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:

  • $373Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Nassau, BS (NAS)07/12/201707:00 am
    Nassau, BS (NAS)Chicago, IL (ORD)08/02/201711:00 am check price
  • $407United Airlines flight United Airlines 
    Chicago, IL (ORD)San Juan, PR (SJU)05/12/201707:30 am
    San Juan, PR (SJU)Chicago, IL (ORD)05/24/201702:10 pm check price
  • $421Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Freeport, BS (FPO)07/12/201707:00 am
    Freeport, BS (FPO)Chicago, IL (ORD)08/02/201705:25 pm check price
  • $424Multiple Airlines flight Multiple Airlines 
    Chicago, IL (ORD)Aguadilla, PR (BQN)04/19/201706:30 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)04/29/201701:45 am check price
  • $467United Airlines flight United Airlines 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)04/01/201701:15 pm
    Punta Cana, DO (PUJ)Chicago, IL (ORD)04/08/201702:05 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Korean AirWashington DC To Changi Korean Air airfares from Washington DC in September
$1364 Depart: 09/01/2017
Return: 09/10/2017

provided by FlightHub

Multiple AirlinesNew York City To Monterrey Multiple Airlines airfares from New York City in April
$3512 Depart: 04/18/2017
Return: 05/03/2017

provided by Travelgrove

Alaska AirlinesOrange County To Oakland Alaska Airlines airfares from Orange County in April
$425 Depart: 04/27/2017
Return: 05/05/2017

provided by FlyFar

LufthansaPhoenix To Tel Aviv Lufthansa airfares from Phoenix in June
$1462 Depart: 06/17/2017
Return: 07/09/2017

provided by Flightnetwork

Alaska AirlinesTulsa To Portland Alaska Airlines airfares from Tulsa in April
$485 Depart: 04/12/2017
Return: 04/19/2017

provided by FlyFar

Jetblue AirwaysOakland To Chicago Jetblue Airways airfares from Oakland in July
$657 Depart: 07/31/2017
Return: 08/07/2017

provided by FlyFar

Multiple AirlinesDallas To Toulouse Multiple Airlines airfares from Dallas in February
$1746 Depart: 02/15/2017
Return: 02/22/2017

provided by FlightHub

Jetblue AirwaysSan Francisco To Burbank Jetblue Airways airfares from San Francisco in March
$702 Depart: 03/29/2017
Return: 04/05/2017

provided by

Multiple AirlinesFort Lauderdale To Portland Multiple Airlines airfares from Fort Lauderdale in May
$498 Depart: 05/09/2017
Return: 05/15/2017

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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