$332 Find Cheap Flights from Midland to Caribbean Islands

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midland to Caribbean Islands departing on 9/20. 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

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 Midland to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Midland to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Midland to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Santo Domingo
Santo Domingo2 stops$475
Oranjestad
Oranjestad2 stops$600
Santo Domingo
Santo Domingo2 stops$475
Oranjestad
Oranjestad2 stops$600

Book Cheap Midland 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 Midland 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 Midland to Caribbean Islands

Sat, Sep 20 - Tue, Sep 23
American Airlines Logo
6:39 pm - 12:50 pmMAF-SJU
17h 11m2 stops
American Airlines Logo
6:10 am - 11:04 pmSJU-MAF
17h 54m2 stops
$332American Airlines
Find Deal
Mon, Aug 18 - Sat, Aug 23
United Airlines Logo
7:08 pm - 5:30 amMAF-SJU
9h 22m1 stop
United Airlines Logo
7:00 am - 2:02 pmSJU-MAF
8h 02m1 stop
$417United Airlines
Find Deal
Sat, Sep 20 - Tue, Sep 23
American Airlines Logo
6:01 am - 2:15 pmMAF-SJU
7h 14m1 stop
American Airlines Logo
6:10 am - 11:04 pmSJU-MAF
17h 54m2 stops
$420American Airlines
Find Deal
Mon, Aug 18 - Sat, Aug 23
American Airlines Logo
6:01 am - 2:25 pmMAF-SJU
7h 24m1 stop
American Airlines Logo
7:05 pm - 9:42 amSJU-MAF
15h 37m2 stops
$440American Airlines
Find Deal
Sat, Sep 20 - Tue, Sep 23
United Airlines Logo
9:46 am - 8:38 pmMAF-SJU
9h 52m1 stop
United Airlines Logo
2:55 pm - 9:55 pmSJU-MAF
8h 00m1 stop
$459United Airlines
Find Deal
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
$460American Airlines
Find Deal
Thu, Sep 18 - Mon, Sep 22
Delta Logo
5:21 pm - 1:24 pmMAF-SDQ
19h 03m2 stops
Delta Logo
7:40 pm - 11:53 amSDQ-MAF
17h 13m2 stops
$475Delta
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Fri, Nov 14 - Sat, Nov 22
Southwest Logo
11:45 am - 12:35 amMAF-SJU
10h 50m2 stops
Southwest Logo
5:55 pm - 12:25 amSJU-MAF
8h 30m1 stop
$499Southwest
Find Deal
Thu, Sep 18 - Mon, Sep 22
Delta Logo
5:21 pm - 1:24 pmMAF-SDQ
19h 03m2 stops
Delta Logo
7:40 pm - 11:53 amSDQ-MAF
17h 13m2 stops
$539Delta
Find Deal
Sat, Dec 20 - Sun, Dec 28
Southwest Logo
5:45 am - 6:20 pmMAF-SJU
10h 35m2 stops
Southwest Logo
5:35 am - 3:05 pmSJU-MAF
11h 30m2 stops
$1,105Southwest
Find Deal
Booking Insights

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

Get data-powered insights and trends into flights from Midland 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 Midland to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $520, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Midland 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 Midland to Caribbean Islands is January, when tickets cost $443 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $834 and $775 respectively.

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

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

For Midland to Caribbean Islands, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Caribbean Islands back to Midland, the best deals are generally found on Thursday, with Saturday being the most expensive.


Good to know

Low seasonNovember
Cheapest flight$332
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 35% increase in price.
Flight from Midland to San Juan

FAQs - booking Caribbean Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Midland 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 Midland 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 Midland 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 Midland 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 Midland 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 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 Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $919.

Reviews of the top airline flying from Midland to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Midland 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 Midland 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.
7.2
American AirlinesOverall score based on 10000 reviews
7.2Comfort
7.5Boarding
8.0Crew
6.9Entertainment
6.5Food
Airline reviews

Very poor delay in dfw was really bad n long

2.0 Mediocredavix, Jul 2025DFW - MKE
Read more American Airlines reviews

Very poor delay in dfw was really bad n long

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

Flight was delayed again and again ultimately almost three hours getting us to our location at close to midnight by the time we got in and out of airport to destination. I had taken time off work to enjoy an evening at destination and that was now wasted

The flight delay in Dallas created a domino effect that impacted all of the connecting flights. It also increased the number of connections. I missed my flight from Casablanca to Marrakech because of the tight turnaround when landing in Casablanca. . CMN airport was understaffed. Only one person could help while other employees were just watching him. It was an extremely frustrating situation. People were crying and slamming their palms on the counter when speaking to the customer service provider, Allabough (man’s name?). Allabough couldn’t change my flight in the system. simultaneously, I was on the call with America. Airlines customer service rep named Solomon that said he couldn’t change it either. So, I took a ONYA voyages train to from Casablanca to Marrakech to get there on Friday June 26. This was unpredictable trip.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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