$289 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 9/4. 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

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$658
Montego Bay
Montego Bay1 stop$566
Bridgetown
Bridgetown2 stops$586
Punta Cana
Punta Cana2 stops$658
Montego Bay
Montego Bay1 stop$566
Bridgetown
Bridgetown2 stops$586

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

Sun, Feb 22 - Thu, Feb 26
Delta Logo
10:30 am - 8:30 pmGPT-SJU
8h 00m1 stop
Delta Logo
6:15 am - 1:37 pmSJU-GPT
9h 22m1 stop
$438Delta
Find Deal
Sun, Feb 22 - Thu, Feb 26
Delta Logo
10:30 am - 8:30 pmGPT-SJU
8h 00m1 stop
Delta Logo
6:15 am - 1:37 pmSJU-GPT
9h 22m1 stop
$453Delta
Find Deal
Sun, Feb 22 - Wed, Feb 25
United Airlines Logo
7:15 am - 12:36 amGPT-SJU
15h 21m2 stops
United Airlines Logo
2:05 am - 4:02 pmSJU-GPT
15h 57m2 stops
$455United Airlines
Find Deal
Sun, Feb 22 - Thu, Feb 26
Delta Logo
10:30 am - 8:30 pmGPT-SJU
8h 00m1 stop
Delta Logo
6:15 am - 1:37 pmSJU-GPT
9h 22m1 stop
$463Delta
Find Deal
Sun, Feb 22 - Wed, Feb 25
United Airlines Logo
7:15 am - 4:36 pmGPT-SJU
7h 21m1 stop
United Airlines Logo
2:05 am - 4:02 pmSJU-GPT
15h 57m2 stops
$475United Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
American Airlines Logo
6:18 pm - 12:00 pmGPT-STT
16h 42m1 stop
American Airlines Logo
5:20 pm - 5:32 pmSTT-GPT
25h 12m2 stops
$479American Airlines
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Wed, Oct 15 - Mon, Oct 20
American Airlines Logo
5:45 pm - 12:49 pmGPT-STT
18h 04m2 stops
American Airlines Logo
5:20 pm - 12:45 pmSTT-GPT
20h 25m2 stops
$499American Airlines
Find Deal
Sun, Feb 22 - Thu, Feb 26
American Airlines Logo
6:52 pm - 11:45 amGPT-SJU
14h 53m1 stop
American Airlines Logo
5:41 am - 10:15 pmSJU-GPT
18h 34m2 stops
$514American Airlines
Find Deal
Wed, Sep 24 - Wed, Oct 1
 Logo
4:44 pm - 9:25 amGPT-ANU
39h 41m2 stops
 Logo
12:15 pm - 4:12 pmANU-GPT
28h 57m3 stops
$1,480
Find Deal
Wed, Sep 24 - Wed, Oct 1
 Logo
7:05 am - 11:00 amGPT-ANU
26h 55m3 stops
 Logo
12:15 pm - 4:12 pmANU-GPT
28h 57m3 stops
$1,668
Find Deal
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 $421, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Gulfport to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Gulfport to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Gulfport to Caribbean Islands is January, when tickets cost $379 (return) on average. On the other hand, the most expensive months are August and March, when the average cost of round-trip tickets is $909 and $877 respectively.

What’s the cheapest day of the week to fly from Gulfport to Caribbean Islands?

The average price of all round-trip flights from Gulfport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

For Gulfport to Caribbean Islands, Monday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Caribbean Islands back to Gulfport, the best deals are generally found on Tuesday, with Thursday being the most expensive.

Good to know

Low seasonNovember
Cheapest flight$289
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 21% lower on average.
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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $380 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $589.

Reviews of the top airlines 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.
7.9
DeltaOverall score based on 7977 reviews
8.2Boarding
8.5Crew
7.3Food
7.9Entertainment
7.9Comfort
Airline reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

4.0 Okaypuravi, Aug 2025LGA - STL
Read more Delta reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

The flight was canceled 3 hours after original take off time

My flight was delayed for several hours. Sitting at gate 16 for several hours, I got a text from Kayak the gate changed to 9 before it was announced. Very bad communication at each gate from American Airlines employees. I received 10 notifications of delay from Kayak. My vacation started off horrible! I will write to American Airlines corporate office also.

The AA staff person who checked our bags was curt and almost rude. The FA also seemed unhappy doing her job. Overall it was like riding the school bus back in grade school.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Ring in first class for an overnight flight, there was no blankets nor pillows for first class customers.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

Delayed flight that lead to a missed connection and a 5-hour trip became a 12-hour flight 🙄

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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