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)
From
DecJanFebMarAprMayJunJulAugSepOctNov
$330$344$411$529$480$460$526$523check
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Chicago 

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Check our newest flight offers to Caribbean:

  • $344US Airways flight US Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)01/01/201502:55 pm
    San Juan, PR (SJU)Chicago, IL (ORD)01/11/201508:44 pm
    faregeek.com check price
  • $454US Airways flight US Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)02/11/201507:25 am
    Nassau, BS (NAS)Chicago, IL (ORD)02/15/201510:20 am
    faregeek.com check price
  • $483American Airlines flight American Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Punta Cana, DO (PUJ)04/15/201507:30 am
    Punta Cana, DO (PUJ)Chicago, IL (ORD)04/23/201502:34 pm
    faredepot.com check price
  • $493Air Canada flight Air Canada 
    FromToDepartureTime
    Chicago, IL (ORD)Bridgetown, BB (BGI)01/20/201508:20 pm
    Bridgetown, BB (BGI)Chicago, IL (ORD)01/28/201505:20 pm
    faredepot.com check price
  • $533Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)04/04/201506:55 pm
    St. Thomas Island, VI (STT)Chicago, IL (ORD)04/11/201505:10 pm
    faredepot.com check price
cheap domestic and international flights

Recently found cheap flight deals

US AirwaysToronto To Fort Walton Beach US Airways airfares from Toronto in March
$800 Depart: 03/28/2015
Return: 04/04/2015

provided by FlightHub

Qatar AirwaysChicago To Kilimanjaro Qatar Airways airfares from Chicago in November
$1450 Depart: 11/14/2014
Return: 11/24/2014

provided by FlightHub

China Eastern AirlinesDallas To Taipei China Eastern Airlines airfares from Dallas in June
$3614 Depart: 06/04/2015
Return: 07/16/2015

provided by Cheapoair.com

United AirlinesOrange County To Guadalajara United Airlines airfares from Orange County in January
$393 Depart: 01/14/2015
Return: 01/20/2015

provided by FlightHub

Korean AirAnchorage To Bangkok Korean Air airfares from Anchorage in March
$3613 Depart: 03/03/2015
Return: 03/12/2015

provided by Cheapoair.com

US AirwaysNewark To Tallahassee US Airways airfares from Newark in December
$601 Depart: 12/26/2014
Return: 01/03/2015

provided by FlightHub

US AirwaysBaltimore To Oranjestad US Airways airfares from Baltimore in May
$515 Depart: 05/22/2015
Return: 05/29/2015

provided by FlightHub

American AirlinesDetroit To Saint Louis American Airlines airfares from Detroit in December
$346 Depart: 12/10/2014
Return: 12/24/2014

provided by Faregeek

Multiple AirlinesEdmonton To London Multiple Airlines airfares from Edmonton in December
$1278 Depart: 12/15/2014
Return: 12/28/2014

provided by Flightnetwork

 

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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