HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$262+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midland to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 1, 2025.

Round-trip from

$340
(American Airlines)

One-way from

$262
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$744
From Midland Intl to Caribbean
Search Deals
One-way flight from Midland Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 1, 2025.

This American Airlines deal was found by Cheapflights users on 6/29. 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 9/26:01 amMAF - SJU
2 stops16h 58mAmerican Airlines
Sat 9/67:05 pmSJU - MAF
2 stops16h 42mAmerican Airlines
Deal found 6/29$340
This United Airlines deal was found by Cheapflights users on 7/1. 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 9/112:05 pmMAF - SJU
1 stop7h 33mUnited Airlines
Fri 9/51:05 amSJU - MAF
2 stops13h 57mUnited Airlines
Deal found 7/1$375
This Delta deal was found by Cheapflights users on 6/30. 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.
Mon 8/115:30 amMAF - SJU
2 stops10h 06mDelta
Sat 8/167:30 amSJU - MAF
2 stops10h 38mDelta
Deal found 6/30$545
This Southwest deal was found by Cheapflights users on 7/1. 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 7/232:35 pmMAF - SJU
1 stop6h 50mSouthwest
Tue 7/296:00 amSJU - MAF
2 stops10h 05mSouthwest
Deal found 7/1$580
This Delta deal was found by Cheapflights users on 6/30. 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.
Tue 12/161:10 pmMAF - AUA
2 stops22h 50mDelta
Tue 12/232:15 pmAUA - MAF
2 stops11h 49mDelta
Deal found 6/30$638
This United Airlines deal was found by Cheapflights users on 7/1. 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 7/187:05 pmMAF - MBJ
1 stop18h 25mUnited Airlines
Tue 7/224:12 pmMBJ - MAF
2 stops28h 15mUnited Airlines
Deal found 7/1$777
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Wed 7/91:58 pmMAF - AUA
2 stops23h 02mUnited Airlines
Thu 7/313:10 pmAUA - MAF
2 stops22h 56mUnited Airlines
Deal found 6/29$825

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 July 1, 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

Tue 9/2

6:01 am-11:59 pm

2 stops16h 58m

San Juan Luis Munoz Marin Intl

Sat 9/6

7:05 pm-10:47 am

2 stops16h 42m

$340

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 9/1

12:05 pm-8:38 pm

1 stop7h 33m

San Juan Luis Munoz Marin Intl

Fri 9/5

1:05 am-2:02 pm

2 stops13h 57m

$375

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 8/11

5:30 am-4:36 pm

2 stops10h 06m

San Juan Luis Munoz Marin Intl

Sat 8/16

7:30 am-5:08 pm

2 stops10h 38m

$545

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 7/23

2:35 pm-10:25 pm

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Tue 7/29

6:00 am-3:05 pm

2 stops10h 05m

$580

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Fri 7/18

7:05 pm-1:30 pm

1 stop18h 25m

Montego Bay Sangster Intl

Tue 7/22

4:12 pm-8:27 pm

2 stops28h 15m

$777

MidlandOranjestad

MAF - AUA

MAFAUA

Midland Intl

Wed 7/9

1:58 pm-2:00 pm

2 stops23h 02m

Oranjestad Reina Beatrix

Thu 7/31

3:10 pm-1:06 pm

2 stops22h 56m

$825

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 7/28

8:29 pm-5:06 am

1 stop7h 37m

$262

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 7/28

3:25 pm-12:55 am

2 stops8h 30m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

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 June is currently the most expensive (average of $339). 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 July 1, 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.

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 July 1, 2025.
Read through reviews of airlines operating flights from Midland to Caribbean, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,275 reviews

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,974 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,858 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 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 - Oranjestad Reina Beatrix.

  • 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 June is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to Seattle flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to John F Kennedy Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to Los Angeles flights
Dallas/Fort Worth to Las Vegas flights
George Bush Intcntl to Cancún flights
Dallas/Fort Worth to Cancún flights
Dallas/Fort Worth to Newark flights
Dallas/Fort Worth to Orlando flights
Hobby to Las Vegas flights
Dallas/Fort Worth to Denver flights
Dallas/Fort Worth to Midway flights
Hobby to LaGuardia flights
George Bush Intcntl to Las Vegas flights
Hobby to Seattle flights
Hobby to Newark flights
Hobby to John F Kennedy Intl flights
Dallas/Fort Worth to San Diego flights
Dallas/Fort Worth to Miami flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Hobby to Cancún flights
Dallas/Fort Worth to San Francisco flights
Dallas/Fort Worth to Baltimore flights
Love Field to Seattle flights
Dallas/Fort Worth to Dulles Intl flights
George Bush Intcntl to Newark flights
Hobby to O'Hare Intl flights
Dallas/Fort Worth to Narita flights
Dallas/Fort Worth to Mexico City flights
George Bush Intcntl to Seattle flights
Dallas/Fort Worth to Detroit flights
Dallas/Fort Worth to Fort Lauderdale flights
Dallas/Fort Worth to Cozumel flights
Dallas/Fort Worth to Boston flights
George Bush Intcntl to LaGuardia flights
Hobby to Denver flights
Love Field to Cancún flights
Dallas/Fort Worth to Haneda flights
Hobby to Los Angeles flights
Austin to Las Vegas flights
Dallas/Fort Worth to Heathrow flights
George Bush Intcntl to John F Kennedy Intl flights
Hobby to Philadelphia flights
Dallas/Fort Worth to Portland flights
Dallas/Fort Worth to Minneapolis flights
Dallas/Fort Worth to Burbank flights
George Bush Intcntl to O'Hare Intl flights
Austin to Denver flights
Hobby to Orlando flights

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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$358Average$773FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$370Average$664FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$513Average$544FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.