$99 Find Cheap Flights from Dallas 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 Dallas to Caribbean Islands departing on 11/18. 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 Dallas to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Dallas to Caribbean Islands.
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Cheap Flights from Dallas to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$427
Santo Domingo
Santo Domingo1 stop$299
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$273
Nassau
Nassau1 stop$396
Simpson Bay
Simpson Bay1 stop$323
Providenciales
Providenciales2 stops$493
George Town
George Town1 stop$389
Punta Cana
Punta Cana2 stops$427
Santo Domingo
Santo Domingo1 stop$299
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$273
Nassau
Nassau1 stop$396
Simpson Bay
Simpson Bay1 stop$323
Providenciales
Providenciales2 stops$493
George Town
George Town1 stop$389

Book Cheap Dallas 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 Dallas 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 Dallas to Caribbean Islands

Sun, Nov 9 - Sun, Nov 23
Frontier Logo
6:05 am - 1:32 amDFW-SJU
17h 27m2 stops
Frontier Logo
10:22 pm - 8:18 amSJU-DFW
11h 56m1 stop
$223Frontier
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Thu, Nov 27 - Thu, Dec 4
Multiple Airlines Logo
5:20 pm - 11:55 pmDFW-SJU
4h 35mnonstop
Multiple Airlines Logo
10:42 am - 6:09 pmSJU-DFW
9h 27m1 stop
$225Multiple Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
Spirit Airlines Logo
7:20 am - 11:18 pmDFW-SJU
13h 58m1 stop
Spirit Airlines Logo
5:28 pm - 8:55 pmSJU-DFW
5h 27mnonstop
$239Spirit Airlines
Find Deal
Thu, Jan 1 - Sun, Jan 11
Spirit Airlines Logo
5:45 am - 10:05 pmDFW-SJU
14h 20m1 stop
Spirit Airlines Logo
5:28 pm - 8:55 pmSJU-DFW
5h 27mnonstop
$240Spirit Airlines
Find Deal
Sun, Dec 7 - Wed, Dec 10
Southwest Logo
1:55 pm - 1:25 amDAL-SJU
9h 30m1 stop
Southwest Logo
6:40 am - 6:15 pmSJU-DAL
13h 35m1 stop
$273Southwest
Find Deal
Sun, Dec 7 - Wed, Dec 10
Southwest Logo
7:15 pm - 10:25 amDAL-SJU
13h 10m1 stop
Southwest Logo
11:20 am - 6:45 pmSJU-DAL
9h 25m2 stops
$298Southwest
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Sat, Dec 13 - Sat, Dec 20
American Airlines Logo
10:35 am - 3:35 pmDFW-PLS
4h 00mnonstop
American Airlines Logo
1:39 pm - 5:33 pmPLS-DFW
4h 54mnonstop
$518American Airlines
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Sat, Nov 29 - Sat, Dec 6
American Airlines Logo
6:00 am - 2:28 pmDFW-PLS
7h 28m1 stop
American Airlines Logo
1:19 pm - 5:10 pmPLS-DFW
4h 51mnonstop
$519American Airlines
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Sun, Dec 21 - Tue, Dec 23
Delta Logo
5:30 am - 12:45 pmDFW-PLS
6h 15m1 stop
Delta Logo
2:10 pm - 10:05 pmPLS-DFW
8h 55m1 stop
$532Delta
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Sun, Dec 7 - Sat, Dec 13
Delta Logo
5:19 am - 1:04 pmDFW-MBJ
6h 45m1 stop
Delta Logo
3:38 pm - 12:03 amMBJ-DFW
9h 25m1 stop
$560Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Dallas to Caribbean Islands flights

Get data-powered insights and trends into flights from Dallas to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Dallas to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Dallas found in the last 72 hours was to San Juan, at $193 round-trip. The most popular route is from Dallas/Fort Worth Airport (DFW) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $193.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Dallas 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 Dallas to Caribbean Islands is April, when tickets cost $309 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $413 and $401 respectively.

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

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

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Tuesday and more expensive on a Friday. On your return trip to Dallas, you should consider flying back on a Thursday, and avoid Sundays for better deals.

How far in advance should I book a flight from Dallas to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Dallas to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Dallas to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Cheapest flight$99
Flight from Dallas/Fort Worth Airport to Montego Bay

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Dallas 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 Dallas to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Dallas to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Dallas 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 Dallas 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 Dallas 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 Dallas 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 Dallas 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 $296 on average. Morning departures are around 20% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is $458.

Reviews of the top 5 airlines serving from Dallas to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Dallas 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 Dallas 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.
8.0
SouthwestOverall score based on 4242 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

The only thing to like was that we eventually got to our destination

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

We were delayed for a “couple of maintenance issues.” They were resolved rather quickly but a computer glitch caused someone in the airport to have to bring a physical copy of the paperwork so we could leave. I don’t know where they had to drive from to get to our plane but it took forever & we were 1 1/2 hrs late in leaving. The flight itself was fine.

We didn't take off until an hour after we boarded.

The flight was fine. This survey is not. There is no option for N/A so items which don’t apply to my experience still must be rated. In those instances I give a “3” rating which ultimately skews the results.

The actual trip was fine, however, the changes made to our flights and the layovers were had to endure were awful.

Flight from Dallas to OKC was good, but my trip was interrupted due to a delayed flight from Austin to DFW, which happens all the time. I frequently miss my connection from DFW and American can never seem to make this work!

Because the plane was 90 degrees F, they would not let us board. I wish they had, because it meant we were delayed. It's Texas, of course it's hot. We would have survived.

The Flight was fine, the staff treated me well, the flight got delayed over 5 1/2 hours for maintenance issues....but it worked out OK,, they were very apologetic about it, and it is better to not fly if there is any issue than endanger peoples lives, so in reality that was a good thing, It did cost me extra for parking because I went beyond the time I had purchased for parking at MSP. But all in all, Good flight

I did not take this flight because the reservation made by Kayak was wrong! Kayak owes me a trip from Minneapolis to Duluth.

When I got to the airport in Seattle, they told me the flight "did not exist". Kayak reserved me a seat on a flight that did not exist. This is inexcusable. I was able to change my reservation to a flight that actually did exist, but the flight was later and then I didn't make it in time for the next leg of my trip from Minneapolis to Duluth. Kayak owes me a trip from Minneapolis to Duluth, and a big apology for messing up my reservation.

The plane was freezing cold. Asked for a blanket and there were none. Was told twice that the pilots would warm the plane and it never happened Worst experience flying ever

Multiple delays because they screwed up on the crew schedule and had to wait for over an hour for more people to come.

The Wi-Fi was off, the arm rests are hard plastic.

The assistance with the wheel chairs was fabulous. All the people were so very friendly and helpful. I want to thank them all.

We almost missed our return flight. We got to the gate one minute from closing the cabin door, and the agent got us aboard the plane! We are so very grateful!!!!!

I already filled out a survey for this flight. We booked through KAYAK with airfare assist, and airfare assist did not confirm or honor our flight. Therefore, we had to go to a different place with a different travel agency. I tried very hard with airfare assist, They also promoted this on cheapair.com, but it was a bait and switch in both instances.

Boarded flight, issues with the place and had to get off the plane, wait, and then board a different plane at a different gate. This impacted my short trip negatively. A worker died outside of the plane window and we sat there the entire time while they tried to revive him, unsuccessfully, which was traumatic.

Always comes in handy when I want a quick weekend getaway.

The entire staff from check in agents to flight attendants were pleasant and professional. Would suggest a complimentary water.

Spirit is low fare air line. Food also cost you. No free food.

Everyone was kind for the most part. I did travel with children and paid for seats and even then it was not as suitable. I tried calling their customer service prior to check in and I was told they couldn't help me because I didn't purchase my tickets with them.

I think the staff was nice. They took time to explain safety protocols. Boarding was great. They started early and our flight left a little early which was convenient. Having free games to play would have been better

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

Better than my las vagas experience, but still dissapointed with the airline support service.

Unfortunately, spirits crew had us boarding and parking the plane often, would wait long periods of time before allowing the people attending the flight on the plane to know what was going on this caused for my plane to not only get diverted but then canceled at an airport 2 hours away and basically stranded with charter buses MAYBE being hired. I was left with no choice but to stay overnight and use a comp room in Altantic City to then arrive home the next day. This trip was the first time seeing my partner since he joined the Air Force and this stressful ride caused unwarranted tears on what was supposed to be an east flight home. I understand weather is unpredictable but to have passengers deboard to then reboard an hour later to taxi on the runway for another hour to then basically leave an entire fight stranded. I waited almost 30 minutes at the airport and not one employee could tell me about a charter bus so I had to leave and make accommodations to stay overnight and get a ride home.

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to Dallas

Cabin classes available on flights to Dallas. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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