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)
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OctNovDecJanFebMarAprMayJunJulAugSep
$288$240$222$337$297$485check
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Chicago 

Check our newest flight offers to Caribbean:

  • $222Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)12/02/201806:23 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)12/10/201804:28 am
    flyfar.ca check price
  • $266Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)11/08/201803:15 pm
    Port Au Prince, HT (PAP)Chicago, IL (ORD)11/14/201810:07 am
    flightnetwork.com check price
  • $295Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Croix Island, VI (STX)10/22/201804:24 pm
    St. Croix Island, VI (STX)Chicago, IL (ORD)11/04/201804:05 pm
    cheapoair.com check price
  • $297Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)02/26/201907:00 am
    San Juan, PR (SJU)Chicago, IL (ORD)03/06/201906:43 pm
    cheapoair.com check price
  • $382Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)02/05/201905:15 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)02/20/201912:55 pm
    cheapoair.com check price
cheap domestic and international flights

Recently found cheap flight deals

Emirates AirlinesDallas To Cochin Emirates Airlines airfares from Dallas in October
$1079 Depart: 10/31/2018
Return: 11/13/2018

provided by FlyFar

Emirates AirlinesOrlando To Johannesburg Emirates Airlines airfares from Orlando in June
$1386 Depart: 06/05/2018
Return: 06/19/2018

provided by FlyFar

Multiple AirlinesPhoenix To Wichita Multiple Airlines airfares from Phoenix in October
$358 Depart: 10/23/2018
Return: 10/28/2018

provided by Cheapoair.com

Multiple AirlinesChattanooga To San Juan Multiple Airlines airfares from Chattanooga in October
$3290 Depart: 10/27/2018
Return: 11/02/2018

provided by Cheapoair.com

All Nippon AirwaysSan Francisco To Bombay All Nippon Airways airfares from San Francisco in December
$1821 Depart: 12/22/2018
Return: 01/16/2019

provided by Cheapoair.com

Multiple AirlinesLos Angeles To Luxor Multiple Airlines airfares from Los Angeles in November
$1485 Depart: 11/20/2018
Return: 12/05/2018

provided by Flightnetwork

Multiple AirlinesNew Orleans To San Juan Multiple Airlines airfares from New Orleans in November
$345 Depart: 11/27/2018
Return: 12/05/2018

provided by Flightnetwork

Alaska AirlinesMidland/Odessa To Lihue Alaska Airlines airfares from Midland/Odessa in November
$2671 Depart: 11/17/2018
Return: 12/02/2018

provided by Cheapoair.com

Multiple AirlinesWest Palm Beach To Punta Cana Multiple Airlines airfares from West Palm Beach in November
$1019 Depart: 11/01/2018
Return: 11/12/2018

provided by Cheapoair.com

 

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
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