Cheap flights from Chicago to Caribbean
Travel > Caribbean
Travel tip: Visit Ponce on your holidays!Check our current prices for flights from Chicago to Caribbean. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Chicago to Caribbean, you will need to run a search below.
Search and Compare cheap Flights

Book your flight now with Cheapoair.com and save!
Cheap San Juan airfares from $169/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/11/2025, 08:46 pm from Chicago O`hare (ORD) airport and arrives at San Juan Marin Intl (SJU) at 02:27 am. The flight time is 5 hours and 41 minutes. The Returning flight departes on 03/19/2025, 03:05 am (other return dates are also available). Date posted: 06 Feb 2025
Price evolution for flights From Chicago To Caribbean

Recent Deals on Flights from Chicago to Caribbean:Roundtrip / Oneway
- $169
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 03/11/2025 08:46 pm San Juan, PR (SJU) Chicago, IL (ORD) 03/19/2025 03:05 am - $179
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 02/28/2025 07:18 pm San Juan, PR (SJU) Chicago, IL (ORD) 03/12/2025 06:00 am - $179
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 02/28/2025 04:44 pm San Juan, PR (SJU) Chicago, IL (ORD) 03/12/2025 06:00 am - $256
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) San Juan, PR (SJU) 03/08/2025 07:00 am San Juan, PR (SJU) Chicago, IL (ORD) 03/16/2025 03:35 pm - $265
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) St. Thomas Island, VI (STT) 02/22/2025 03:14 pm St. Thomas Island, VI (STT) Chicago, IL (ORD) 03/07/2025 12:11 pm - $103
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Aguadilla, PR (BQN) 02/26/2025 07:18 pm - $107
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) St. Thomas Island, VI (STT) 02/19/2025 07:10 am - $113
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) St. Thomas Island, VI (STT) 02/21/2025 03:14 pm - $130
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Saint Maarten, AN (SXM) 03/03/2025 05:00 am - $148
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Punta Cana, DO (PUJ) 03/10/2025 07:42 pm
Recently found cheap flight deals
Dayton To Honolulu Alaska Airlines airfares from Dayton in December
$2345 Depart: 12/16/2023
Return: 12/30/2023
provided by Cheapoair.com
Roanoke To Orlando Oceanic Airlines airfares from Roanoke in August
$13273 Depart: 08/09/2020
Return: 08/23/2020
provided by FlyFar
Buffalo To Bucharest Multiple Airlines airfares from Buffalo in August
$1299 Depart: 08/17/2024
Return: 08/22/2024
provided by Cheapoair.com
Portland To Puerto Vallarta Multiple Airlines airfares from Portland in April
$467 Depart: 04/29/2025
Return: 05/07/2025
provided by Cheapoair.com
Los Angeles To Lihue Alaska Airlines airfares from Los Angeles in September
$2279 Depart: 09/13/2024
Return: 09/27/2024
provided by Cheapoair.com
Omaha To Miami Frontier Airlines airfares from Omaha in December
$178 Depart: 12/06/2024
Return: 12/18/2024
provided by Cheapoair.com
Rochester To Las Vegas Multiple Airlines airfares from Rochester in March
$989 Depart: 03/20/2024
Return: 03/29/2024
provided by Cheapoair.com
Philadelphia To Fort Myers Multiple Airlines airfares from Philadelphia in February
$155 Depart: 02/25/2025
Return: 03/04/2025
provided by Cheapoair.com
Toledo To Athens Iberia Airlines airfares from Toledo in March
$2294 Depart: 03/28/2020
Return: 04/09/2020
provided by Flightnetwork
Specify your search details. Browse the cheapest flights from Chicago to Caribbean, Caribbean hotel rooms and Chicago to Caribbean vacation packages from the most popular providers, airline consolidators and travel search engines.