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$245+ Cheap flights from Midland (MAF) to Caribbean

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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from Midland to Caribbean

Keep the following information in mind while searching for Midland to Caribbean flight deals. Data was last updated April 17, 2025.

Round-trip from

$409
(United Airlines)

One-way from

$245
(United Airlines)

Popular in

November

Cheapest in

April

Average price

$395
From Midland Intl to Caribbean
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One-way flight from Midland Intl to Caribbean
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Highest demand for flights based on searches. 14% potential increase in price ($101 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

Cheapest flights from Midland to Caribbean
Explore the most affordable flight options available from Midland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

This United Airlines deal was found by Cheapflights users on 4/17. 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 6/97:12 pmMAF - SJU
1 stop9h 18mUnited Airlines
Thu 6/122:05 amSJU - MAF
1 stop7h 46mUnited Airlines
Deal found 4/17$409
This Delta deal was found by Cheapflights users on 4/16. 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.
Sun 5/185:29 amMAF - SJU
2 stops13h 19mDelta
Thu 5/227:30 amSJU - MAF
2 stops17h 32mDelta
Deal found 4/16$505
This American Airlines deal was found by Cheapflights users on 4/17. 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 6/96:17 pmMAF - SJU
1 stop9h 49mAmerican Airlines
Thu 6/1212:59 amSJU - MAF
1 stop15h 46mAmerican Airlines
Deal found 4/17$513
This American Airlines deal was found by Cheapflights users on 4/17. 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 5/176:30 pmMAF - SDQ
2 stops15h 45mAmerican Airlines
Sat 5/2412:15 pmSDQ - MAF
2 stops12h 37mAmerican Airlines
Deal found 4/17$529
This Southwest deal was found by Cheapflights users on 4/17. 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.
Mon 6/912:55 pmMAF - SJU
2 stops9h 10mSouthwest
Fri 6/135:50 pmSJU - MAF
1 stop7h 30mSouthwest
Deal found 4/17$534
This United deal was found by Cheapflights users on 4/17. 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 4/197:00 amMAF - SJU
2 stops25h 14mMultiple Airlines
Sun 4/201:05 amSJU - MAF
2 stops23h 23mMultiple Airlines
Deal found 4/17$1,164
This United Airlines deal was found by Cheapflights users on 4/17. 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 5/175:05 pmMAF - SDQ
2 stops17h 50mUnited Airlines
Sat 5/241:10 pmSDQ - MAF
3 stops33h 44mUnited Airlines
Deal found 4/17$1,237

Cheapflights Fare Finder

Customize your flight search to find flights from Midland to Caribbean 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 17, 2025.
Use the filters below to find and compare flights from Midland to Caribbean that are best for you.

Fly from

Midland

Fly to

Caribbean

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 6/9

7:12 pm-5:30 am

1 stop9h 18m

San Juan Luis Munoz Marin Intl

Thu 6/12

2:05 am-8:51 am

1 stop7h 46m

$409

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sun 5/18

5:29 am-7:48 pm

2 stops13h 19m

San Juan Luis Munoz Marin Intl

Thu 5/22

7:30 am-12:02 am

2 stops17h 32m

$505

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 6/9

6:17 pm-5:06 am

1 stop9h 49m

San Juan Luis Munoz Marin Intl

Thu 6/12

12:59 am-3:45 pm

1 stop15h 46m

$513

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Sat 5/17

6:30 pm-11:15 am

2 stops15h 45m

Santo Domingo Las Americas

Sat 5/24

12:15 pm-11:52 pm

2 stops12h 37m

$529

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 6/9

12:55 pm-11:05 pm

2 stops9h 10m

San Juan Luis Munoz Marin Intl

Fri 6/13

5:50 pm-12:20 am

1 stop7h 30m

$534

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Sat 5/17

5:05 pm-11:55 am

2 stops17h 50m

Santo Domingo Las Americas

Sat 5/24

1:10 pm-9:54 pm

3 stops33h 44m

$1,237

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 4/23

7:00 am-11:57 pm

2 stops15h 57m

$245

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Thu 4/24

6:28 pm-5:00 am

1 stop9h 32m

$288

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Thu 4/24

9:55 am-11:30 pm

2 stops12h 35m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Best time to book a flight from Midland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, September is the cheapest month in which you can book a flight from Midland to Caribbean (average of $254). Flying from Midland to Caribbean 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 CB?

Find hourly flight availability from Midland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 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 as you normally would.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated April 17, 2025.
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,667 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Midland to Caribbean. 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?

    Most people fly from Midland Intl (MAF) if they book a flight from Midland to Caribbean. Midland Intl is conveniently located just 8.2 mi from Midland’s city center.

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

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $245. However, be on the lookout for offers from American Airlines and Southwest, as they are both options that can get you from Midland to Caribbean for a low price.

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

    The most popular flight routes from Midland to Caribbean are Midland Intl - San Juan Luis Munoz Marin Intl, Midland Intl - Montego Bay Sangster Intl and Midland Intl - Santa Clara.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midland to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Midland to Caribbean (average of $254). Flying from Midland to Caribbean 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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Top 3 airlines flying from Midland to Caribbean

Discover the top 3 airlines that operate flights from Midland to Caribbean. 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$358Average$744FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$370Average$661FlexibilityNo cancel feeOn-time69%
DeltaCheapest$384Average$495FlexibilityNo cancel feeOn-timeN/A

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