How many flights depart from Maryland to Caribbean Islands on average per week?

207 flights are operational weekly from Maryland to Caribbean Islands as of April 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.

What airlines fly to Caribbean Islands?

Spirit Airlines, Southwest and Frontier are the top three most popular airlines that fly to Caribbean Islands from Maryland according to our data. Spirit Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 8 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

How many flights depart from Maryland to Caribbean Islands on average per day?

The number of flights available between Maryland and Caribbean Islands is 29 per day as of April 2026. The most frequent departure time is 6:00AM, with 75% of daily flights leaving at noon.

What is the cheapest airline that flies from Maryland to Caribbean Islands?

Frontier, Southwest, and Delta are the most popular carriers operating from Maryland to Caribbean Islands

When did momondo last update prices for flights from Maryland to Caribbean Islands?

Prices for flights from Maryland to Caribbean Islands are updated daily.

How many operators does momondo search for flights from Maryland to Caribbean Islands?

The number of operators available for flights from Maryland to Caribbean Islands is 11 as of April 2026.

How old do you have to be to fly from Maryland to Caribbean Islands?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maryland to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$80 Cheap Flights from Maryland to Caribbean Islands in 2026

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Find the cheapest flights from Maryland to Caribbean Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:17 pm - 6:07 pm

PHL

SJU

3h 50mnonstop

7:20 am - 2:49 pm

SJU

PHL

7h 29m

1 stop

$165Frontier

Mon, May 4 - Mon, May 11

7:00 am - 10:44 am

PHL

SJU

3h 44mnonstop

7:30 am - 2:49 pm

SJU

PHL

7h 19m

1 stop

$167Multiple Airlines

Mon, May 11 - Wed, May 13

9:02 pm - 12:54 am

PHL

SJU

3h 52mnonstop

6:46 pm - 10:54 pm

SJU

PHL

4h 08mnonstop

$168Multiple Airlines

Wed, Apr 29 - Thu, May 14

9:02 pm - 12:54 am

PHL

SJU

3h 52mnonstop

2:09 am - 6:12 am

SJU

PHL

4h 03mnonstop

$172Spirit Airlines

Sat, Apr 25 - Sun, Apr 26

10:54 am - 11:24 pm

PHL

SJU

12h 30m

1 stop

2:09 am - 6:12 am

SJU

PHL

4h 03mnonstop

$173Spirit Airlines

Thu, Apr 23 - Sat, Apr 25

8:15 am - 12:20 pm

IAD

STT

4h 05mnonstop

4:45 pm - 8:58 pm

STT

IAD

4h 13mnonstop

$261United Airlines

Tue, May 5 - Tue, May 12

8:15 am - 12:20 pm

IAD

STT

4h 05mnonstop

1:22 pm - 11:59 pm

STT

IAD

10h 37m

1 stop

$266United Airlines

Tue, May 5 - Tue, May 12

8:11 pm - 12:07 pm

IAD

STT

15h 56m

1 stop

2:30 pm - 11:59 pm

STT

IAD

9h 29m

1 stop

$270American Airlines

Mon, May 4 - Wed, May 13

8:11 pm - 10:47 am

IAD

STT

14h 36m

1 stop

1:15 pm - 7:25 pm

STT

IAD

6h 10m

1 stop

$275American Airlines

Wed, May 6 - Wed, May 13

7:06 am - 2:48 pm

IAD

STT

7h 42m

1 stop

3:05 pm - 12:42 am

STT

IAD

9h 37m

1 stop

$291Delta

Tue, Apr 21 - Thu, Apr 30

Frontier flights from Maryland to Caribbean Islands

Our best Frontier deals on Maryland to Caribbean Islands flight tickets

Frontier

May 4

PHL2:17 pmPhiladelphia

3h 50m

SJU6:07 pmSan Juan Luis Munoz Marin Intl

May 11

SJU7:20 amSan Juan Luis Munoz Marin Intl

7h 29m

1 stop

PHL2:49 pmPhiladelphia

$165

Frontier

Apr 22

PHL6:25 pmPhiladelphia

29h 34m

1 stop

SJU11:59 pmSan Juan Luis Munoz Marin Intl

Apr 28

SJU3:08 amSan Juan Luis Munoz Marin Intl

13h 26m

1 stop

PHL4:34 pmPhiladelphia

$168

Frontier

Apr 21

PHL11:40 amPhiladelphia

3h 50m

SJU3:30 pmSan Juan Luis Munoz Marin Intl

Apr 21

SJU1:59 amSan Juan Luis Munoz Marin Intl

4h 09m

PHL6:08 amPhiladelphia

$169

JetBlue flights from Maryland to Caribbean Islands

Our best JetBlue deals on Maryland to Caribbean Islands flight tickets

JetBlue

Apr 22

DCA8:00 amWashington, D.C. Reagan-National

3h 43m

SJU11:43 amSan Juan Luis Munoz Marin Intl

Apr 27

SJU6:00 pmSan Juan Luis Munoz Marin Intl

3h 56m

DCA9:56 pmWashington, D.C. Reagan-National

$328

JetBlue

May 4

DCA8:00 amWashington, D.C. Reagan-National

3h 45m

SJU11:45 amSan Juan Luis Munoz Marin Intl

May 5

SJU6:00 pmSan Juan Luis Munoz Marin Intl

3h 55m

DCA9:55 pmWashington, D.C. Reagan-National

$333

JetBlue

May 4

DCA8:00 amWashington, D.C. Reagan-National

3h 45m

SJU11:45 amSan Juan Luis Munoz Marin Intl

May 4

SJU10:55 pmSan Juan Luis Munoz Marin Intl

9h 04m

1 stop

DCA7:59 amWashington, D.C. Reagan-National

$336

momondo Fare Finder

Use the filters below to find and compare flights from Maryland to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 5/4

2:17 pm-6:07 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Mon 5/11

7:20 am-2:49 pm

1 stop7h 29m

$165

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 5/11

7:00 am-10:44 am

Nonstop3h 44m

San Juan Luis Munoz Marin Intl

Wed 5/13

7:30 am-2:49 pm

1 stop7h 19m

$167

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Wed 4/29

9:02 pm-12:54 am

Nonstop3h 52m

San Juan Luis Munoz Marin Intl

Thu 5/14

6:46 pm-10:54 pm

Nonstop4h 08m

$168

Quickest round-trip

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sat 4/25

9:02 pm-12:54 am

Nonstop3h 52m

San Juan Luis Munoz Marin Intl

Sun 4/26

2:09 am-6:12 am

Nonstop4h 03m

$172

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Thu 4/23

10:54 am-11:24 pm

1 stop12h 30m

San Juan Luis Munoz Marin Intl

Sat 4/25

2:09 am-6:12 am

Nonstop4h 03m

$173

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Tue 5/5

8:15 am-12:20 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 5/12

4:45 pm-8:58 pm

Nonstop4h 13m

$261

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Tue 5/5

8:15 am-12:20 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 5/12

1:22 pm-11:59 pm

1 stop10h 37m

$266

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Mon 5/4

8:11 pm-12:07 pm

1 stop15h 56m

Saint Thomas Island Cyril E King

Wed 5/13

2:30 pm-11:59 pm

1 stop9h 29m

$270

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Wed 5/6

8:11 pm-10:47 am

1 stop14h 36m

Saint Thomas Island Cyril E King

Wed 5/13

1:15 pm-7:25 pm

1 stop6h 10m

$275

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Tue 4/21

7:06 am-2:48 pm

1 stop7h 42m

Saint Thomas Island Cyril E King

Thu 4/30

3:05 pm-12:42 am

1 stop9h 37m

$291

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Maryland to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean Islands?

The month of July is, on average, the cheapest month to fly to Caribbean Islands from Maryland, with most prices found around $298. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Maryland averaging around $299.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Maryland to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $293. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $355. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Maryland to Caribbean Islands in the afternoon for as low as $277. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the evening because they tend to be around $405. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Maryland to Caribbean Islands flight route?

Fly from Baltimore/Washington to San Juan Luis Munoz Marin Intl for the best Maryland - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Maryland when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $387 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Maryland for as low as $339 on momondo.

What cabin class options are available on Maryland to Caribbean Islands flights?

There are 4 cabin classes available to choose from on Maryland to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Maryland to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Maryland to Caribbean Islands.

Cheap Maryland to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maryland to Caribbean Islands

Fastest flight time	2h 30m
Direct flights	Every day
Airports in Caribbean Islands	99 airports

The fastest flight from Maryland to Caribbean Islands takes 2h 30m

Direct flights go from Maryland to Caribbean Islands every day.

There are 99 airports in Caribbean Islands. From Maryland there are direct flights to Montego Bay Sangster Intl (MBJ), San Juan Luis Munoz Marin Intl (SJU).

Search flight deals

Frequently asked questions about flying from Maryland to Caribbean Islands

When did momondo last update prices for flights from Maryland to Caribbean Islands?
Prices for flights from Maryland to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Maryland to Caribbean Islands?
The number of operators available for flights from Maryland to Caribbean Islands is 11 as of April 2026.
How old do you have to be to fly from Maryland to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maryland to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Maryland to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Maryland to Caribbean Islands is Boeing 737 MAX 8, representing 17.66% of all bookings. The subsequent popular models are Airbus A320-100/200 at 10.55%, Boeing 737-800 Passenger/BBJ2 (winglets) at 10.02%, and Airbus A320neo at 8.40%.

Best airlines flying from Maryland to Caribbean Islands

Compare and see reviews for airlines that fly from Maryland to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $124	Free Cancellation	Rating 6.3 8,607 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $143	Free Cancellation	Rating 5.7 2,997 reviews	Search Frontier flights
JetBlue	PriceFrom $146	Free Cancellation	Rating 7.2 2,928 reviews	Search JetBlue flights
United Airlines	PriceFrom $172	Free Cancellation	Rating 7.4 9,562 reviews	Search United Airlines flights
Delta	PriceFrom $172	Free Cancellation	Rating 7.9 8,402 reviews	Search Delta flights
American Airlines	PriceFrom $225	Free Cancellation	Rating 7.1 11,564 reviews	Search American Airlines flights
Southwest	PriceFrom $346	Free Cancellation	Rating 8.0 4,335 reviews	Search Southwest flights
Copa Airlines	PriceFrom $360	Free Cancellation	Rating 7.5 1,575 reviews	Search Copa Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Maryland to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Maryland to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Maryland to Caribbean Islands with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean Islands from Maryland with this policy.

How can momondo help me find flights from Maryland to Caribbean Islands?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Maryland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Maryland to Caribbean Islands right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Maryland to Caribbean Islands flights. All you need is a valid email address and we will do the rest; it is that quick and easy.