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$87+ Cheap flights from New Windsor (SWF) to Maryland

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

Cheapest flights from Stewart to Maryland
Explore the most affordable flight options available from Stewart to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Mon 12/228:25 pmSWF - BWI
1 stop17h 04mMultiple Airlines
Mon 12/299:09 pmBWI - SWF
1 stop13h 54mMultiple Airlines
Deal found 12/16$507
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Mon 12/228:25 pmSWF - BWI
1 stop17h 04mMultiple Airlines
Sun 12/2810:00 pmBWI - SWF
1 stop14h 02mMultiple Airlines
Deal found 12/15$531
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/2511:43 amSWF - BWI
1 stop9h 22mMultiple Airlines
Mon 12/299:09 pmBWI - SWF
1 stop13h 54mMultiple Airlines
Deal found 12/16$540
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/207:50 pmSWF - IAD
2 stops41h 52mMultiple Airlines
Mon 12/299:58 pmIAD - SWF
1 stop13h 05mMultiple Airlines
Deal found 12/17$554
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Mon 12/2212:24 pmSWF - IAD
2 stops8h 39mMultiple Airlines
Mon 12/299:58 pmIAD - SWF
1 stop13h 05mMultiple Airlines
Deal found 12/16$587
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Sat 12/209:45 amSWF - BWI
1 stop14h 04mMultiple Airlines
Mon 12/228:18 pmBWI - SWF
2 stops14h 45mMultiple Airlines
Deal found 12/16$610
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Fri 12/198:11 pmSWF - IAD
1 stop25h 19mMultiple Airlines
Sat 12/278:26 pmIAD - SWF
2 stops14h 37mMultiple Airlines
Deal found 12/16$629
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Mon 12/228:25 pmSWF - BWI
1 stop17h 04mMultiple Airlines
Sat 12/2710:00 pmBWI - SWF
1 stop13h 03mMultiple Airlines
Deal found 12/16$629
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/198:11 pmSWF - IAD
1 stop25h 19mMultiple Airlines
Sun 12/289:58 pmIAD - SWF
1 stop14h 04mMultiple Airlines
Deal found 12/17$655
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/1811:43 amSWF - PHL
1 stop8h 56mMultiple Airlines
Thu 12/258:54 pmPHL - SWF
1 stop14h 13mMultiple Airlines
Deal found 12/17$693
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Mon 12/2212:24 pmSWF - IAD
2 stops8h 39mMultiple Airlines
Sat 12/2710:15 pmIAD - SWF
1 stop12h 48mMultiple Airlines
Deal found 12/16$702
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/2311:43 amSWF - IAD
1 stop9h 20mMultiple Airlines
Wed 12/247:01 pmIAD - SWF
2 stops40h 06mMultiple Airlines
Deal found 12/17$714

Find flight deals from Stewart to Maryland

Keep the following information in mind while searching for Stewart to Maryland flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$318
(Kiwi.com)

One-way from

$87
(Mytrip)

Popular in

January

Cheapest in

April

Average price

$256
Provider with most accurate pricing for New York (NYC)-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Washington, D.C. (WAS) flights.
Search Deals
From New Windsor Stewart to Maryland
Search Deals
One-way flight from New Windsor Stewart to Maryland
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Maryland 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 December 18, 2025.
Use the filters below to find and compare flights from New Windsor to Maryland that are best for you.

Fly from

Stewart

Fly to

Maryland

Route

Depart

Return

Price

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Mon 12/22

8:25 pm-1:29 pm

1 stop17h 04m

Baltimore/Washington

Mon 12/29

9:09 pm-11:03 am

1 stop13h 54m

$507

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Mon 12/22

8:25 pm-1:29 pm

1 stop17h 04m

Baltimore/Washington

Sun 12/28

10:00 pm-12:02 pm

1 stop14h 02m

$531

New WindsorPhiladelphia

SWF - PHL

SWFPHL

New Windsor Stewart

Sun 2/1

12:13 pm-9:44 pm

1 stop9h 31m

Philadelphia

Wed 2/4

8:25 pm-11:08 am

1 stop14h 43m

$539

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Thu 12/25

11:43 am-9:05 pm

1 stop9h 22m

Baltimore/Washington

Mon 12/29

9:09 pm-11:03 am

1 stop13h 54m

$540

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Sat 12/20

9:45 am-11:49 pm

1 stop14h 04m

Baltimore/Washington

Mon 12/22

8:18 pm-11:03 am

2 stops14h 45m

$610

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Mon 12/22

8:25 pm-1:29 pm

1 stop17h 04m

Baltimore/Washington

Sat 12/27

10:00 pm-11:03 am

1 stop13h 03m

$629

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Thu 4/2

11:48 am-9:13 pm

1 stop9h 25m

Washington, D.C. Dulles Intl

Sun 4/5

9:58 pm-11:31 am

2 stops13h 33m

$715

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Thu 12/25

11:43 am-9:05 pm

1 stop9h 22m

Baltimore/Washington

Sun 12/28

10:00 pm-11:44 am

2 stops13h 44m

$751

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Sun 12/21

11:43 am-9:05 pm

1 stop9h 22m

Baltimore/Washington

Mon 12/29

9:09 pm-11:03 am

1 stop13h 54m

$768

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Tue 12/23

11:43 am-7:22 am

1 stop19h 39m

Baltimore/Washington

Wed 12/24

7:44 pm-11:07 am

2 stops39h 23m

$768

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 38 results
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Best time to book a flight from Stewart to Maryland

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

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

Currently, September is the cheapest month in which you can book a flight from New Windsor to Maryland (average of $121). Flying from New Windsor to Maryland in February is currently the most expensive (average of $706). 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 Stewart to Maryland. 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 from for flights from New Windsor to Maryland?

    New Windsor Stewart (SWF), located 4.3 mi from the city center, is the airport you fly out of when you book flights from New Windsor to Maryland.

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

    Most travelers choose New Windsor Stewart - Baltimore/Washington, New Windsor Stewart - Washington, D.C. Dulles Intl or New Windsor Stewart - Philadelphia when deciding on the best route from New Windsor to Maryland.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from New Windsor to Maryland (average of $121). Flying from New Windsor to Maryland in February is currently the most expensive (average of $706). 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

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