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:

  • $344US Airways flight US Airways 
    Chicago, IL (ORD)San Juan, PR (SJU)01/01/201502:55 pm
    San Juan, PR (SJU)Chicago, IL (ORD)01/11/201508:44 pm check price
  • $454US Airways flight US Airways 
    Chicago, IL (ORD)Nassau, BS (NAS)02/11/201507:25 am
    Nassau, BS (NAS)Chicago, IL (ORD)02/15/201510:20 am check price
  • $483American Airlines flight American Airlines 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)04/15/201507:30 am
    Punta Cana, DO (PUJ)Chicago, IL (ORD)04/23/201502:34 pm check price
  • $493Air Canada flight Air Canada 
    Chicago, IL (ORD)Bridgetown, BB (BGI)01/20/201508:20 pm
    Bridgetown, BB (BGI)Chicago, IL (ORD)01/28/201505:20 pm check price
  • $533Multiple Airlines flight Multiple Airlines 
    Chicago, IL (ORD)St. Thomas Island, VI (STT)04/04/201506:55 pm
    St. Thomas Island, VI (STT)Chicago, IL (ORD)04/11/201505:10 pm check price
cheap domestic and international flights

Recently found cheap flight deals

American AirlinesLos Angeles To Charleston, WV American Airlines airfares from Los Angeles in December
$692 Depart: 12/10/2014
Return: 12/21/2014

provided by FareDepot

American AirlinesDenver To Fort Worth American Airlines airfares from Denver in January
$123 Depart: 01/13/2015
Return: 01/28/2015

provided by FlightHub

Etihad AirwaysOrlando To Mumbai Etihad Airways airfares from Orlando in December
$2464 Depart: 12/18/2014
Return: 01/11/2015

provided by FlightHub

Asiana AirlinesSeattle To Osaka Asiana Airlines airfares from Seattle in December
$1579 Depart: 12/30/2014
Return: 01/10/2015

provided by FlightHub

Major US CarrierLos Angeles To Puerto Plata Major US Carrier airfares from Los Angeles in February
$1472 Depart: 02/04/2015
Return: 02/09/2015

provided by Faregeek

WestjetHamilton, ON To Edmonton Westjet airfares from Hamilton, ON in December
$787 Depart: 12/14/2014
Return: 12/26/2014

provided by FlyFar

Multiple AirlinesAtlanta To Key West Multiple Airlines airfares from Atlanta in December
$506 Depart: 12/12/2014
Return: 12/19/2014

provided by FareDepot

Jetblue AirwaysWashington DC To Buffalo Jetblue Airways airfares from Washington DC in November
$223 Depart: 11/25/2014
Return: 12/02/2014

provided by FlightHub

Multiple AirlinesVancouver To Roanoke Multiple Airlines airfares from Vancouver in December
$794 Depart: 12/17/2014
Return: 12/24/2014

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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