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Cheap Flights from Dallas to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana2 stops$644
Santo Domingo
Santo Domingo2 stops$344
Montego Bay
Montego Bay1 stop$307
Oranjestad
Oranjestad2 stops$413
Nassau
Nassau1 stop$316
Providenciales
Providenciales1 stop$437
George Town
George Town1 stop$443
Punta Cana
Punta Cana2 stops$644
Santo Domingo
Santo Domingo2 stops$344
Montego Bay
Montego Bay1 stop$307
Oranjestad
Oranjestad2 stops$413
Nassau
Nassau1 stop$316
Providenciales
Providenciales1 stop$437
George Town
George Town1 stop$443
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?

The cheapest ticket to Caribbean Islands from Dallas found in the last 5 days was to San Juan, at $394 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 5 days was $394.

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

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $482 on average. Morning departures are around 3% more expensive than evening flights, 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 $595.

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

The cheapest month for flights from Dallas to Caribbean Islands is February, when tickets cost $577 (return) on average. On the other hand, the most expensive months are October and November, when the average cost of round-trip tickets is $800 and $783 respectively.

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

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Monday and more expensive on a Wednesday. 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 get a below average price on the flight from Dallas to Caribbean Islands, you should book around 3 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

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.

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

 
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.
7.9
SouthwestOverall score based on 4217 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.4Entertainment
Airline reviews

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

6.0 GoodDanielle, Oct 2026
Read more Southwest reviews

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

I got a bit sick on the flight, and was so grateful when the male flight attendant explained to me they keep the back row open for cases like mine. He took such great care of me! I was incredibly grateful.

I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.

Unfortunately, I left my headphone's case in the bag of the front seat. I was seating on 9C. Hopefully the found it and I can get it back. I have not been able to get in contact with Southwest. Other than that, everything went fine.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

I don't know why flying out of Sarasota requires two plane changes.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I elected to pay for the upgrades and found very little difference

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

Everything was great except the fact that catering did not restock the flight from ATL to GRB and we were only offered water.

The WiFi on the plane was out. I also thought movie options were lacking.

These Delta 717 jets are ancient. No entertainment and you have to pay for WiFi that barely works and goes in and out the whole flight. Delta should be ashamed flying this garbage.

My seat was changed without my consent. It wasn’t a major deal but annoying.

It was delayed over an hour and a lot of announcements disrupting movie.

Delta has joint the nickel and diming airlines. The experience is getting worst by the day. 1,000,000 miles for a trip to Asia in Business Class where I got the same thing for just under 90,000 miles through an Asian airline. Where is Richard Anderson? Please come back!

I had an extensive delay on my previous flight and we had another delay due to the crew not being there. We were scheduled to have a late arrival but due to the delay it was even longer.

No tv. No free wifi. They need to ipgrade these planes - especially on a 2 hour flight.

I am a die hard Delta flyer, but they missed it on this flight. It was on their very dated 717-200 aircraft, which I knew when I booked it so I knew it wouldn’t have seatback screens. However, the internet was awful and it wouldn’t even send texts a lot of the time, much less even connect to the delta app. It was also very hot while in the air, which never happens. What was even more disappointing is that the crew only gave me cheezits and a beverage, even though I was in Delta Comfort. The main cabin fare gets these items. I didn’t get any kind of improved snacks and that was unacceptable. The crew wasn’t very visible at all either. If this was my first delta flight, it would be my last. I am just going to assume it was a one-off flight.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Bathrooms broken, Wifi not working, Direct TV stuck in a United credit card loop for whole flight

Flight was so congested it was disgusting. Hals of the hostesses clearly seemed to be racist. no sanitation maintained in the restrooms.

The WiFi went out an hour before the flight was due to land so I did not get my money's worth.

Bag got checked but I thought one personal item was guaranteed.

It was terribly delayed with zero support from united airlines. I reached at 1 am in the night. They did not provide any option to change the flights.

Flight cancelled instead of leaving Friday am now, maybe, leaving Sunday

one of the flight attendants on the Dallas to frankfurt leg was somewhat rude..

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

A little bit more leg room in premium economy. I am 6’4”.

Sucks ! All three flights I was on this trip were delayed.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

The flight left unexpectedly early. Although I checked in at the gate, the crew made no attempt to contact me to inform me that what had been a delayed flight was now departing before the scheduled departure time. No announcement on the PA, no phone call. When I checked back at the gate for the delay status just before the scheduled departure time, I was told the doors were already locked and the flight had left.

The wifi didn't work and I needed to do some work. This was a business trip.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

awful delay, awful communication, zero updates throughout the experience of a giant delay

On Time. AA is late due to maintenance all the time.

Flight attendants were pleasant and helpful. Pilot gave fair warning about turbulence.

Unfortunately the flight was delayed. On a positive note the status updates in the app/text message were good

We waitied for 2 hours for flights to take off. Make us to seat 2 hours in small space is not good.

Wheel Chair Access sucked. I had a guy from Bangaldesh drop me off without taking me to the gate

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

extremely tight seats. seating next to a large person makes the space very uncomfortable. The crew is not very friendly either.

The flight was 3 hours and 40 minutes late. The communication around the delays was awful. I fly this route regularly and it is always late. I don't understand it. The flight attendants were not friendly and were generally loud. This was an overall bad look for American Airlines.

Very Good in general. Serving attitude are very good. Just a suggestion: There 2 things can be improved: 1. The flight attendants can lower the voices when they talked in the serving station. Sometimes they talked loud and we could hear clearly what they said about the passengers. 2. Please don’t throw the utensils and plates it’s too loud and noisy. They broke the glasses and plates sometimes at the business class. These all could be done in a gentle way. Just some small observations. Thanks.

More options for your flight to Caribbean Islands

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