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Stewart

$94+ Cheap flights from Maryland to New Windsor (SWF)

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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SWF
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Maryland to Stewart

Keep the following information in mind while searching for Maryland to Stewart flight deals. Data was last updated June 12, 2025.

Round-trip from

$228
(Mytrip)

One-way from

$94
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$218
From Maryland to New Windsor Stewart
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One-way flight from Maryland to New Windsor Stewart
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Highest demand for flights based on searches. 17% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Maryland to Stewart

Cheapest flights from Maryland to Stewart
Explore the most affordable flight options available from Maryland to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/306:20 amPHL - SWF
1 stop12h 51mMultiple Airlines
Fri 7/47:56 pmSWF - PHL
1 stop21h 04mMultiple Airlines
Deal found 6/11$228
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/18:38 pmBWI - SWF
1 stop14h 22mMultiple Airlines
Fri 7/47:56 pmSWF - BWI
1 stop27h 01mMultiple Airlines
Deal found 6/10$237
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/249:25 amIAD - SWF
1 stop25h 04mMultiple Airlines
Mon 7/286:11 pmSWF - IAD
3 stops22h 04mMultiple Airlines
Deal found 6/11$309

Cheapflights Fare Finder

Customize your flight search to find flights from Maryland to Stewart 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 June 12, 2025.
Use the filters below to find and compare flights from Maryland to New Windsor that are best for you.

Fly from

Maryland

Fly to

Stewart

Route

Depart

Return

Price

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Mon 6/30

6:20 am-7:11 pm

1 stop12h 51m

New Windsor Stewart

Fri 7/4

7:56 pm-5:00 pm

1 stop21h 04m

$228

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Tue 7/1

8:38 pm-11:00 am

1 stop14h 22m

New Windsor Stewart

Fri 7/4

7:56 pm-10:57 pm

1 stop27h 01m

$237

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Thu 7/24

9:25 am-10:29 am

1 stop25h 04m

New Windsor Stewart

Mon 7/28

6:11 pm-4:15 pm

3 stops22h 04m

$309

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Mon 6/30

6:50 am-7:11 pm

1 stop12h 21m

$95

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Sat 7/19

7:00 am-4:58 pm

2 stops9h 58m

$132

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Sun 7/20

9:25 am-10:29 am

1 stop25h 04m

$134

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Thu 7/10

11:58 am-7:06 pm

2 stops31h 08m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Best time to book a flight from Maryland to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart 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 New Windsor

What is the cheapest month to book a flight from Maryland to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Maryland to New Windsor (average of $109). Flying from Maryland to New Windsor in August is currently the most expensive (average of $219). 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.

Reviews of airlines servicing Stewart

Get insights into the airlines that provide service to Stewart. 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 Stewart. Reviews last updated June 12, 2025.
Allegiant Air
7.3
Good
725 reviews

Boarding

7.6

Food

5.9

Crew

8.1

Comfort

6.8

Overall

7.3

Entertainment

5.5

Reviews

1 / 20
10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.
Allegiant Air
7.3
Good
725 reviews
Allegiant Air
7.3
Good
725 reviews

Boarding

7.6

Food

5.9

Crew

8.1

Comfort

6.8

Overall

7.3

Entertainment

5.5

Reviews

1 / 20
10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

Related info for your journey

Find useful and relevant information for your journey from Maryland to Stewart. 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 into for flights to New Windsor from Maryland?

    Located just 4.3 mi from the city center, New Windsor Stewart (SWF) is the airport most travelers will use when flying to New Windsor from Maryland.

  • What are the most popular routes from Maryland to New Windsor?

    While some choose either Washington, D.C. Dulles Intl - New Windsor Stewart or Philadelphia - New Windsor Stewart, Baltimore/Washington - New Windsor Stewart is the most popular route from Maryland to New Windsor.

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

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

  • How can I find direct flights from Maryland to Stewart?

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

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

    Yes. Cheapflights offers flight deals from Maryland to Stewart 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 New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Maryland to New Windsor (average of $109). Flying from Maryland to New Windsor in August is currently the most expensive (average of $219). 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

Traveling to a place near Maryland?

Book flights to Maryland if you plan to visit one of these locations
Kingston

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