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$238+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Midland to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Midland (MAF) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$355
(United Airlines)

One-way from

$238
(Southwest)
From Midland Intl to Caribbean
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One-way flight from Midland Intl to Caribbean
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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 January 21, 2025.

This American Airlines deal was found by Cheapflights users on 1/21. 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.
Tue 2/1112:24 pmMAF - SJU
2 stops9h 40mAmerican Airlines
Sat 2/156:30 amSJU - MAF
1 stop15h 19mAmerican Airlines
Deal found 1/21$349
This United Airlines deal was found by Cheapflights users on 1/21. 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 2/185:00 amMAF - SJU
1 stop9h 36mUnited Airlines
Tue 2/257:45 amSJU - MAF
2 stops17h 27mUnited Airlines
Deal found 1/21$355
This Southwest deal was found by Cheapflights users on 1/20. 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.
Wed 2/191:55 pmMAF - SJU
2 stops8h 45mSouthwest
Wed 2/266:00 amSJU - MAF
2 stops12h 35mSouthwest
Deal found 1/20$465
This Delta deal was found by Cheapflights users on 1/21. 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.
Wed 3/55:25 amMAF - SJU
2 stops13h 41mDelta
Thu 3/136:15 amSJU - MAF
2 stops18h 51mDelta
Deal found 1/21$485
This deal was found by Cheapflights users on 1/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/52:26 pmMAF - SXM
2 stops22h 39mAmerican Airlines
Sun 2/95:19 pmSXM - MAF
2 stops22h 37mAmerican Airlines
Deal found 1/20$594
This American Airlines deal was found by Cheapflights users on 1/21. 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 5/308:32 pmMAF - MBJ
2 stops16h 18mAmerican Airlines
Tue 6/36:05 pmMBJ - MAF
2 stops15h 37mAmerican Airlines
Deal found 1/21$630
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/176:00 amMAF - SDQ
2 stops13h 31mAmerican Airlines
Mon 2/247:07 amSDQ - MAF
2 stops14h 42mAmerican Airlines
Deal found 1/20$659
This United Airlines deal was found by Cheapflights users on 1/20. 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 3/157:06 pmMAF - MBJ
1 stop17h 54mUnited Airlines
Wed 3/1912:25 pmMBJ - MAF
2 stops20h 35mUnited Airlines
Deal found 1/20$670
This Delta deal was found by Cheapflights users on 1/20. 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.
Fri 1/245:25 amMAF - MBJ
2 stops8h 59mDelta
Sun 1/2612:36 pmMBJ - MAF
2 stops12h 41mDelta
Deal found 1/20$931
This United deal was found by Cheapflights users on 1/20. 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 10/47:02 amMAF - SJU
2 stops9h 08mMultiple Airlines
Mon 10/61:05 amSJU - MAF
2 stops21h 19mMultiple Airlines
Deal found 1/20$969
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/157:06 pmMAF - MBJ
2 stops40h 04mMultiple Airlines
Wed 3/193:05 pmMBJ - MAF
3 stops23h 05mMultiple Airlines
Deal found 1/20$1,130

Find flights from Midland to Caribbean within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 2/11

12:24 pm-12:04 am

2 stops9h 40m

San Juan Luis Munoz Marin Intl

Sat 2/15

6:30 am-7:49 pm

1 stop15h 19m

$349

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 2/18

5:00 am-4:36 pm

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Tue 2/25

7:45 am-11:12 pm

2 stops17h 27m

$355

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 2/19

1:55 pm-12:40 am

2 stops8h 45m

San Juan Luis Munoz Marin Intl

Wed 2/26

6:00 am-4:35 pm

2 stops12h 35m

$465

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 3/5

5:25 am-9:06 pm

2 stops13h 41m

San Juan Luis Munoz Marin Intl

Thu 3/13

6:15 am-12:06 am

2 stops18h 51m

$485

MidlandSimpson Bay

MAF - SXM

MAFSXM

Midland Intl

Wed 2/5

2:26 pm-3:05 pm

2 stops22h 39m

Simpson Bay Princess Juliana

Sun 2/9

5:19 pm-1:56 pm

2 stops22h 37m

$594

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Fri 5/30

8:32 pm-12:50 pm

2 stops16h 18m

Montego Bay Sangster Intl

Tue 6/3

6:05 pm-9:42 am

2 stops15h 37m

$630

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Mon 2/17

6:00 am-9:31 pm

2 stops13h 31m

Santo Domingo Las Americas

Mon 2/24

7:07 am-7:49 pm

2 stops14h 42m

$659

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Sat 3/15

7:06 pm-1:00 pm

1 stop17h 54m

Montego Bay Sangster Intl

Wed 3/19

12:25 pm-9:00 am

2 stops20h 35m

$670

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Sat 3/15

7:06 pm-11:10 am

2 stops40h 04m

Montego Bay Sangster Intl

Wed 3/19

3:05 pm-2:10 pm

3 stops23h 05m

$1,130

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 5/7

6:05 am-5:30 pm

2 stops10h 25m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 12 results
1
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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.

Travel insights for flights from Midland to Caribbean

Get recent, data-driven insights about flights from Midland to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $378). 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 January 21, 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 January 21, 2025.
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Southwest, with whom users have recently found tickets for as low as $238. However, be on the lookout for offers from American Airlines and United Airlines, 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 - Santo Domingo Las Americas.

  • 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 March is currently the most expensive (average of $378). 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.

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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$358Average$770FlexibilityNo cancel feeOn-time71%
DeltaCheapest$384Average$654FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$404Average$728FlexibilityNo cancel feeOn-time69%
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