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:

  • $238Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)San Juan, PR (SJU)11/02/201607:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)11/16/201607:55 pm check price
  • $313Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)Aguadilla, PR (BQN)11/24/201606:25 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)12/09/201604:07 am check price
  • $334Multiple Airlines flight Multiple Airlines 
    Chicago, IL (ORD)St. Thomas Island, VI (STT)12/03/201607:15 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)12/18/201605:04 pm check price
  • $341Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Ponce, PR (PSE)10/24/201608:11 pm
    Ponce, PR (PSE)Chicago, IL (ORD)10/31/201606:55 pm check price
  • $371American Airlines flight American Airlines 
    Chicago, IL (ORD)Belize City, BZ (BZE)12/04/201605:30 am
    Belize City, BZ (BZE)Chicago, IL (ORD)12/14/201603:15 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Jetblue AirwaysBuffalo To San Juan Jetblue Airways airfares from Buffalo in November
$448 Depart: 11/14/2016
Return: 11/19/2016

provided by FlightHub

Southwest AirlinesTampa To Dallas Southwest Airlines airfares from Tampa in December
$566 Depart: 12/20/2016
Return: 12/27/2016

provided by Flightnetwork

Multiple AirlinesBaltimore To Milan Multiple Airlines airfares from Baltimore in November
$989 Depart: 11/21/2016
Return: 12/03/2016

provided by FlyFar

United AirlinesPhoenix To Ithaca United Airlines airfares from Phoenix in February
$387 Depart: 02/01/2017
Return: 02/14/2017

provided by FareDepot

Virgin AmericaSan Francisco To Honolulu Virgin America airfares from San Francisco in October
$588 Depart: 10/26/2016
Return: 11/02/2016

provided by FareDepot

Multiple AirlinesCincinnati To Denver Multiple Airlines airfares from Cincinnati in November
$709 Depart: 11/13/2016
Return: 11/25/2016

provided by Flightnetwork

Thy Turkish AirlinesAtlanta To Munich Thy Turkish Airlines airfares from Atlanta in February
$752 Depart: 02/07/2017
Return: 02/28/2017

provided by FlightHub

Copa AirHouston To Montevideo Copa Air airfares from Houston in December
$1887 Depart: 12/13/2016
Return: 12/27/2016

provided by FlyFar

Multiple AirlinesNewark To Hamilton Multiple Airlines airfares from Newark in October
$7246 Depart: 10/30/2016
Return: 11/09/2016

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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