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
OctNovDecJanFebMarAprMayJunJulAugSep
$494$357$330$322$464$529$531$460$526$345check
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Chicago 

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Check our newest flight offers to Caribbean:

  • $322Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)01/14/201508:25 am
    San Juan, PR (SJU)Chicago, IL (ORD)01/20/201504:10 pm
    faredepot.com check price
  • $330US Airways flight US Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)12/01/201404:00 pm
    Montego Bay, JM (MBJ)Chicago, IL (ORD)12/05/201401:45 pm
    flighthub.com check price
  • $387United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Grand Cayman, KY (GCM)12/06/201406:07 pm
    Grand Cayman, KY (GCM)Chicago, IL (ORD)12/14/201405:41 pm
    faredepot.com check price
  • $428United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)01/14/201501:55 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)01/20/201502:55 am
    flighthub.com check price
  • $503United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Punta Cana, DO (PUJ)01/02/201509:00 pm
    Punta Cana, DO (PUJ)Chicago, IL (ORD)01/09/201504:55 pm
    flighthub.com check price
cheap domestic and international flights

Recently found cheap flight deals

United AirlinesAtlanta To Zurich United Airlines airfares from Atlanta in November
$1242 Depart: 11/26/2014
Return: 12/10/2014

provided by FlightHub

Multiple AirlinesAtlanta To Moscow Multiple Airlines airfares from Atlanta in September
$1134 Depart: 09/10/2014
Return: 09/24/2014

provided by Cheapoair.com

United AirlinesNew York City To New Orleans United Airlines airfares from New York City in July
$355 Depart: 07/30/2015
Return: 08/03/2015

provided by FlightHub

US AirwaysSan Francisco To Gainesville US Airways airfares from San Francisco in December
$526 Depart: 12/13/2014
Return: 12/22/2014

provided by FlightHub

Multiple AirlinesNew York City To Turin Multiple Airlines airfares from New York City in November
$1069 Depart: 11/26/2014
Return: 12/02/2014

provided by FlightHub

US AirwaysTucson To Seattle US Airways airfares from Tucson in December
$363 Depart: 12/11/2014
Return: 12/18/2014

provided by FlightHub

Multiple AirlinesPhoenix To Phnom Penh Multiple Airlines airfares from Phoenix in December
$1744 Depart: 12/24/2014
Return: 12/31/2014

provided by FlightHub

Multiple AirlinesColumbus To Las Vegas Multiple Airlines airfares from Columbus in December
$449 Depart: 12/17/2014
Return: 12/31/2014

provided by FlightHub

Multiple AirlinesPhoenix To Lvov Multiple Airlines airfares from Phoenix in November
$1112 Depart: 11/25/2014
Return: 12/10/2014

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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