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Cayman Islands

$104+ Cheap flights from Maryland to the Cayman Islands

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — GCM
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheap flight deals from Maryland to Cayman Islands

Keep the following information in mind while searching for Maryland to Cayman Islands flight deals. Data was last updated September 14, 2025.

Round-trip from

$311
(Expedia)

One-way from

$104
(Priceline)

Popular in

November

Cheapest in

May

Average price

$645

Good round-trip deal

$547 or less
From Maryland to Cayman Islands
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One-way flight from Maryland to Cayman Islands
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Highest demand for flights based on searches. 9% potential increase in price ($61 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Maryland to Cayman Islands.
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Find flight deals from Maryland to Cayman Islands

Cheapest flights from Maryland to Cayman Islands
Explore the most affordable flight options available from Maryland to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2025.

This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:15 amPHL - GCM
1 stop5h 45mSpirit Airlines
Sat 12/1311:55 amGCM - PHL
1 stop12h 37mSpirit Airlines
Deal found 9/13$311
This Priceline deal was found by Cheapflights users on 9/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:10 amBWI - GCM
1 stop5h 50mSpirit Airlines
Sun 12/711:55 amGCM - BWI
1 stop11h 59mSpirit Airlines
Deal found 9/13$326
This Priceline deal was found by Cheapflights users on 9/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/299:20 amPHL - GCM
1 stop27h 05mMultiple Airlines
Sat 12/1311:55 amGCM - PHL
1 stop12h 37mMultiple Airlines
Deal found 9/13$374
This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/73:30 pmPHL - GCM
2 stops44h 55mMultiple Airlines
Sat 12/1311:55 amGCM - PHL
1 stop12h 37mMultiple Airlines
Deal found 9/13$383
This Air Canada deal was found by Cheapflights users on 9/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:00 amDCA - GCM
2 stops30h 25mAir Canada
Thu 11/61:30 pmGCM - DCA
2 stops22h 49mAir Canada
Deal found 9/12$413
This Air Canada deal was found by Cheapflights users on 9/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/299:00 amIAD - GCM
1 stop27h 25mAir Canada
Thu 11/61:30 pmGCM - IAD
1 stop26h 21mAir Canada
Deal found 9/12$413
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:15 amDCA - GCM
1 stop8h 16mJetBlue
Sat 11/12:44 pmGCM - DCA
1 stop7h 14mJetBlue
Deal found 9/12$414
This Trip.com deal was found by Cheapflights users on 9/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:24 amDCA - GCM
1 stop8h 07mJetBlue
Mon 11/33:45 pmGCM - DCA
1 stop7h 13mJetBlue
Deal found 9/12$417
This Air Canada deal was found by Cheapflights users on 9/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/204:35 pmPHL - GCM
1 stop19h 50mAir Canada
Thu 11/271:30 pmGCM - PHL
2 stops25h 17mAir Canada
Deal found 9/12$420
This Air Canada deal was found by Cheapflights users on 9/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:50 pmDCA - GCM
1 stop18h 35mAir Canada
Thu 11/61:30 pmGCM - DCA
2 stops22h 49mAir Canada
Deal found 9/12$423
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2612:55 pmDCA - GCM
2 stops23h 30mAir Canada
Tue 12/21:30 pmGCM - DCA
1 stop9h 05mAir Canada
Deal found 9/13$430
This Air Canada deal was found by Cheapflights users on 9/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/264:25 pmIAD - GCM
1 stop20h 00mAir Canada
Tue 12/21:30 pmGCM - IAD
2 stops26h 51mAir Canada
Deal found 9/13$430

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maryland to Cayman Islands 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 September 14, 2025.
Use the filters below to find and compare flights from Maryland to the Cayman Islands that are best for you.

Fly from

Maryland

Fly to

Cayman Islands

Route

Depart

Return

Price

PhiladelphiaGeorge Town

PHL - GCM

PHLGCM

Philadelphia

Sat 2/28

6:00 am-5:07 pm

1 stop11h 07m

George Town Owen Roberts Intl

Sat 3/7

3:55 pm-12:13 am

1 stop8h 18m

$406

BaltimoreGeorge Town

BWI - GCM

BWIGCM

Baltimore/Washington

Tue 1/20

7:35 am-12:55 pm

1 stop5h 20m

George Town Owen Roberts Intl

Thu 1/29

1:50 pm-8:50 pm

1 stop7h 00m

$407

Washington, D.C.George Town

DCA - GCM

DCAGCM

Washington, D.C. Reagan-National

Thu 1/22

7:10 am-2:55 pm

1 stop7h 45m

George Town Owen Roberts Intl

Mon 1/26

2:40 pm-10:57 pm

1 stop8h 17m

$410

Washington, D.C.George Town

DCA - GCM

DCAGCM

Washington, D.C. Reagan-National

Tue 2/17

7:00 am-2:55 pm

1 stop7h 55m

George Town Owen Roberts Intl

Tue 3/17

2:10 pm-10:57 pm

1 stop7h 47m

$414

Washington, D.C.George Town

DCA - GCM

DCAGCM

Washington, D.C. Reagan-National

Sun 10/26

6:15 am-1:31 pm

1 stop8h 16m

George Town Owen Roberts Intl

Sat 11/1

2:44 pm-10:58 pm

1 stop7h 14m

$414

Washington, D.C.George Town

DCA - GCM

DCAGCM

Washington, D.C. Reagan-National

Mon 10/27

6:24 am-1:31 pm

1 stop8h 07m

George Town Owen Roberts Intl

Mon 11/3

3:45 pm-10:58 pm

1 stop7h 13m

$417

PhiladelphiaGeorge Town

PHL - GCM

PHLGCM

Philadelphia

Thu 11/20

4:35 pm-12:25 pm

1 stop19h 50m

George Town Owen Roberts Intl

Thu 11/27

1:30 pm-2:47 pm

2 stops25h 17m

$420

PhiladelphiaGeorge Town

PHL - GCM

PHLGCM

Philadelphia

Mon 12/8

3:30 pm-12:25 pm

2 stops20h 55m

George Town Owen Roberts Intl

Fri 12/12

1:30 pm-3:49 pm

1 stop26h 19m

$420

Washington, D.C.George Town

DCA - GCM

DCAGCM

Washington, D.C. Reagan-National

Thu 12/4

6:59 am-12:25 pm

1 stop29h 26m

George Town Owen Roberts Intl

Tue 12/9

1:30 pm-6:05 pm

1 stop28h 35m

$430

Washington, D.C.George Town

DCA - GCM

DCAGCM

Washington, D.C. Reagan-National

Wed 11/26

12:55 pm-12:25 pm

2 stops23h 30m

George Town Owen Roberts Intl

Tue 12/2

1:30 pm-3:31 pm

2 stops26h 01m

$430

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 60 results
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Best time to book a flight from Maryland to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Maryland 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 Maryland to the Cayman Islands

What is the cheapest month to book a flight from Maryland to Cayman Islands?

Currently, January is the cheapest month in which you can book a flight from Maryland to Cayman Islands (average of $467). Flying from Maryland to Cayman Islands in March is currently the most expensive (average of $594). 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.

Related info for your journey

Find useful and relevant information for your journey from Maryland to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Maryland to Cayman Islands?

    There are many flights that can get you from Maryland to Cayman Islands in 5h 20m. Fly via JetBlue, Southwest, or United Airlines to get the fastest option. The distance from Maryland to Cayman Islands is about 1401 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Maryland to Cayman Islands one-way?

    $137 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Southwest and United Airlines, with prices starting from $151 and $171, respectively.

  • Can I find deals for flights from Maryland to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Maryland to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Maryland to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Maryland to Cayman Islands.

  • Can I find deals for business class flights from Maryland to Cayman Islands?

    Yes. Cheapflights offers flight deals from Maryland to Cayman Islands 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 Maryland to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Maryland to Cayman Islands (average of $467). Flying from Maryland to Cayman Islands in March is currently the most expensive (average of $594). 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

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Alternative routes for Maryland to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Maryland to Cayman Islands

Discover the top 3 airlines that operate flights from Maryland to Cayman Islands. 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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$456Average$560FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$464Average$571FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$517Average$698FlexibilityNo cancel feeOn-time63%

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