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
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Check our newest flight offers to Caribbean:
- $685
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Montego Bay, JM (MBJ) 05/13/2025 05:05 am Montego Bay, JM (MBJ) Chicago, IL (ORD) 05/28/2025 03:33 pm - $2351 Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Hamilton, BM (BDA) 06/10/2025 10:20 pm Hamilton, BM (BDA) Chicago, IL (ORD) 06/24/2025 07:50 pm - $2710 Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Hamilton, BM (BDA) 07/02/2025 10:25 pm Hamilton, BM (BDA) Chicago, IL (ORD) 07/15/2025 07:50 pm - $3970
British Airways
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) St. Lucia, LC (UVF) 05/21/2025 04:55 pm St. Lucia, LC (UVF) Chicago, IL (ORD) 05/28/2025 08:25 pm - $4840 Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Nassau, BS (NAS) 04/30/2025 01:16 pm Nassau, BS (NAS) Chicago, IL (ORD) 05/06/2025 10:05 pm
Recently found cheap flight deals
Ottawa To Newark Air Transat airfares from Ottawa in March
$267 Depart: 03/26/2025
Return: 04/03/2025
provided by Cheapoair.com
Las Vegas To Memphis Spirit Airlines airfares from Las Vegas in March
$129 Depart: 03/17/2025
Return: 03/25/2025
provided by Cheapoair.com
Los Angeles To Chisinau Multiple Airlines airfares from Los Angeles in February
$948 Depart: 02/27/2024
Return: 03/05/2024
provided by Cheapoair.com
Dallas To Palermo Multiple Airlines airfares from Dallas in December
$3161 Depart: 12/29/2023
Return: 01/13/2024
provided by Cheapoair.com
Oklahoma City To Baltimore Frontier Airlines airfares from Oklahoma City in March
$718 Depart: 03/11/2025
Return: 03/26/2025
provided by Cheapoair.com
Baltimore To Santa Cruz Multiple Airlines airfares from Baltimore in March
$2542 Depart: 03/27/2025
Return: 04/07/2025
provided by Cheapoair.com
Denver To Hanoi Asiana Airlines airfares from Denver in April
$1397 Depart: 04/20/2025
Return: 04/29/2025
provided by Cheapoair.com
Miami To Port Au Prince Multiple Airlines airfares from Miami in December
$1550 Depart: 12/01/2024
Return: 12/09/2024
provided by Cheapoair.com
Chicago To Sacramento Spirit Airlines airfares from Chicago in April
$141 Depart: 04/09/2025
Return: 04/22/2025
provided by Cheapoair.com
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