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!

Check current prices for flights to Caribbean at our partners' sites:

Search and Compare cheap Flights

Enter your travel details:Step 1

Select merchants to compare:Step 2

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:

  • $275Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)San Juan, PR (SJU)10/19/201511:20 am
    San Juan, PR (SJU)Chicago, IL (ORD)10/23/201501:40 pm check price
  • $393Spirit Airlines flight Spirit Airlines 
    Chicago, IL (ORD)San Salvador, SV (SAL)12/02/201506:40 pm
    San Salvador, SV (SAL)Chicago, IL (ORD)12/05/201502:20 am check price
  • $424American Airlines flight American Airlines 
    Chicago, IL (ORD)Montego Bay, JM (MBJ)12/08/201505:35 am
    Montego Bay, JM (MBJ)Chicago, IL (ORD)12/16/201501:27 pm check price
  • $427American Airlines flight American Airlines 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)10/28/201506:00 am
    Punta Cana, DO (PUJ)Chicago, IL (ORD)11/10/201504:59 pm check price
  • $441American Airlines flight American Airlines 
    Chicago, IL (ORD)Trinidad, TT (POS)11/10/201504:45 pm
    Trinidad, TT (POS)Chicago, IL (ORD)11/24/201503:45 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesAlbuquerque To New York City Multiple Airlines airfares from Albuquerque in December
$415 Depart: 12/29/2015
Return: 01/13/2016

provided by FlyFar

Multiple AirlinesWashington DC To Killeen Multiple Airlines airfares from Washington DC in November
$474 Depart: 11/25/2015
Return: 12/09/2015

provided by FlyFar

Multiple AirlinesDayton To Washington DC Multiple Airlines airfares from Dayton in December
$229 Depart: 12/29/2015
Return: 01/13/2016

provided by FlightHub

LOT Polish AirlinesChicago To Minsk LOT Polish Airlines airfares from Chicago in July
$1465 Depart: 07/22/2015
Return: 08/04/2015

provided by FlyFar

Multiple AirlinesMiami To Maracaibo Multiple Airlines airfares from Miami in September
$1650 Depart: 09/16/2015
Return: 10/07/2015

provided by Tripsta

Jetblue AirwaysNewark To Cancun Jetblue Airways airfares from Newark in March
$532 Depart: 03/05/2016
Return: 03/11/2016

provided by FlightHub

Multiple AirlinesFresno To Guadalajara Multiple Airlines airfares from Fresno in October
$369 Depart: 10/14/2015
Return: 10/19/2015

provided by FlightHub

United AirlinesMilwaukee To Jackson United Airlines airfares from Milwaukee in November
$336 Depart: 11/12/2015
Return: 11/18/2015

provided by FareDepot

United AirlinesPortland To Maui United Airlines airfares from Portland in December
$607 Depart: 12/11/2015
Return: 12/18/2015

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

   Welcome to Travelgrove  register tell a friend bookmark it 
This airfare deal was found   ago. Click "Check price" to see current prices!