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:

  • $361Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Ponce, PR (PSE)02/20/201806:49 pm
    Ponce, PR (PSE)Chicago, IL (ORD)03/07/201809:57 am check price
  • $364Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)San Juan, PR (SJU)02/20/201807:00 am
    San Juan, PR (SJU)Chicago, IL (ORD)03/07/201806:30 pm check price
  • $395Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)Port Au Prince, HT (PAP)12/09/201706:19 pm
    Port Au Prince, HT (PAP)Chicago, IL (ORD)12/14/201710:07 am check price
  • $398Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Santo Domingo, DO (SDQ)01/31/201807:00 am
    Santo Domingo, DO (SDQ)Chicago, IL (ORD)02/14/201803:29 pm check price
  • $434Copa Air flight Copa Air 
    Chicago, IL (ORD)Santiago, DO (STI)11/12/201701:25 pm
    Santiago, DO (STI)Chicago, IL (ORD)11/22/201703:57 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Southwest AirlinesAnaheim To Las Vegas Southwest Airlines airfares from Anaheim in March
$138 Depart: 03/09/2018
Return: 03/11/2018

provided by Flightnetwork

LufthansaGreensboro To Paris Lufthansa airfares from Greensboro in October
$5086 Depart: 10/25/2017
Return: 11/01/2017

provided by FlightHub

Copa AirChicago To Tegucigalpa Copa Air airfares from Chicago in October
$572 Depart: 10/21/2017
Return: 10/30/2017

provided by FlightHub

Jetblue AirwaysPittsburgh To Seattle Jetblue Airways airfares from Pittsburgh in December
$896 Depart: 12/22/2017
Return: 01/02/2018

provided by

United AirlinesToronto To Bozeman United Airlines airfares from Toronto in November
$497 Depart: 11/13/2017
Return: 11/21/2017

provided by FlyFar

Multiple AirlinesDetroit To Lisbon Multiple Airlines airfares from Detroit in October
$1046 Depart: 10/17/2017
Return: 10/25/2017

provided by

Multiple AirlinesSan Francisco To Springfield Multiple Airlines airfares from San Francisco in November
$742 Depart: 11/01/2017
Return: 11/06/2017

provided by Flightnetwork

United AirlinesAtlanta To Tulsa United Airlines airfares from Atlanta in October
$416 Depart: 10/24/2017
Return: 10/31/2017

provided by FlightHub

AeromexicoAtlanta To Managua Aeromexico airfares from Atlanta in January
$942 Depart: 01/30/2018
Return: 02/07/2018

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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