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Caribbean Islands

$165+ Cheap flights from Midland (MAF) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
dic. 4 — dic. 111
jue. 12/4
jue. 12/11
1 adult, Economy
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Find flight deals from Midland to Caribbean Islands

Cheapest flights from Midland to Caribbean Islands
Explore the most affordable flight options available from Midland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 4, 2025.

This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/26:52 pmMAF - SJU
2 stops15h 07mAmerican Airlines
mar. 12/166:42 pmSJU - MAF
2 stops15h 56mAmerican Airlines
Deal found 11/3$490
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/212:03 pmMAF - SJU
1 stop7h 23mUnited Airlines
mié. 12/103:46 pmSJU - MAF
1 stop9h 27mUnited Airlines
Deal found 11/2$532
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/187:56 amMAF - SJU
2 stops14h 40mUnited Airlines
jue. 11/202:05 amSJU - MAF
2 stops13h 52mUnited Airlines
Deal found 11/4$575
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/25:00 amMAF - SJU
1 stop9h 36mUnited Airlines
lun. 12/152:05 amSJU - MAF
2 stops21h 54mUnited Airlines
Deal found 11/3$742
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/208:28 pmMAF - SDQ
2 stops17h 21mAmerican Airlines
sáb. 1/106:00 amSDQ - MAF
2 stops18h 54mAmerican Airlines
Deal found 11/3$1,044
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/257:00 amMAF - SJU
1 stop12h 26mUnited Airlines
dom. 11/307:45 amSJU - MAF
1 stop8h 12mUnited Airlines
Deal found 11/3$1,252
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/293:45 pmMAF - SJU
1 stop12h 26mUnited Airlines
dom. 1/47:45 amSJU - MAF
1 stop12h 34mUnited Airlines
Deal found 11/3$1,352

Cheap flight deals from Midland to Caribbean Islands

Keep the following information in mind while searching for Midland to Caribbean Islands flight deals. Data was last updated noviembre 4, 2025.

Round-trip from

$490
(American Airlines)

One-way from

$165
(United Airlines)

Popular in

July

Cheapest in

April

Average price

$603
From Midland Intl to Caribbean Islands
Search Deals
One-way flight from Midland Intl to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midland to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated noviembre 4, 2025.
Use the filters below to find and compare flights from Midland to Caribbean Islands that are best for you.

Fly from

Midland

Fly to

Caribbean Islands

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

mar. 12/2

6:52 pm-11:59 am

2 stops15h 07m

San Juan Luis Munoz Marin Intl

mar. 12/16

6:42 pm-8:38 am

2 stops15h 56m

$490

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

mar. 12/2

6:52 pm-10:09 am

2 stops13h 17m

San Juan Luis Munoz Marin Intl

mié. 12/10

7:00 am-1:59 pm

1 stop8h 59m

$490

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

mar. 12/2

12:03 pm-9:26 pm

1 stop7h 23m

San Juan Luis Munoz Marin Intl

mié. 12/10

3:46 pm-11:13 pm

1 stop9h 27m

$532

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

mar. 3/10

7:20 am-11:36 pm

2 stops15h 16m

San Juan Luis Munoz Marin Intl

mié. 3/11

4:50 pm-1:39 pm

2 stops21h 49m

$567

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

mar. 11/18

12:05 pm-9:26 pm

1 stop7h 21m

San Juan Luis Munoz Marin Intl

jue. 11/20

2:05 am-1:57 pm

2 stops13h 52m

$575

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

mar. 3/10

8:33 pm-3:55 am

1 stop6h 22m

San Juan Luis Munoz Marin Intl

mié. 3/11

9:26 am-11:45 pm

2 stops15h 19m

$597

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

mar. 3/10

5:59 am-1:44 pm

1 stop7h 45m

Montego Bay Sangster Intl

mié. 3/11

5:00 pm-10:28 pm

2 stops29h 28m

$656

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

mar. 3/10

5:00 am-1:05 pm

1 stop8h 05m

Montego Bay Sangster Intl

mié. 3/11

2:20 pm-1:39 pm

1 stop23h 19m

$661

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

lun. 4/6

4:55 pm-11:55 am

2 stops18h 00m

Santo Domingo Las Americas

mié. 4/8

1:10 pm-8:45 am

2 stops20h 35m

$672

MidlandSimpson Bay

MAF - SXM

MAFSXM

Midland Intl

lun. 4/6

6:43 pm-3:15 pm

2 stops19h 32m

Simpson Bay Princess Juliana

jue. 4/9

5:25 pm-1:56 pm

2 stops21h 31m

$720

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 22 results
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Best time to book a flight from Midland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Midland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Midland to Caribbean Islands

What is the cheapest month to book a flight from Midland to Caribbean Islands?

Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean Islands (average of $247). Flying from Midland to Caribbean Islands in July is currently the most expensive (average of $666). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MAF to EPX?

Find hourly flight availability from Midland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated noviembre 4, 2025.

When flying from Midland to Caribbean Islands, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 23% versus a flight at noon.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated noviembre 4, 2025.
Read through reviews of airlines operating flights from Midland to Caribbean Islands, such as American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,040 reviews

Boarding

7.5

Overall

7.2

Comfort

7.2

Entertainment

6.9

Crew

8.0

Food

6.4

Reviews

1 / 20
6.0
Good

sheila,Mar 2025

DFW - MSP

We were delayed for 3 hours with no real reason or offer for compensation
American Airlines
7.2
Good
11,040 reviews
American Airlines
7.2
Good
11,040 reviews

Boarding

7.5

Overall

7.2

Comfort

7.2

Entertainment

6.9

Crew

8.0

Food

6.4

Reviews

1 / 20
6.0
Good

sheila,Mar 2025

DFW - MSP

We were delayed for 3 hours with no real reason or offer for compensation

Related info for your journey

Find useful and relevant information for your journey from Midland to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Midland to Caribbean Islands?

    Midland Intl (MAF), located 8.2 mi from the city center, is the airport you fly out of when you book flights from Midland to Caribbean Islands.

  • How long is the flight from Midland to Caribbean Islands?

    There are many flights that can get you from Midland to Caribbean Islands in 7h 23m. Fly via American Airlines or United Airlines to get the fastest option. Airlines will cover a distance of 2432 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Midland to Caribbean Islands one-way?

    $165 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $190 and $223, respectively.

  • What are the most popular routes from Midland to Caribbean Islands?

    When deciding which route to take from Midland to Caribbean Islands consider Midland Intl - San Juan Luis Munoz Marin Intl, Midland Intl - Santo Domingo Las Americas or Midland Intl - Oranjestad Reina Beatrix as they are the most popular.

  • Can I find deals for flights from Midland to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Midland to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midland to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Caribbean Islands.

  • Can I find deals for business class flights from Midland to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Midland to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Midland to Caribbean Islands?

    Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean Islands (average of $247). Flying from Midland to Caribbean Islands in July is currently the most expensive (average of $666). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Midland to Caribbean Islands

Discover the top 3 airlines that operate flights from Midland to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated noviembre 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$370Average$544FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$380Average$915FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$513Average$544FlexibilityNo cancel feeOn-time63%

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