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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DecJanFebMarAprMayJunJulAugSepOctNov
$513$222$361$394check
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Chicago 

Check our newest flight offers to Caribbean:

  • $297Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Ponce, PR (PSE)01/19/201810:48 am
    Ponce, PR (PSE)Chicago, IL (ORD)01/24/201811:10 am
    flighthub.com check price
  • $341Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Hamilton, BM (BDA)01/23/201810:48 am
    Hamilton, BM (BDA)Chicago, IL (ORD)02/07/201808:30 am
    flighthub.com check price
  • $372Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)San Juan, PR (SJU)01/19/201807:00 am
    San Juan, PR (SJU)Chicago, IL (ORD)01/24/201811:44 am
    flighthub.com check price
  • $410Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Port Au Prince, HT (PAP)01/03/201806:19 pm
    Port Au Prince, HT (PAP)Chicago, IL (ORD)01/17/201810:07 am
    flightnetwork.com check price
  • $411Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)St. Croix Island, VI (STX)01/17/201807:00 am
    St. Croix Island, VI (STX)Chicago, IL (ORD)02/01/201808:55 am
    cheapoair.com check price
cheap domestic and international flights

Recently found cheap flight deals

LufthansaSeattle To Jakarta Lufthansa airfares from Seattle in December
$5230 Depart: 12/30/2017
Return: 01/07/2018

provided by FlightHub

Multiple AirlinesGrand Rapids To Yuma Multiple Airlines airfares from Grand Rapids in May
$527 Depart: 05/16/2017
Return: 05/31/2017

provided by Travelgrove

Virgin AmericaSan Diego To Denver Virgin America airfares from San Diego in January
$346 Depart: 01/03/2018
Return: 01/16/2018

provided by FlightHub

Multiple AirlinesCalgary To Rome Multiple Airlines airfares from Calgary in November
$1505 Depart: 11/23/2017
Return: 11/30/2017

provided by Flightnetwork

Multiple AirlinesDallas To Taipei Multiple Airlines airfares from Dallas in December
$1540 Depart: 12/25/2017
Return: 01/22/2018

provided by FlightHub

Multiple AirlinesDetroit To Guatemala City Multiple Airlines airfares from Detroit in January
$1131 Depart: 01/30/2018
Return: 02/14/2018

provided by FlightHub

United AirlinesSalt Lake City To Sacramento United Airlines airfares from Salt Lake City in December
$410 Depart: 12/24/2017
Return: 01/05/2018

provided by FlyFar

American AirlinesNewport News To Chicago American Airlines airfares from Newport News in February
$228 Depart: 02/27/2017
Return: 03/13/2017

provided by Travelgrove

Multiple AirlinesChicago To Saint Louis Multiple Airlines airfares from Chicago in January
$289 Depart: 01/13/2018
Return: 01/25/2018

provided by FlyFar

 

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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