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:

  • $325United Airlines flight United Airlines 
    Chicago, IL (ORD)San Juan, PR (SJU)08/29/201408:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)10/03/201402:50 pm check price
  • $365Major US Carrier flight Major US Carrier 
    Chicago, IL (ORD)Nassau, BS (NAS)08/24/201407:25 am
    Nassau, BS (NAS)Chicago, IL (ORD)08/30/201412:55 pm check price
  • $468US Airways flight US Airways 
    Chicago, IL (ORD)St. Croix Island, VI (STX)10/14/201406:55 pm
    St. Croix Island, VI (STX)Chicago, IL (ORD)10/19/201404:08 pm check price
  • $486Multiple Airlines flight Multiple Airlines 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)09/01/201408:45 am
    Punta Cana, DO (PUJ)Chicago, IL (ORD)09/06/201412:31 pm check price
  • $523Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Santo Domingo, DO (SDQ)09/01/201408:50 am
    Santo Domingo, DO (SDQ)Chicago, IL (ORD)09/06/201408:15 am check price
cheap domestic and international flights

Recently found cheap flight deals

LufthansaChicago To Tehran Lufthansa airfares from Chicago in August
$1388 Depart: 08/05/2014
Return: 08/21/2014

provided by FlightHub

Multiple AirlinesAtlanta To Colorado Springs Multiple Airlines airfares from Atlanta in September
$781 Depart: 09/17/2014
Return: 09/23/2014

provided by Expedia

Delta AirlinesToronto To South Bend Delta Airlines airfares from Toronto in August
$572 Depart: 08/06/2014
Return: 08/13/2014

provided by FlightHub

American AirlinesBuffalo To Los Angeles American Airlines airfares from Buffalo in October
$524 Depart: 10/08/2014
Return: 10/13/2014

provided by FareDepot

Multiple AirlinesGrand Rapids To Fort Lauderdale Multiple Airlines airfares from Grand Rapids in July
$567 Depart: 07/31/2014
Return: 08/03/2014

provided by FareDepot

KLM Royal Dutch AirlinesSeattle To Delhi KLM Royal Dutch Airlines airfares from Seattle in December
$1876 Depart: 12/12/2014
Return: 12/27/2014

provided by FlightHub

Emirates AirlinesDallas To Tokyo Emirates Airlines airfares from Dallas in August
$1799 Depart: 08/23/2014
Return: 08/31/2014

provided by FlightHub

American AirlinesMiami To Jacksonville American Airlines airfares from Miami in August
$284 Depart: 08/06/2014
Return: 08/21/2014

provided by FareDepot

Hawaiian AirlinesPortland To Honolulu Hawaiian Airlines airfares from Portland in September
$607 Depart: 09/12/2014
Return: 09/19/2014

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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