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:

  • $392United Airlines flight United Airlines 
    Chicago, IL (ORD)San Juan, PR (SJU)07/25/201711:40 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/08/201701:15 am check price
  • $472Copa Air flight Copa Air 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)06/27/201702:25 pm
    Punta Cana, DO (PUJ)Chicago, IL (ORD)07/04/201712:19 pm check price
  • $475Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Nassau, BS (NAS)06/27/201707:00 am
    Nassau, BS (NAS)Chicago, IL (ORD)07/04/201705:25 pm check price
  • $559Aeromexico flight Aeromexico 
    Chicago, IL (ORD)Manzanillo, MX (ZLO)06/27/201703:10 pm
    Manzanillo, MX (ZLO)Chicago, IL (ORD)07/04/201710:20 am check price
  • $575Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Saint Maarten, AN (SXM)08/18/201707:00 am
    Saint Maarten, AN (SXM)Chicago, IL (ORD)08/28/201701:40 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesLos Angeles To Johannesburg Multiple Airlines airfares from Los Angeles in July
$1253 Depart: 07/05/2017
Return: 07/19/2017

provided by

Multiple AirlinesNew Orleans To Beirut Multiple Airlines airfares from New Orleans in August
$1304 Depart: 08/16/2017
Return: 09/06/2017

provided by FlightHub

Multiple AirlinesWichita To San Diego Multiple Airlines airfares from Wichita in July
$548 Depart: 07/04/2017
Return: 07/12/2017

provided by Flightnetwork

United AirlinesSaint Louis To Chicago United Airlines airfares from Saint Louis in August
$285 Depart: 08/03/2017
Return: 08/12/2017

provided by FlightHub

Southwest AirlinesTucson To Columbus Southwest Airlines airfares from Tucson in June
$540 Depart: 06/29/2017
Return: 07/02/2017

provided by Flightnetwork

Multiple AirlinesOklahoma City To Los Angeles Multiple Airlines airfares from Oklahoma City in July
$1640 Depart: 07/16/2017
Return: 07/29/2017

provided by FlightHub

Canadian NorthEdmonton To Ottawa Canadian North airfares from Edmonton in August
$5064 Depart: 08/04/2017
Return: 09/01/2017

provided by FlightHub

AeromexicoDallas To Victoria Aeromexico airfares from Dallas in June
$1046 Depart: 06/27/2017
Return: 07/04/2017

provided by

Multiple AirlinesVancouver To Durham Multiple Airlines airfares from Vancouver in July
$669 Depart: 07/31/2017
Return: 08/08/2017

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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