$187 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 5/10. 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$571
Montego Bay
Montego Bay2 stops$477
Punta Cana
Punta Cana2 stops$571
Montego Bay
Montego Bay2 stops$477

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

Mon, Jun 15 - Sat, Jun 20
Multiple Airlines Logo
5:31 pm - 12:37 am
GPT
-
SJU
6h 06m
1 stop
Multiple Airlines Logo
8:50 am - 7:10 pm
SJU
-
GPT
35h 20m
2 stops
$419Multiple Airlines
Sun, Jun 14 - Sat, Jun 20
Multiple Airlines Logo
7:50 pm - 7:55 am
GPT
-
SJU
11h 05m
1 stop
Multiple Airlines Logo
8:50 am - 7:10 pm
SJU
-
GPT
35h 20m
2 stops
$436Multiple Airlines
Mon, Jun 15 - Thu, Jun 18
Multiple Airlines Logo
5:31 pm - 12:37 am
GPT
-
SJU
6h 06m
1 stop
Multiple Airlines Logo
8:00 am - 7:10 pm
SJU
-
GPT
12h 10m
2 stops
$444Multiple Airlines
Mon, Jun 15 - Thu, Jun 18
Multiple Airlines Logo
5:31 pm - 12:37 am
GPT
-
SJU
6h 06m
1 stop
Multiple Airlines Logo
6:00 am - 7:10 pm
SJU
-
GPT
14h 10m
1 stop
$445Multiple Airlines
Sun, Jun 14 - Thu, Jun 18
Multiple Airlines Logo
7:50 pm - 5:33 pm
GPT
-
SJU
20h 43m
2 stops
Multiple Airlines Logo
6:00 am - 7:10 pm
SJU
-
GPT
14h 10m
1 stop
$453Multiple Airlines
Sat, Jun 27 - Wed, Jul 1
American Airlines Logo
6:38 pm - 11:44 am
GPT
-
MBJ
17h 06m
2 stops
American Airlines Logo
5:17 pm - 10:11 am
MBJ
-
GPT
16h 54m
2 stops
$477American Airlines
Mon, Jul 13 - Mon, Jul 20
American Airlines Logo
6:32 pm - 4:00 pm
GPT
-
STT
20h 28m
2 stops
American Airlines Logo
1:42 pm - 10:11 am
STT
-
GPT
21h 29m
2 stops
$550American Airlines
Wed, Aug 12 - Wed, Aug 19
Delta Logo
6:00 am - 2:51 pm
GPT
-
PUJ
7h 51m
1 stop
Delta Logo
4:16 pm - 10:06 pm
PUJ
-
GPT
6h 50m
1 stop
$611Delta
Tue, Jul 14 - Tue, Jul 21
United Airlines Logo
7:00 am - 1:30 pm
GPT
-
MBJ
6h 30m
1 stop
United Airlines Logo
4:12 pm - 4:11 pm
MBJ
-
GPT
23h 59m
2 stops
$916United Airlines
Tue, Jul 14 - Tue, Jul 21
United Airlines Logo
7:00 am - 1:30 pm
GPT
-
MBJ
6h 30m
1 stop
United Airlines Logo
2:40 pm - 4:11 pm
MBJ
-
GPT
25h 31m
1 stop
$923United Airlines
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 $431, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$187
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 2% increase in price.
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 11681 reviews
7.5Boarding
7.9Crew
7.2Comfort
6.4Food
6.9Entertainment
Airline reviews

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

2.0 MediocreYovana, Apr 2026
BWI - DFW
Read more American Airlines reviews

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

On time departure and early arrival. Flight attendant very nice.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports