$151 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 8/14. 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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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$528
Montego Bay
Montego Bay2 stops$357
Punta Cana
Punta Cana2 stops$528
Montego Bay
Montego Bay2 stops$357

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 29 - Thu, Jul 9
Multiple Airlines Logo
5:31 pm - 12:37 am
GPT
-
SJU
6h 06m
1 stop
Multiple Airlines Logo
5:22 pm - 7:41 am
SJU
-
GPT
15h 19m
1 stop
$340Multiple Airlines
Mon, Jun 29 - Wed, Jul 8
Multiple Airlines Logo
5:31 pm - 12:37 am
GPT
-
SJU
6h 06m
1 stop
Multiple Airlines Logo
6:31 pm - 7:10 pm
SJU
-
GPT
25h 39m
1 stop
$349Multiple Airlines
Thu, Jul 2 - Thu, Jul 9
Multiple Airlines Logo
7:50 pm - 7:55 am
GPT
-
SJU
11h 05m
1 stop
Multiple Airlines Logo
5:22 pm - 7:41 am
SJU
-
GPT
15h 19m
1 stop
$355Multiple Airlines
Sat, May 30 - Tue, Jun 2
American Airlines Logo
6:38 pm - 1:08 pm
GPT
-
MBJ
18h 30m
2 stops
American Airlines Logo
12:31 pm - 10:52 am
MBJ
-
GPT
22h 21m
2 stops
$357American Airlines
Sun, Jun 28 - Thu, Jul 9
Multiple Airlines Logo
7:50 pm - 1:16 pm
GPT
-
SJU
16h 26m
1 stop
Multiple Airlines Logo
5:22 pm - 7:41 am
SJU
-
GPT
15h 19m
1 stop
$359Multiple Airlines
Sun, Jul 5 - Thu, Jul 16
American Airlines Logo
5:14 am - 4:14 pm
GPT
-
MBJ
11h 00m
1 stop
American Airlines Logo
2:09 pm - 10:55 am
MBJ
-
GPT
20h 46m
2 stops
$477American Airlines
Wed, Jun 3 - Sat, Jun 6
United Airlines Logo
2:00 pm - 3:10 pm
GPT
-
MBJ
25h 10m
2 stops
United Airlines Logo
4:12 pm - 9:45 pm
MBJ
-
GPT
29h 33m
2 stops
$670United Airlines
Fri, Jun 5 - Sat, Jun 13
United Airlines Logo
5:19 pm - 5:00 pm
GPT
-
STT
22h 41m
2 stops
United Airlines Logo
6:05 pm - 9:45 pm
STT
-
GPT
28h 40m
2 stops
$954United Airlines
Sun, Sep 27 - Thu, Oct 1
Air Canada Logo
7:00 am - 11:30 am
GPT
-
GCM
28h 30m
2 stops
Air Canada Logo
12:25 pm - 7:40 pm
GCM
-
GPT
31h 15m
2 stops
$1,433Air Canada
Sun, Sep 27 - Thu, Oct 1
Air Canada Logo
2:00 pm - 11:30 am
GPT
-
GCM
21h 30m
2 stops
Air Canada Logo
12:25 pm - 4:11 pm
GCM
-
GPT
27h 46m
2 stops
$1,442Air 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 $345, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$151
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 3% increase 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 11668 reviews
7.5Boarding
7.9Crew
7.2Comfort
6.4Food
6.9Entertainment
Airline reviews

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

2.0 MediocreAnonymous, May 2026
ORD - LHR
Read more American Airlines reviews

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

The crew was very attentive through out the flight. Seats were comfortable, nice flight bag with pillow and blanket. Food was okay, since it was a overnight flight seemed to go by fast.

The flight attendant on my side of business class seemed like a novice and did not provide good service. Otherwise the flight was good and the entertainment system was very good. No free WiFi.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports