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:

  • $344Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)San Juan, PR (SJU)08/19/201508:54 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/26/201503:34 pm check price
  • $358Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)Aguadilla, PR (BQN)08/19/201506:10 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)09/01/201503:04 am check price
  • $359United Airlines flight United Airlines 
    Chicago, IL (ORD)Manzanillo, MX (ZLO)05/05/201505:15 am
    Manzanillo, MX (ZLO)Chicago, IL (ORD)05/21/201508:40 am check price
  • $381Delta Airlines flight Delta Airlines 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)05/03/201506:30 am
    Punta Cana, DO (PUJ)Chicago, IL (ORD)05/07/201502:55 pm check price
  • $425US Airways flight US Airways 
    Chicago, IL (ORD)Trinidad, TT (POS)05/10/201505:00 am
    Trinidad, TT (POS)Chicago, IL (ORD)05/22/201506:45 am check price
cheap domestic and international flights

Recently found cheap flight deals

Frontier AirlinesTampa To Miami Frontier Airlines airfares from Tampa in May
$1421 Depart: 05/07/2015
Return: 05/10/2015

provided by FareDepot

US AirwaysBirmingham To Saint Thomas US Airways airfares from Birmingham in May
$1069 Depart: 05/23/2015
Return: 05/30/2015

provided by FlightHub

Multiple AirlinesPhoenix To Appleton Multiple Airlines airfares from Phoenix in June
$684 Depart: 06/01/2015
Return: 06/06/2015

provided by Tripsta

British AirwaysBaltimore To Dublin British Airways airfares from Baltimore in June
$1409 Depart: 06/26/2015
Return: 07/09/2015

provided by

US AirwaysPhiladelphia To Charleston US Airways airfares from Philadelphia in June
$475 Depart: 06/14/2015
Return: 06/20/2015

provided by FlightHub

Multiple AirlinesSan Francisco To Pago Pago Multiple Airlines airfares from San Francisco in June
$1781 Depart: 06/07/2015
Return: 06/19/2015

provided by

US AirwaysNew York City To Chattanooga US Airways airfares from New York City in July
$319 Depart: 07/02/2015
Return: 07/05/2015

provided by FlightHub

US AirwaysMaui To Portland US Airways airfares from Maui in September
$737 Depart: 09/05/2015
Return: 09/12/2015

provided by FlightHub

Multiple AirlinesCharlotte To Cincinnati Multiple Airlines airfares from Charlotte in June
$365 Depart: 06/09/2015
Return: 06/16/2015

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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