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Stewart

$97+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SWF
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$211
(Kiwi.com)

One-way from

$97
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$189
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. 21% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:21 pmBWI - SWF
1 stop14h 20mMultiple Airlines
Mon 10/2011:01 amSWF - BWI
1 stop12h 31mMultiple Airlines
Deal found 9/14$211
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:33 amPHL - SWF
1 stop29h 08mMultiple Airlines
Mon 10/273:01 pmSWF - PHL
1 stop8h 58mMultiple Airlines
Deal found 9/16$214
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:21 pmBWI - SWF
1 stop14h 20mMultiple Airlines
Mon 10/273:01 pmSWF - BWI
1 stop8h 31mMultiple Airlines
Deal found 9/15$221
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1410:14 amIAD - SWF
1 stop8h 01mAllegiant Air
Sun 11/166:14 pmSWF - IAD
2 stops24h 23mAllegiant Air
Deal found 9/15$303
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/209:39 pmBWI - SWF
1 stop13h 24mMultiple Airlines
Sun 9/217:12 pmSWF - BWI
1 stop12h 17mMultiple Airlines
Deal found 9/13$320
This Mytrip deal was found by Cheapflights users on 9/14. 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.
Fri 10/2410:09 amIAD - SWF
1 stop9h 07mAllegiant Air
Sun 10/267:11 pmSWF - IAD
2 stops25h 24mAllegiant Air
Deal found 9/14$334
This Mytrip deal was found by Cheapflights users on 9/14. 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.
Sun 10/126:19 amPHL - SWF
2 stops10h 36mMultiple Airlines
Sun 10/195:45 pmSWF - PHL
2 stops15h 47mMultiple Airlines
Deal found 9/14$340
This Mytrip deal was found by Cheapflights users on 9/15. 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 10/168:25 amIAD - SWF
3 stops26h 16mMultiple Airlines
Mon 10/2011:01 amSWF - IAD
3 stops24h 22mMultiple Airlines
Deal found 9/15$382
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/18:00 amPHL - SWF
1 stop27h 03mMultiple Airlines
Sun 10/55:45 pmSWF - PHL
2 stops15h 47mMultiple Airlines
Deal found 9/15$391
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/710:14 amIAD - SWF
1 stop8h 01mMultiple Airlines
Sun 11/911:43 amSWF - IAD
1 stop8h 08mMultiple Airlines
Deal found 9/15$428
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1410:14 amIAD - SWF
1 stop8h 01mMultiple Airlines
Sun 11/1611:43 amSWF - IAD
1 stop8h 08mMultiple Airlines
Deal found 9/15$430
This Mytrip deal was found by Cheapflights users on 9/15. 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 10/1310:09 amIAD - SWF
1 stop9h 22mAllegiant Air
Mon 10/2011:01 amSWF - IAD
2 stops9h 45mAllegiant Air
Deal found 9/15$472

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 September 16, 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

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Thu 10/16

8:21 pm-10:41 am

1 stop14h 20m

New Windsor Stewart

Mon 10/20

11:01 am-11:32 pm

1 stop12h 31m

$211

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Thu 10/23

10:54 am-10:41 am

1 stop23h 47m

New Windsor Stewart

Mon 10/27

3:01 pm-11:59 pm

1 stop8h 58m

$213

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Thu 10/23

8:21 pm-10:41 am

1 stop14h 20m

New Windsor Stewart

Mon 10/27

3:01 pm-11:32 pm

1 stop8h 31m

$221

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Fri 11/14

10:14 am-6:15 pm

1 stop8h 01m

New Windsor Stewart

Sun 11/16

6:14 pm-6:37 pm

2 stops24h 23m

$303

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Sun 10/12

6:19 am-4:55 pm

2 stops10h 36m

New Windsor Stewart

Sun 10/19

5:45 pm-9:32 am

2 stops15h 47m

$340

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Thu 10/16

8:25 am-10:41 am

3 stops26h 16m

New Windsor Stewart

Mon 10/20

11:01 am-11:23 am

3 stops24h 22m

$382

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Wed 10/1

8:00 am-11:03 am

1 stop27h 03m

New Windsor Stewart

Sun 10/5

5:45 pm-9:32 am

2 stops15h 47m

$391

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Fri 11/7

10:14 am-6:15 pm

1 stop8h 01m

New Windsor Stewart

Sun 11/9

11:43 am-7:51 pm

1 stop8h 08m

$428

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Fri 11/14

10:14 am-6:15 pm

1 stop8h 01m

New Windsor Stewart

Sun 11/16

11:43 am-7:51 pm

1 stop8h 08m

$430

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Mon 10/13

10:09 am-7:31 pm

1 stop9h 22m

New Windsor Stewart

Mon 10/20

11:01 am-8:46 pm

2 stops9h 45m

$472

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 47 results
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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 December is currently the most expensive (average of $202). 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 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.

  • How long is the flight from Maryland to New Windsor?

    For as low as $303, Allegiant Air can have you in New Windsor from Maryland in 8h 01m. Airlines will cover a distance of 249 mi.

  • 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 December is currently the most expensive (average of $202). 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 New Windsor?

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

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