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Caribbean Islands

$290+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Round-trip from

$440
(American Airlines)

One-way from

$290
(United Airlines)

Popular in

November

Cheapest in

January

Average price

$445
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. 13% potential increase in price ($98 potential increase over avg. RT price).
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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 April 2025
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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 April 29, 2025.

This American Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 5/178:26 pmMAF - SJU
1 stop7h 46mAmerican Airlines
Wed 5/2111:50 amSJU - MAF
2 stops11h 34mAmerican Airlines
Deal found 4/27$440
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/125:30 amMAF - SJU
2 stops16h 18mDelta
Mon 6/166:15 amSJU - MAF
2 stops11h 19mDelta
Deal found 4/27$505
This Southwest deal was found by Cheapflights users on 4/27. 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.
Sat 7/1210:20 amMAF - SJU
1 stop10h 40mSouthwest
Wed 7/167:00 amSJU - MAF
1 stop9h 05mSouthwest
Deal found 4/27$550
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 5/179:00 amMAF - SJU
2 stops13h 54mUnited Airlines
Tue 5/201:05 amSJU - MAF
2 stops14h 08mUnited Airlines
Deal found 4/27$560
This American Airlines deal was found by Cheapflights users on 4/28. 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 6/128:28 pmMAF - SDQ
2 stops17h 52mAmerican Airlines
Thu 6/197:00 amSDQ - MAF
2 stops16h 57mAmerican Airlines
Deal found 4/28$619
This American Airlines deal was found by Cheapflights users on 4/27. 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 5/166:30 pmMAF - MBJ
2 stops19h 06mAmerican Airlines
Sun 5/183:40 pmMBJ - MAF
2 stops17h 08mAmerican Airlines
Deal found 4/27$765
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Fri 5/165:00 amMAF - MBJ
1 stop8h 30mUnited Airlines
Sun 5/182:40 pmMBJ - MAF
1 stop9h 06mUnited Airlines
Deal found 4/27$1,242
This United deal was found by Cheapflights users on 4/27. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/177:00 amMAF - SJU
2 stops10h 20mMultiple Airlines
Wed 5/214:55 pmSJU - MAF
3 stops29h 59mMultiple Airlines
Deal found 4/27$1,247

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 April 29, 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

Sat 5/17

8:26 pm-5:12 am

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Wed 5/21

6:30 am-10:24 pm

1 stop16h 54m

$440

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Thu 6/12

5:30 am-10:48 pm

2 stops16h 18m

San Juan Luis Munoz Marin Intl

Mon 6/16

6:15 am-4:34 pm

2 stops11h 19m

$505

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 7/12

10:20 am-10:00 pm

1 stop10h 40m

San Juan Luis Munoz Marin Intl

Wed 7/16

7:00 am-3:05 pm

1 stop9h 05m

$550

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 5/17

7:00 am-3:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Tue 5/20

1:05 am-2:13 pm

2 stops14h 08m

$560

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Thu 6/12

8:28 pm-3:20 pm

2 stops17h 52m

Santo Domingo Las Americas

Thu 6/19

7:00 am-10:57 pm

2 stops16h 57m

$619

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Fri 5/16

6:30 pm-1:36 pm

2 stops19h 06m

Montego Bay Sangster Intl

Sun 5/18

3:40 pm-8:48 am

2 stops17h 08m

$765

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Fri 5/16

5:00 am-1:30 pm

1 stop8h 30m

Montego Bay Sangster Intl

Sun 5/18

2:40 pm-11:46 pm

1 stop9h 06m

$1,242

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 5/17

7:00 am-6:20 pm

2 stops10h 20m

San Juan Luis Munoz Marin Intl

Wed 5/21

4:55 pm-9:54 pm

3 stops29h 59m

$1,247

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 5/7

7:00 am-11:57 pm

2 stops15h 57m

$290

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Thu 5/8

9:18 am-8:09 pm

2 stops9h 51m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 11 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, September is the cheapest month in which you can book a flight from Midland to Caribbean Islands (average of $254). Flying from Midland to Caribbean Islands in December is currently the most expensive (average of $336). 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 April 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Midland to Caribbean Islands as you normally would.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 29, 2025.
Read through reviews of airlines operating flights from Midland to Caribbean Islands, such as Southwest, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,292 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,292 reviews
Southwest
8.0
Very good
4,292 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,292 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,292 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,292 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

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

    $290 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 $295 and $308, 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 - Oranjestad Reina Beatrix, Midland Intl - San Juan Luis Munoz Marin Intl or Midland Intl - Montego Bay Sangster Intl 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, September is the cheapest month in which you can book a flight from Midland to Caribbean Islands (average of $254). Flying from Midland to Caribbean Islands in December is currently the most expensive (average of $336). 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 2 airlines flying from Midland to Caribbean Islands

Discover the top 2 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$358Average$738FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$370Average$664FlexibilityNo cancel feeOn-time69%

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