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)
From
JulAugSepOctNovDecJanFebMarAprMayJun
$311$108$269$466check
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Chicago 

Check our newest flight offers to Caribbean:

  • $108Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Thomas Island, VI (STT)08/12/202005:20 am
    St. Thomas Island, VI (STT)Chicago, IL (ORD)08/19/202002:30 pm
    flyfar.ca check price
  • $192Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)08/22/202006:28 pm
    San Juan, PR (SJU)Chicago, IL (ORD)08/30/202002:11 pm
    cheapoair.com check price
  • $264Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)08/14/202005:09 am
    Port Au Prince, HT (PAP)Chicago, IL (ORD)08/25/202009:57 am
    flyfar.ca check price
  • $269Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Nassau, BS (NAS)09/03/202005:09 am
    Nassau, BS (NAS)Chicago, IL (ORD)09/18/202006:51 pm
    cheapoair.com check price
  • $321Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Aguadilla, PR (BQN)08/04/202007:08 pm
    Aguadilla, PR (BQN)Chicago, IL (ORD)08/11/202002:29 am
    flyfar.ca check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesSan Francisco To Riga Multiple Airlines airfares from San Francisco in March
$1246 Depart: 03/14/2017
Return: 03/22/2017

provided by FlightHub

Multiple AirlinesNewark To Bangalore Multiple Airlines airfares from Newark in July
$744 Depart: 07/29/2020
Return: 08/04/2020

provided by FlyFar

United AirlinesNewark To Ontario, London United Airlines airfares from Newark in October
$845 Depart: 10/17/2019
Return: 10/30/2019

provided by Cheapoair.com

Frontier AirlinesTrenton To Atlanta Frontier Airlines airfares from Trenton in August
$184 Depart: 08/05/2020
Return: 08/19/2020

provided by FlyFar

AeromexicoHouston To San Jose Aeromexico airfares from Houston in August
$475 Depart: 08/12/2020
Return: 08/27/2020

provided by Cheapoair.com

Multiple AirlinesManchester, NH To Miami Multiple Airlines airfares from Manchester, NH in July
$862 Depart: 07/26/2019
Return: 08/01/2019

provided by FlyFar

Oceanic AirlinesMemphis To Charlotte Oceanic Airlines airfares from Memphis in July
$7907 Depart: 07/26/2020
Return: 08/05/2020

provided by FlyFar

WestjetLos Angeles To Kitchener Westjet airfares from Los Angeles in February
$684 Depart: 02/16/2020
Return: 02/26/2020

provided by Cheapoair.com

Alaska AirlinesWashington DC To Spokane Alaska Airlines airfares from Washington DC in August
$461 Depart: 08/25/2019
Return: 09/03/2019

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
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