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)
From
SepOctNovDecJanFebMarAprMayJunJulAug
$407$274$238$310$410$330$367$394check
fares
$335$388check
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more
Chicago 

Check our newest flight offers to Caribbean:

  • $238Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)11/06/201607:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)11/11/201607:55 pm
    flighthub.com check price
  • $341Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Ponce, PR (PSE)02/12/201705:59 pm
    Ponce, PR (PSE)Chicago, IL (ORD)02/19/201706:00 am
    flighthub.com check price
  • $343Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)10/15/201605:15 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)10/20/201604:17 pm
    flyfar.ca check price
  • $349Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)02/12/201705:59 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)02/19/201701:58 am
    flighthub.com check price
  • $373Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)02/08/201705:59 pm
    Hamilton, BM (BDA)Chicago, IL (ORD)02/14/201703:45 pm
    flighthub.com check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesPeoria To Minneapolis Multiple Airlines airfares from Peoria in October
$732 Depart: 10/03/2016
Return: 10/09/2016

provided by FlyFar

Thy Turkish AirlinesAtlanta To Karachi Thy Turkish Airlines airfares from Atlanta in August
$1622 Depart: 08/01/2016
Return: 08/08/2016

provided by Cheapoair.com

Southwest AirlinesNew York City To Tampa Southwest Airlines airfares from New York City in October
$285 Depart: 10/10/2016
Return: 10/20/2016

provided by Flightnetwork

Multiple AirlinesHouston To Kiev Multiple Airlines airfares from Houston in November
$960 Depart: 11/05/2016
Return: 11/26/2016

provided by FlightHub

Multiple AirlinesToronto To Larnaca Multiple Airlines airfares from Toronto in December
$2054 Depart: 12/21/2016
Return: 01/04/2017

provided by FlightHub

Multiple AirlinesPhiladelphia To Manchester Multiple Airlines airfares from Philadelphia in January
$1085 Depart: 01/10/2017
Return: 01/18/2017

provided by FlyFar

Finn AirLas Vegas To Milan Finn Air airfares from Las Vegas in October
$1446 Depart: 10/01/2016
Return: 10/15/2016

provided by Cheapoair.com

Multiple AirlinesNew York City To Zadar Multiple Airlines airfares from New York City in November
$1128 Depart: 11/05/2016
Return: 11/10/2016

provided by FlyFar

Multiple AirlinesWindsor To Kona Multiple Airlines airfares from Windsor in September
$1074 Depart: 09/08/2016
Return: 09/15/2016

provided by FareDepot

 

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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