$203 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 8/1. 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 Cana2 stops$588
Montego Bay
Montego Bay2 stops$447
Bridgetown
Bridgetown2 stops$856
Punta Cana
Punta Cana2 stops$588
Montego Bay
Montego Bay2 stops$447
Bridgetown
Bridgetown2 stops$856

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

Fri, Aug 14 - Sat, Aug 22
Multiple Airlines Logo
5:31 pm - 12:41 am
GPT
-
SJU
6h 10m
1 stop
Multiple Airlines Logo
6:35 am - 7:41 am
SJU
-
GPT
50h 06m
2 stops
$289Multiple Airlines
Fri, Aug 14 - Sat, Aug 22
Multiple Airlines Logo
5:31 pm - 12:41 am
GPT
-
SJU
6h 10m
1 stop
Multiple Airlines Logo
8:57 pm - 6:45 pm
SJU
-
GPT
22h 48m
1 stop
$348Multiple Airlines
Tue, Nov 10 - Tue, Nov 17
American Airlines Logo
7:30 pm - 4:55 pm
GPT
-
STT
19h 25m
2 stops
American Airlines Logo
4:18 pm - 12:23 pm
STT
-
GPT
22h 05m
2 stops
$398American Airlines
Mon, Sep 21 - Tue, Sep 29
American Airlines Logo
5:35 am - 2:45 pm
GPT
-
SJU
8h 10m
1 stop
American Airlines Logo
11:51 am - 10:32 pm
SJU
-
GPT
11h 41m
2 stops
$446American Airlines
Mon, Aug 31 - Thu, Sep 3
United Airlines Logo
7:08 am - 3:42 pm
GPT
-
SJU
7h 34m
1 stop
United Airlines Logo
7:00 am - 4:12 pm
SJU
-
GPT
10h 12m
1 stop
$676United Airlines
Mon, Aug 24 - Thu, Aug 27
United Airlines Logo
4:59 pm - 12:40 pm
GPT
-
PUJ
18h 41m
2 stops
United Airlines Logo
3:35 pm - 7:38 pm
PUJ
-
GPT
53h 03m
2 stops
$741United Airlines
Fri, Jul 10 - Tue, Jul 14
Delta Logo
6:30 am - 11:31 am
GPT
-
GCM
5h 01m
1 stop
Delta Logo
12:56 pm - 10:14 pm
GCM
-
GPT
9h 18m
1 stop
$786Delta
Sun, Jul 12 - Thu, Jul 16
Delta Logo
6:30 am - 2:23 pm
GPT
-
STT
6h 53m
1 stop
Delta Logo
3:33 pm - 10:14 pm
STT
-
GPT
7h 41m
1 stop
$1,117Delta
Sun, Dec 6 - Thu, Dec 10
Air Canada Logo
7:00 am - 2:35 pm
GPT
-
BGI
29h 35m
2 stops
Air Canada Logo
4:05 pm - 9:27 pm
BGI
-
GPT
31h 22m
2 stops
$1,409Air Canada
Mon, Dec 7 - Fri, Dec 11
Air Canada Logo
7:00 am - 2:35 pm
GPT
-
BGI
29h 35m
2 stops
Air Canada Logo
4:05 pm - 9:27 pm
BGI
-
GPT
31h 22m
2 stops
$1,446Air Canada
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 $381, prices are generally cheapest when you fly direct.

Good to know

Low seasonApril
Cheapest flight$203
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 28% lower on average.
Flight from Gulfport to Montego Bay

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 11766 reviews
7.5Boarding
7.2Comfort
6.8Entertainment
7.9Crew
6.4Food
Airline reviews

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

2.0 MediocreKrishna, Jun 2026
MHT - ORD
Read more American Airlines reviews

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

Entertainment system did not function. USB ports did not function. Wi-Fi did not function. Terrible trifecta…

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

My flight was delayed twice. The first time because of “plane maintenance” and the second because the previous flight who supposedly “arrived early” took an obnoxiously long time to get off the plane. Total delay was over an hour for no reason. Not to mention your airline repeatedly changed our gate from one end of the terminal to the other. Not very happy about this experience. My previous flights with American haven’t had this many issues.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

We’ve had a year of delays with American, and this one was another flight to add to that list. It just reduced our vacation by a day! So frustrating. In-flight entertainment (TVs) weren’t working, There was no drinks service due to delivery issues.

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

2 hours delay on my flight causing me to miss my connecting flight. Cause was for maintenance. I understand maintenance is important but maintenance should be done before boarding people!

Better perks for corporate employees whom travel often and spend a lot of money with the airlines. Snacks were terrible chips crackers are ideas. Flight and crew were great comfort was fine entertainment not so great so so called status members means nothing

American Airlines gets worse every time I fly them. This is the 3rd time they lost my bags in a year. I also think their employees do not care when I communicate that I’m unsatisfied with the airlines. I’m a credit card holder, fly first class, and an advantage member but I think that I’m finally going to make the switch to Delta.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports