$215 Find Cheap Flights from Midland to Caribbean - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Midland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Montego Bay
Montego Bay1 stop$453
Montego Bay
Montego Bay1 stop$453
Booking Insights

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?

The cheapest month for flights from Midland to Caribbean is October, when tickets cost $430 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $1,099 and $825 respectively.

Good to know

Low season

November

Cheapest flight

$215
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 17% lower on average.
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.

Reviews of the top airlines flying 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.
7.9
SouthwestOverall score based on 4220 reviews
7.0Food
8.0Comfort
8.6Crew
7.4Entertainment
8.1Boarding
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.

My experience was okay I changed my returning flight and I was charged extra money which I dont think should be the case, especially because I experienced small delays from my going flight. And many flights were either canceled or delayed after my original flight time. I believe some customers should have the ability to change flights due to certain situations

It’s too cold like fridge and they don’t offer a blanket with expensive price

You made me miss my connecting flight. I can not go to Cleveland on teh revised flight you are sending as I will the entire meeting. I have no option that to fly back. I hope you compensate me for the loss.

Horrible communication from Southwest. No accountability. Flight was delayed for 4 hours and TSA closed in the interim. We were not allowed to our gate. Southwest knew this information and did not relay to their customers to arrive to the airport earlier.

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.

One, we were met with more than six hours of delays with no information flowing from the airline to the passenger. I had to continually refresh for updates to departure time - which changed multiple times throughout the day. Updates were never pushed to me nor was an explanation provided for the delay until this morning. Two, while they claim that "due to the short flight" no beverage service would be provided. Our flight was mostly empty. I'd think given the massive inconvenience, SW could have shared a Diet Coke and some peanuts. And BTW, SW used to always make these available on this flight back in the day. Let's be honest, this is cost savings at the customer's expense.

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.

No wifi, seems to be very common with Southwest currently. Everything else was normal.

It was great. I really love the app. User friendly and very comprehensive when it comes to having information at my fingertips tips related my travel.

Seat would not recline, and charger did not work. Person in front of me reclined before we took off and left it reclined when they got off the plane. Nobody ever told them to put their seat in upright position....which meant I was somewhat trapped in my window seat when deplaning. Another passenger had to go to their seat and un-recline so I could get out.

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.

- delayed because video screens not working - delayed getting a gate at DCA Just continued bad experience IAH to DCA.

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

I couldn’t give an honest evaluation, because the Houston airport has a problem and I was stand up for several hours and after a long trip from Munich I feel really very tired

The experience was good overall; however, my United Airlines Mileage Plus Account didn't reflect my flights to Houston from Newark. In essence, my mileage rewards points do not reflect my actual travel. This should be corrected.

Good flight, even though there was a delay, still got back on time

First class flight crew was barely available. They came through 3 times while we were on the plane for nearly 4 hours.

More options for your flight to Caribbean

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