$165 Find Cheap Flights from Midland to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midland to Caribbean Islands departing on 6/13. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Midland to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Midland to Caribbean Islands, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midland to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Santo Domingo
Santo Domingo2 stops$642
Montego Bay
Montego Bay2 stops$510
Santo Domingo
Santo Domingo2 stops$642
Montego Bay
Montego Bay2 stops$510

Book Cheap Midland to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midland to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midland to Caribbean Islands

Tue, Jan 6 - Tue, Jan 13
United Airlines Logo
9:41 am - 12:36 am
MAF
-
SJU
12h 55m2 stops
United Airlines Logo
7:45 am - 4:21 pm
SJU
-
MAF
10h 36m1 stop
$369United Airlines
Tue, Jan 6 - Tue, Jan 13
United Airlines Logo
9:41 am - 9:26 pm
MAF
-
SJU
9h 45m1 stop
United Airlines Logo
7:45 am - 4:21 pm
SJU
-
MAF
10h 36m1 stop
$415United Airlines
Tue, Jan 6 - Tue, Jan 13
American Airlines Logo
4:55 pm - 1:41 pm
MAF
-
SJU
18h 46m2 stops
American Airlines Logo
6:00 am - 8:49 pm
SJU
-
MAF
16h 49m2 stops
$489American Airlines
Sat, Jan 31 - Sat, Feb 7
American Airlines Logo
12:41 pm - 11:33 am
MAF
-
MBJ
21h 52m2 stops
American Airlines Logo
12:18 pm - 10:54 pm
MBJ
-
MAF
11h 36m2 stops
$510American Airlines
Sat, Jan 31 - Sat, Feb 7
American Airlines Logo
4:55 pm - 3:16 pm
MAF
-
MBJ
21h 21m1 stop
American Airlines Logo
4:14 pm - 10:54 pm
MBJ
-
MAF
7h 40m1 stop
$512American Airlines
Sat, Mar 14 - Wed, Mar 25
American Airlines Logo
6:20 pm - 1:26 pm
MAF
-
MBJ
19h 06m2 stops
American Airlines Logo
10:07 am - 12:06 am
MBJ
-
MAF
13h 59m2 stops
$513American Airlines
Sun, Mar 15 - Wed, Mar 25
American Airlines Logo
8:34 pm - 2:04 pm
MAF
-
MBJ
17h 30m1 stop
American Airlines Logo
3:04 pm - 10:49 pm
MBJ
-
MAF
7h 45m1 stop
$636American Airlines
Sat, Jan 17 - Wed, Jan 21
United Airlines Logo
1:45 pm - 1:41 pm
MAF
-
SDQ
21h 56m2 stops
United Airlines Logo
2:53 pm - 11:18 am
SDQ
-
MAF
22h 25m2 stops
$642United Airlines
Sat, Mar 14 - Wed, Mar 25
American Airlines Logo
8:34 pm - 2:04 pm
MAF
-
MBJ
17h 30m1 stop
American Airlines Logo
3:04 pm - 10:49 pm
MBJ
-
MAF
7h 45m1 stop
$928American Airlines
Booking Insights

KAYAK's insights & trends for Midland to Caribbean Islands flights

Get data-powered insights and trends into flights from Midland to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Midland to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $404, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Midland to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Midland to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Midland to Caribbean Islands is April, when tickets cost $395 (return) on average. On the other hand, the most expensive months are February and July, when the average cost of round-trip tickets is $825 and $780 respectively.

What’s the cheapest day of the week to fly from Midland to Caribbean Islands?

The average price of all round-trip flights from Midland to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

For Midland to Caribbean Islands, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Caribbean Islands back to Midland, the best deals are generally found on Thursday, with Saturday being the most expensive.

Find deals

Good to know

Low seasonOctober
Cheapest flight$165
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Midland to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Midland to Caribbean Islands 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 Islands?

    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 from Midland to Caribbean Islands with an airline and back with another airline.

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

    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 from Midland to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $570 on average. Morning departures are around 40% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $919.

Reviews of the top airline flying from Midland to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Midland to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midland to Caribbean Islands? 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.
7.2
American AirlinesOverall score based on 11054 reviews
8.0Crew
6.5Food
7.5Boarding
7.2Comfort
6.9Entertainment
Airline reviews

Attendants were pleasant and the flight was smooth and relaxed.

10.0 ExcellentDawn C, Dec 2025
DFW - MIA
Read more American Airlines reviews

Attendants were pleasant and the flight was smooth and relaxed.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

I have a gluten allergy so did have any food

We were very rushed by a staff member at the gate when transferring from American Airlines to Fijian. Then the plane stayed put for ages anyhow! The plane was delayed and my bag sent to San Francisco instead of Fiji

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

The only thing to like was that we eventually got to our destination

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Midland (MAF)