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:

  • $352US Airways flight US Airways 
    Chicago, IL (ORD)San Juan, PR (SJU)08/13/201508:30 am
    San Juan, PR (SJU)Chicago, IL (ORD)08/18/201508:20 pm check price
  • $408Jetblue Airways flight Jetblue Airways 
    Chicago, IL (ORD)Santo Domingo, DO (SDQ)01/19/201610:55 am
    Santo Domingo, DO (SDQ)Chicago, IL (ORD)01/26/201606:09 am check price
  • $427American Airlines flight American Airlines 
    Chicago, IL (ORD)Nassau, BS (NAS)11/10/201511:41 am
    Nassau, BS (NAS)Chicago, IL (ORD)11/15/201506:50 pm check price
  • $474US Airways flight US Airways 
    Chicago, IL (ORD)Grand Cayman, KY (GCM)09/15/201507:04 am
    Grand Cayman, KY (GCM)Chicago, IL (ORD)09/28/201501:00 pm check price
  • $477United Airlines flight United Airlines 
    Chicago, IL (ORD)Punta Cana, DO (PUJ)01/19/201609:00 am
    Punta Cana, DO (PUJ)Chicago, IL (ORD)01/26/201602:20 pm check price
cheap domestic and international flights

Recently found cheap flight deals

US AirwaysMemphis To New York City US Airways airfares from Memphis in September
$313 Depart: 09/18/2015
Return: 09/20/2015

provided by FlyFar

Multiple AirlinesLos Angeles To Salt Lake City Multiple Airlines airfares from Los Angeles in August
$266 Depart: 08/05/2015
Return: 08/10/2015

provided by FareDepot

Air LingusSan Francisco To Rome Air Lingus airfares from San Francisco in March
$1336 Depart: 03/31/2016
Return: 04/10/2016

provided by

Multiple AirlinesChicago To Vadodara Multiple Airlines airfares from Chicago in November
$1536 Depart: 11/13/2015
Return: 01/26/2016

provided by FlightHub

Multiple AirlinesLong Beach To Bombay Multiple Airlines airfares from Long Beach in September
$7068 Depart: 09/02/2015
Return: 09/15/2015

provided by Tripsta

US AirwaysNew Orleans To Buffalo US Airways airfares from New Orleans in August
$405 Depart: 08/05/2015
Return: 08/12/2015

provided by Tripsta

Multiple AirlinesSeattle To Louisville Multiple Airlines airfares from Seattle in December
$1103 Depart: 12/20/2015
Return: 12/27/2015

provided by Travelgrove

Air CanadaVancouver To Cabo San Lucas Air Canada airfares from Vancouver in August
$559 Depart: 08/29/2015
Return: 09/05/2015

provided by

Multiple AirlinesNew York City To Reno Multiple Airlines airfares from New York City in September
$354 Depart: 09/19/2015
Return: 09/26/2015

provided by FareDepot


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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