$161 Find Cheap Flights from Gulfport to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Gulfport to Caribbean Islands departing on 8/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Gulfport to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Gulfport to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Gulfport to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$576
Montego Bay
Montego Bay2 stops$427
Saint Thomas Island
Saint Thomas Island1 stop$530
Bridgetown
Bridgetown2 stops$672
Punta Cana
Punta Cana1 stop$576
Montego Bay
Montego Bay2 stops$427
Saint Thomas Island
Saint Thomas Island1 stop$530
Bridgetown
Bridgetown2 stops$672

Book Cheap Gulfport to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Gulfport to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Gulfport to Caribbean Islands

Tue, Aug 11 - Tue, Aug 25
American Airlines Logo
6:33 pm - 11:37 am
GPT
-
MBJ
17h 04m
2 stops
American Airlines Logo
12:38 pm - 10:44 am
MBJ
-
GPT
22h 06m
2 stops
$427American Airlines
Tue, Aug 11 - Tue, Aug 25
American Airlines Logo
5:35 am - 4:13 pm
GPT
-
MBJ
10h 38m
1 stop
American Airlines Logo
12:47 pm - 10:44 am
MBJ
-
GPT
21h 57m
1 stop
$429American Airlines
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
6:35 pm - 12:48 pm
GPT
-
SJU
17h 13m
2 stops
American Airlines Logo
7:05 am - 10:43 pm
SJU
-
GPT
16h 38m
1 stop
$446American Airlines
Sun, Jun 7 - Thu, Jun 11
Multiple Airlines Logo
7:50 pm - 4:15 am
GPT
-
SJU
31h 25m
2 stops
Multiple Airlines Logo
5:15 pm - 7:41 am
SJU
-
GPT
15h 26m
1 stop
$481Multiple Airlines
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
6:35 pm - 12:48 pm
GPT
-
SJU
17h 13m
2 stops
American Airlines Logo
1:38 pm - 10:43 pm
SJU
-
GPT
10h 05m
2 stops
$486American Airlines
Fri, Jun 5 - Thu, Jun 11
Multiple Airlines Logo
5:31 pm - 11:59 pm
GPT
-
SJU
29h 28m
1 stop
Multiple Airlines Logo
2:36 pm - 7:41 am
SJU
-
GPT
18h 05m
2 stops
$487Multiple Airlines
Wed, Aug 5 - Mon, Aug 10
American Airlines Logo
1:50 pm - 11:59 pm
GPT
-
SJU
9h 09m
1 stop
American Airlines Logo
7:05 am - 10:43 pm
SJU
-
GPT
16h 38m
1 stop
$491American Airlines
Sun, Oct 25 - Wed, Nov 11
Delta Logo
6:00 am - 1:39 pm
GPT
-
STT
6h 39m
1 stop
Delta Logo
3:50 pm - 10:07 pm
STT
-
GPT
8h 17m
1 stop
$530Delta
Sun, Oct 25 - Tue, Nov 10
Delta Logo
6:00 am - 1:39 pm
GPT
-
STT
6h 39m
1 stop
Delta Logo
3:50 pm - 10:07 pm
STT
-
GPT
8h 17m
1 stop
$657Delta
Sun, Oct 25 - Mon, Nov 9
Delta Logo
6:00 am - 1:39 pm
GPT
-
STT
6h 39m
1 stop
Delta Logo
3:50 pm - 10:07 pm
STT
-
GPT
8h 17m
1 stop
$675Delta
Booking Insights

KAYAK's insights & trends for Gulfport to Caribbean Islands flights

Get data-powered insights and trends into flights from Gulfport to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Gulfport to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $391, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonApril
Cheapest flight$161
Best time to beat the crowds with an average 3% drop in price.
Flight from Gulfport to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Gulfport to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Gulfport to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Gulfport to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Gulfport to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Gulfport to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Gulfport to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Gulfport to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Gulfport to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Gulfport to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Gulfport to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Gulfport to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11641 reviews
6.9Entertainment
6.4Food
7.2Comfort
7.5Boarding
7.9Crew
Airline reviews

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

8.0 ExcellentAnonymous, May 2026
RSW - ORD
Read more American Airlines reviews

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

Seat bottom cushions are not good. I’m 165# & they hurt my butt. Plenty of legroom.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Gulfport (GPT)