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Caribbean Islands

$194+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Feb 10 — Feb 171
Tue 2/10
Tue 2/17
1 adult, Economy
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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 January 11, 2026.

Round-trip from

$240
(American Airlines)

One-way from

$194
(American Airlines)

Popular in

July

Cheapest in

April

Average price

$480
From Midland Intl to Caribbean Islands
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One-way flight from Midland Intl to Caribbean Islands
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Highest demand for flights based on searches. 6% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 11, 2026.

This American Airlines deal was found by Cheapflights users on 1/9. 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.
Mon 2/239:18 amMAF - SJU
1 stop12h 13mAmerican Airlines
Fri 2/277:33 amSJU - MAF
1 stop11h 48mAmerican Airlines
Deal found 1/9$240
This United Airlines deal was found by Cheapflights users on 1/10. 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.
Mon 3/29:43 amMAF - SJU
1 stop9h 43mUnited Airlines
Wed 3/43:46 pmSJU - MAF
1 stop7h 58mUnited Airlines
Deal found 1/10$330
This American Airlines deal was found by Cheapflights users on 1/10. 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.
Mon 3/25:51 pmMAF - SJU
2 stops14h 09mAmerican Airlines
Sat 3/77:00 amSJU - MAF
2 stops15h 11mAmerican Airlines
Deal found 1/10$428
This American Airlines deal was found by Cheapflights users on 1/10. 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.
Thu 1/2910:37 amMAF - SJU
2 stops11h 22mAmerican Airlines
Tue 2/37:07 amSJU - MAF
1 stop17h 47mAmerican Airlines
Deal found 1/10$466
This Southwest deal was found by Cheapflights users on 1/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2911:45 amMAF - SJU
2 stops10h 50mSouthwest
Tue 2/35:40 amSJU - MAF
2 stops10h 30mSouthwest
Deal found 1/10$470
This American Airlines deal was found by Cheapflights users on 1/10. 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.
Fri 2/612:41 pmMAF - SJU
2 stops9h 18mAmerican Airlines
Tue 2/107:07 amSJU - MAF
1 stop15h 42mAmerican Airlines
Deal found 1/10$491
This Southwest deal was found by Cheapflights users on 1/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/62:55 pmMAF - SJU
2 stops7h 45mSouthwest
Tue 2/102:35 pmSJU - MAF
2 stops9h 40mSouthwest
Deal found 1/10$496
This Southwest deal was found by Cheapflights users on 1/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2911:45 amMAF - SJU
2 stops10h 50mSouthwest
Mon 2/22:35 pmSJU - MAF
2 stops9h 40mSouthwest
Deal found 1/10$531
This American Airlines deal was found by Cheapflights users on 1/10. 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.
Thu 1/2910:37 amMAF - SJU
2 stops11h 22mAmerican Airlines
Mon 2/27:07 amSJU - MAF
1 stop13h 11mAmerican Airlines
Deal found 1/10$546
This United Airlines deal was found by Cheapflights users on 1/8. 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.
Tue 1/207:00 amMAF - SDQ
2 stops14h 46mUnited Airlines
Thu 1/222:53 pmSDQ - MAF
2 stops24h 03mUnited Airlines
Deal found 1/8$683
This United Airlines deal was found by Cheapflights users on 1/8. 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.
Mon 4/201:45 pmMAF - SXM
2 stops21h 48mUnited Airlines
Wed 4/221:35 pmSXM - MAF
2 stops22h 37mUnited Airlines
Deal found 1/8$728
This United Airlines deal was found by Cheapflights users on 1/8. 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.
Mon 1/262:55 pmMAF - AUA
2 stops20h 55mUnited Airlines
Thu 1/295:50 pmAUA - MAF
2 stops22h 04mUnited Airlines
Deal found 1/8$797

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 January 11, 2026.
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

Mon 2/23

5:00 am-9:34 pm

2 stops14h 34m

San Juan Luis Munoz Marin Intl

Fri 2/27

7:33 am-10:49 pm

1 stop17h 16m

$240

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 3/2

9:43 am-9:26 pm

1 stop9h 43m

San Juan Luis Munoz Marin Intl

Wed 3/4

3:46 pm-11:15 pm

1 stop9h 29m

$330

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 3/2

5:51 pm-10:00 am

2 stops14h 09m

San Juan Luis Munoz Marin Intl

Sat 3/7

7:33 am-10:49 pm

1 stop17h 16m

$428

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Thu 1/29

10:37 am-11:59 pm

2 stops11h 22m

San Juan Luis Munoz Marin Intl

Tue 2/3

7:07 am-10:54 pm

1 stop17h 47m

$466

MidlandSimpson Bay

MAF - SXM

MAFSXM

Midland Intl

Mon 4/20

1:45 pm-12:33 pm

2 stops21h 48m

Simpson Bay Princess Juliana

Wed 4/22

1:35 pm-11:12 am

2 stops22h 37m

$728

MidlandOranjestad

MAF - AUA

MAFAUA

Midland Intl

Mon 1/26

2:55 pm-1:50 pm

2 stops20h 55m

Oranjestad Reina Beatrix

Thu 1/29

5:50 pm-1:54 pm

2 stops22h 04m

$797

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Fri 2/6

12:41 pm-11:59 pm

2 stops9h 18m

$194

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 6/13

5:23 pm-4:32 am

1 stop10h 09m

$230

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 6/13

5:00 am-9:24 pm

2 stops15h 24m

$355

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 3/7

6:20 pm-9:00 am

2 stops12h 40m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 12 results
1
2

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.

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 January 11, 2026.
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
11,100 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

Food

6.4

Crew

8.0

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
11,100 reviews
American Airlines
7.2
Good
11,100 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Entertainment

6.9

Food

6.4

Crew

8.0

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 9h 43m. 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 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 - Simpson Bay Princess Juliana 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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Alternative routes for Midland to Caribbean Islands

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 January 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$307Average$661FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$353Average$532FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$520Average$590FlexibilityNo cancel feeOn-time63%

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