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!

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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Check our newest flight offers to Caribbean:

  • $299American Airlines flight American Airlines 
    Chicago, IL (ORD)San Juan, PR (SJU)08/07/201408:15 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/12/201403:05 pm check price
  • $420Delta Airlines flight Delta Airlines 
    Chicago, IL (ORD)Hamilton, BM (BDA)06/06/201406:00 am
    Hamilton, BM (BDA)Chicago, IL (ORD)06/13/201409:00 am check price
  • $455United Airlines flight United Airlines 
    Chicago, IL (ORD)Aguadilla, PR (BQN)05/15/201402:15 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)05/30/201402:00 am check price
  • $458American Airlines flight American Airlines 
    Chicago, IL (ORD)St. Croix Island, VI (STX)05/29/201405:30 am
    St. Croix Island, VI (STX)Chicago, IL (ORD)06/02/201402:20 pm check price
  • $463Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)St. Thomas Island, VI (STT)05/29/201409:00 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)06/02/201405:00 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesFort Lauderdale To San Jose, CA Multiple Airlines airfares from Fort Lauderdale in June
$455 Depart: 06/25/2014
Return: 06/30/2014

provided by FlightHub

US AirwaysHouston To Springfield US Airways airfares from Houston in May
$357 Depart: 05/28/2014
Return: 06/10/2014

provided by FlightHub

Multiple AirlinesGrand Rapids To Toronto Multiple Airlines airfares from Grand Rapids in April
$1029 Depart: 04/25/2014
Return: 04/30/2014

provided by Travelgrove

Delta AirlinesSan Francisco To Jackson Delta Airlines airfares from San Francisco in August
$1041 Depart: 08/26/2014
Return: 09/17/2014

provided by FlightHub

Avianca AirlinesWashington DC To Managua Avianca Airlines airfares from Washington DC in August
$823 Depart: 08/05/2014
Return: 08/26/2014

provided by FlightHub

US AirwaysWest Palm Beach To Philadelphia US Airways airfares from West Palm Beach in April
$298 Depart: 04/23/2014
Return: 05/01/2014

provided by FlightHub

United AirlinesHouston To Ithaca United Airlines airfares from Houston in May
$521 Depart: 05/20/2014
Return: 05/25/2014

provided by FareDepot

Air FranceLos Angeles To Mahe Island Air France airfares from Los Angeles in June
$3705 Depart: 06/28/2014
Return: 07/13/2014

provided by Faregeek

Multiple AirlinesAlbuquerque To Portland Multiple Airlines airfares from Albuquerque in October
$284 Depart: 10/01/2013
Return: 10/13/2013

provided by


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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