Find cheap flights from Gulfport to Caribbean Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Gulfport to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana2 stops$591
Montego Bay
Montego Bay2 stops$823
Punta Cana
Punta Cana2 stops$591
Montego Bay
Montego Bay2 stops$823
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?

No, with an average price for the route of $376, prices are generally cheapest when you fly direct.

Good to know

Low season

September
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 30% lower on average.

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

 
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.
7.0
American AirlinesOverall score based on 12073 reviews
7.2Comfort
6.8Entertainment
6.4Food
7.4Boarding
7.9Crew
Airline reviews

Flight was delayed significantly at take off and landing. Confusion of gate assignment with back and forth. Overall, makes for a very unpleasant experience that appears to come down to inept operational management.

2.0 MediocreSamantha, Sep 2026
Read more American Airlines reviews

Flight was delayed significantly at take off and landing. Confusion of gate assignment with back and forth. Overall, makes for a very unpleasant experience that appears to come down to inept operational management.

My experience was excellent for a business trip. I like the smaller jets because everyone gets either a window or aisle seat and the boarding and de-planing goes much faster. I really like the schedule American Airlines has between Atlanta and NY - lots of options. Crews are great and very accommodating. Sometimes the flights are not full and they let people move around once the boarding doors are shut to spread out.

It was delayed a lot longer than 10 minutes because we arrived 45 minutes beyond our original arrival time. We sat on the tarmac waiting to take off for a very long time. The seats and entertainment options on American were not good and very limited. The ability to text via WiFi for free was nice, but that seems to be standard on mainline flights. Also, gold status really does not do anything for you anymore.

Primary flight attendant in FC wasn't that engaged throughout the flight. All other aspects of flight were good.

We waited over 30 minutes for a gate in Chicago and more than 15 minutes for the doors to open. Cookies were missing from the menu.

On-time, direct flight is great. Having one bathroom out of order was unfortunate.

I sat in seat 22D near the back right of the plane. My phone battery was getting low, so I plugged my charger into the power outlets below the seats in front of me. They did not work. When I asked the flight attendant whether this was the case for the whole plane he said, "No. It's only this one. It hasn't worked for months". This should be noted to whomever services this plane so that maintenance can fix this for future passengers. I was on Flight AA5614 from Grand Rapids to Philadelphia on Wednesday, September 23, 2026.

The crew was wonderful, the plane was fine. We left the gate on time, but we had to wait 40 minutes on the tarmac because of all the congestion at Boston.

Seats were the worst i ever experienced — narrow, hard, no leg room and a long flight

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.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental