)03/20/201505:00 am
    Aruba, AW (AUA)Chicago, IL (ORD)03/27/201503:04 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesBoston To Belize City Multiple Airlines airfares from Boston in July
$1601 Depart: 07/19/2015
Return: 08/02/2015

provided by FlightHub

Multiple AirlinesChicago To London Multiple Airlines airfares from Chicago in May
$875 Depart: 05/12/2015
Return: 06/08/2015

provided by Travelgrove

Multiple AirlinesSan Diego To Barcelona Multiple Airlines airfares from San Diego in June
$1723 Depart: 06/18/2015
Return: 07/05/2015

provided by FlightHub

US AirwaysAustin To Munich US Airways airfares from Austin in June
$1795 Depart: 06/11/2015
Return: 06/22/2015

provided by FlightHub

US AirwaysSarasota To Atlanta US Airways airfares from Sarasota in June
$530 Depart: 06/17/2015
Return: 07/08/2015

provided by Travelgrove

American AirlinesOakland To Paris American Airlines airfares from Oakland in April
$1464 Depart: 04/08/2015
Return: 04/19/2015

provided by FareDepot

Alaska AirlinesDetroit To Cabo San Lucas Alaska Airlines airfares from Detroit in March
$714 Depart: 03/11/2015
Return: 03/17/2015

provided by

United AirlinesColumbus To Fort Lauderdale United Airlines airfares from Columbus in April
$675 Depart: 04/03/2015
Return: 04/11/2015

provided by FlightHub

Sun Country AirlinesMinneapolis To San Francisco Sun Country Airlines airfares from Minneapolis in March
$427 Depart: 03/29/2015
Return: 04/03/2015

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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