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)
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MayJunJulAugSepOctNovDecJanFebMarApr
$316$422$348$610$424$2562check
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Chicago 

Check our newest flight offers to Caribbean:

  • $283Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Salvador, SV (SAL)05/25/202205:00 am
    San Salvador, SV (SAL)Chicago, IL (ORD)05/31/202212:13 pm
    cheapoair.com check price
  • $316Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)05/31/202205:30 pm
    San Juan, PR (SJU)Chicago, IL (ORD)06/09/202206:30 am
    cheapoair.com check price
  • $370Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Santiago, DO (STI)05/29/202208:00 am
    Santiago, DO (STI)Chicago, IL (ORD)06/03/202202:47 am
    cheapoair.com check price
  • $422Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)06/14/202210:18 am
    Port Au Prince, HT (PAP)Chicago, IL (ORD)06/22/202210:01 am
    cheapoair.com check price
  • $463Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Montego Bay, JM (MBJ)05/22/202205:05 am
    Montego Bay, JM (MBJ)Chicago, IL (ORD)05/29/202201:15 pm
    cheapoair.com check price
cheap domestic and international flights

Recently found cheap flight deals

Itali AirlinesMemphis To Tampa Itali Airlines airfares from Memphis in September
$455 Depart: 09/25/2020
Return: 10/04/2020

provided by Cheapoair.com

Alaska AirlinesPhoenix To Pasco Alaska Airlines airfares from Phoenix in June
$573 Depart: 06/24/2022
Return: 07/04/2022

provided by Cheapoair.com

Multiple AirlinesNew York City To Santa Cruz Multiple Airlines airfares from New York City in August
$788 Depart: 08/18/2021
Return: 08/31/2021

provided by Cheapoair.com

Multiple AirlinesToronto To Malaga Multiple Airlines airfares from Toronto in July
$953 Depart: 07/05/2022
Return: 07/13/2022

provided by Cheapoair.com

Alaska AirlinesHouston To Great Falls Alaska Airlines airfares from Houston in June
$1130 Depart: 06/11/2022
Return: 06/16/2022

provided by Cheapoair.com

Multiple AirlinesNew York City To Santiago De Compostela Multiple Airlines airfares from New York City in June
$982 Depart: 06/20/2022
Return: 06/25/2022

provided by Cheapoair.com

Multiple AirlinesSalt Lake City To Philadelphia Multiple Airlines airfares from Salt Lake City in May
$660 Depart: 05/20/2022
Return: 05/31/2022

provided by Cheapoair.com

Frontier AirlinesColumbus To Denver Frontier Airlines airfares from Columbus in May
$441 Depart: 05/29/2022
Return: 06/05/2022

provided by Cheapoair.com

Multiple AirlinesToronto To Cartagena Multiple Airlines airfares from Toronto in June
$545 Depart: 06/29/2022
Return: 07/05/2022

provided by Cheapoair.com

 

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
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