$257 Find Cheap Flights from Midland to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midland to Caribbean departing on 10/10. 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

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Best Caribbean Flight Deals from Midland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Oranjestad
Oranjestad2 stops$695
Oranjestad
Oranjestad2 stops$695

Cheap Flights from Midland to Caribbean

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midland to Caribbean 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 Midland to Caribbean

Tue, Sep 2 - Sat, Sep 6
American Airlines Logo
7:36 am - 11:59 pmMAF-SJU
15h 23m2 stops
American Airlines Logo
7:05 pm - 10:47 amSJU-MAF
16h 42m2 stops
$340American Airlines
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Mon, Aug 18 - Sat, Aug 23
American Airlines Logo
10:09 am - 11:59 pmMAF-SJU
12h 50m2 stops
American Airlines Logo
6:00 am - 6:03 pmSJU-MAF
13h 03m2 stops
$414American Airlines
Find Deal
Tue, Sep 2 - Sat, Sep 6
American Airlines Logo
5:00 am - 2:25 pmMAF-SJU
8h 25m1 stop
American Airlines Logo
3:05 pm - 11:04 pmSJU-MAF
8h 59m1 stop
$439American Airlines
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Mon, Aug 18 - Sat, Aug 23
American Airlines Logo
5:00 am - 2:25 pmMAF-SJU
8h 25m1 stop
American Airlines Logo
6:00 am - 7:45 pmSJU-MAF
14h 45m2 stops
$454American Airlines
Find Deal
Mon, Aug 18 - Sat, Aug 23
United Airlines Logo
5:30 pm - 5:30 amMAF-SJU
11h 00m1 stop
United Airlines Logo
7:00 am - 4:12 pmSJU-MAF
10h 12m1 stop
$455United Airlines
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Mon, Aug 18 - Sat, Aug 23
United Airlines Logo
1:58 pm - 5:30 amMAF-SJU
14h 32m2 stops
United Airlines Logo
7:00 am - 4:12 pmSJU-MAF
10h 12m1 stop
$465United Airlines
Find Deal
Mon, Aug 18 - Fri, Aug 22
United Airlines Logo
12:00 pm - 5:30 amMAF-SJU
16h 30m1 stop
United Airlines Logo
1:05 am - 2:02 pmSJU-MAF
13h 57m2 stops
$494United Airlines
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Tue, Jul 8 - Tue, Jul 15
Southwest Logo
7:45 am - 7:05 pmMAF-SJU
10h 20m2 stops
Southwest Logo
6:00 am - 1:55 pmSJU-MAF
8h 55m2 stops
$512Southwest
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Tue, Jul 8 - Tue, Jul 15
Southwest Logo
10:45 am - 10:25 pmMAF-SJU
10h 40m1 stop
Southwest Logo
6:00 am - 1:55 pmSJU-MAF
8h 55m2 stops
$526Southwest
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Mon, Aug 18 - Fri, Aug 22
 Logo
7:00 am - 6:20 pmMAF-SJU
10h 20m2 stops
 Logo
1:05 am - 9:55 pmSJU-MAF
21h 50m3 stops
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KAYAK's insights & trends for Midland to Caribbean flights

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

What is the cheapest month to fly from Midland to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Midland to Caribbean, 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 Midland to Caribbean is September, when tickets cost $422 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $834 and $818 respectively.

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

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

When flying from Midland to Caribbean, you should consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Midland, you’ll find the best rates on Thursdays and the most expensive ones on Saturdays.


Good to know

Low seasonNovember
High seasonDecember
Cheapest flight$257
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly with an average 36% increase in price.
Flight from Midland to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Midland to Caribbean?

    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 Midland to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Midland to Caribbean 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 Midland to Caribbean?

    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 Midland to Caribbean 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 Midland to Caribbean?

    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 Midland to Caribbean 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?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $570 on average. Morning departures are around 40% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $919.

Top 3 airlines serving from Midland to Caribbean

 
Need help choosing which airline to fly with from Midland to Caribbean? 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 4287 reviews
7.1Food
8.0Comfort
7.6Entertainment
8.2Boarding
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

My suitcase was completed destroyed. The top part is broken and unusable now.

We boarded but then sat there waiting on some missed connection people to get on so we sat for about 15 minutes for that. Then we sat again because the passenger manifest was wrong and they had to figure it out before we could leave. That took about another 20 minutes or so. The crew was working hard to figure it out so it’s not their fault. It ended up being a system glitch where someone was upgraded to first class while another person was also in the same seat and it just created a mess that took a little while to figure out. They literally went to every person on the plane asking their names to see who was sitting in the wrong seat. I also hate the entertainment that must be watched on your phone or tablet. Just give us setback screens. It’s so much better. Almost every Delta flight has this now and it is so nice to have them. The crew did a great job. I have no complaints from them. They were very hard working, even with the mishap and a disgruntled passenger.

My priority checked bag was not loaded on the flight. I had to sit in baggage claim in Las Vegas for 2 1/2 hours waiting for the next flight. All baggage staff were very helpful, tracking showed it as scanned for loading. Nobody told me why it wasn't on my flight.

All male crew was just too woke for me. I felt like a sardine. I will never take a window seat or the rearmost seat again. I booked early and did not pay for seat selection and that was a mistake. The security at IAH was atrocious. I was violated and radiated as I was in a hurry to connect to my other flight. I may have lost items under the seat in front of me that I couldn't see nor bend over to look.

Food choices were very limited. Taste of the dishes was average.

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

Oh my gosh, I loved my experience with United! they made me want to travel more often.

In general ok, my only issue is that they had no hot items for purchase. I had very little time in my connection due to baggage/customs/TSA, thag I barely even had a chance for a stop at the washroom and buy water, to make it to my gate when they started boarding. I had nothing to eat because the trip started early, so I was ready to purchase, and they had nothing except for dry items like snacks. I had to purchase a mediocre, overpriced cheese and fruit board, instead of at least a pizza or sliders that I was planning on getting. Other than that, it was fine. But that’s typical Air Canada, to not have enough.

How badly can you screw up baggage claim? We were told to go to baggage claim too for our bags from this flight. Another flights bags were there. They finished up. More bags from a different flight arrived. Our bags did not Finally the baggage claim belt stopped working and and are flight was still listed on the arrivals for that baggage claim 2. And then nothing It turns out that they had been delivered not only the United baggage claim but far away on a Delta baggage claim No I never told us. It was only the people looking around who had been on the flight But I’m sure there was plenty of time for the employees to raffle through the bags and steal whatever they wanted

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

At the beginning of the flight there was some turbulence and the announcement was made that there would be no beverage service. The turbulence only last about 5 minutes then it was smooth sailing. I noticed that first class got their service, but the rest of us did not.

Update departure times in a more timely manner. We are not boarding on time if the plane isn’t arriving until after our scheduled departure time.

Update.us on flight information in a more timely manner. Don’t say we are boarding on time ten minutes before the boarding time when the aircraft isn’t arriving for another forty minutes.

Took off on time and successfully avoided weather that looked to be a problem along the way

I liked everything. Except that my neck was hurting on the seat. I couldn't sleep.

We were delayed Al ost / hours after boarding so that maintenance had to add oil to the engines. Then the oil they grabbed had been left out in the Dallas record cold and was frozen. They had to go back to the hanger and grab some that was not frozen.

They changed my seat from one that I had paid for as an upgrade to a regular seat at the last minute.

Flight was empty so had a whole row to myself. Still had to wait to get the bag due to the negligence at Palm Springs departure.

Everything was on time, we arrived early, everything worked well.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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