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Find cheap flights from Midland to Caribbean from $299

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midland to Caribbean departing on 8/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 7/11
Thu 7/18

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Montego Bay
Montego Bay2 stops$472

Good to know

Low season

April

High season

May

Cheapest flight

$299
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 21% lower on average.
Flight from Midland to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Midland to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Midland to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Midland to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean from Midland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Midland to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Caribbean with an airline and back to Midland with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Midland to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Caribbean from Midland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 20% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midland to Caribbean

Need help choosing which airline to fly with from Midland to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10277 reviews
8.6Crew
8.2Boarding
8.0Entertainment
7.4Food
7.9Comfort
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Crew was very cooperative and professional. Passenger's first checked in bag should be free.

My seat was broken. WiFi didn’t work. Gate crew at HOU were rude and condescending. Treated all the passengers badly. Bad experience, United.

Food wasn’t very good, old business seating configuration on an old A340

Not a fan of the diagonal partially enclosed business class seats or how they have to be converted to beds manually by crew. I prefer more isolation and user control for switching to lie flat.

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

There was a group of school age passengers that were very loud and unruly with their chaperones were no where to be found.

On time every leg of the journey and exceptional staff at counter, gate, and on board. I haven’t travelled in US for a long time and was genuinely surprised how pleasant this was.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Trip was smooth bumpy from the wind but no issues at all the crew attendant was very pleasant and had great customer service

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

Nothing, terrible travel experience due to weather and maintenance delays and was left stranded in Austin.

Experience was bad. 3.5 hour delay for a 2.5 hour trip. There was no r Transparency about the reason for the delay and it was done 30 mins at a time.

Everything was great except for the wifi was junk. Crew was super friendly and helpful

The flight was short. However, my bag was delayed and was put on another flight.

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

Flight was cancelled had to move to another gate late again no internet paid for the month and never can use it waste of money

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

Missed the flight because of them and up geting a rental car

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Book cheap flights from Midland to Caribbean

Recent round-trip flight deals

8/24Sat
2 stopsAmerican Airlines
17h 31mMAF-SJU
9/1Sun
2 stopsAmerican Airlines
14h 29mSJU-MAF
$299
8/24Sat
1 stopAmerican Airlines
8h 49mMAF-SJU
9/1Sun
2 stopsAmerican Airlines
11h 09mSJU-MAF
$438
8/23Fri
2 stopsAmerican Airlines
16h 35mMAF-MBJ
8/30Fri
1 stopAmerican Airlines
8h 29mMBJ-MAF
$472
8/23Fri
1 stopAmerican Airlines
25h 40mMAF-MBJ
8/30Fri
1 stopAmerican Airlines
8h 29mMBJ-MAF
$475
8/2Fri
2 stopsDelta
10h 19mMAF-SJU
8/26Mon
2 stopsDelta
12h 48mSJU-MAF
$498
8/16Fri
2 stopsDelta
15h 42mMAF-SJU
8/18Sun
2 stopsDelta
10h 35mSJU-MAF
$514
7/11Thu
1 stopAmerican Airlines
15h 26mMAF-SJU
7/17Wed
2 stopsAmerican Airlines
13h 36mSJU-MAF
$542
8/24Sat
1 stopUnited Airlines
7h 42mMAF-SJU
8/31Sat
2 stopsUnited Airlines
13h 47mSJU-MAF
$548
8/24Sat
2 stopsUnited Airlines
13h 18mMAF-SJU
8/31Sat
2 stopsUnited Airlines
13h 47mSJU-MAF
$598
8/16Fri
1 stopUnited Airlines
9h 19mMAF-SJU
8/18Sun
1 stopUnited Airlines
7h 28mSJU-MAF
$644

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Midland - Caribbean Flights

Departure:

Midland (MAF)United States

Cabin classes: