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$99+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BWI
Jul 27 — Aug 31
Mon 7/27
Mon 8/3
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 June 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/22. 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 7/3010:28 am
SWF
-
BWI
1 stop25h 42m
Multiple Airlines
Sat 8/11:05 pm
BWI
-
SWF
1 stop20h 33m
Multiple Airlines
Deal found 6/22$206
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 8/1310:28 am
SWF
-
IAD
1 stop9h 10m
Multiple Airlines
Sat 8/155:29 pm
IAD
-
SWF
1 stop16h 09m
Multiple Airlines
Deal found 6/24$208
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 8/1310:28 am
SWF
-
PHL
1 stop14h 15m
Multiple Airlines
Wed 8/264:00 pm
PHL
-
SWF
1 stop26h 41m
Multiple Airlines
Deal found 6/25$212
This Kiwi.com deal was found by Cheapflights users on 6/23. 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 8/1310:28 am
SWF
-
PHL
1 stop14h 20m
Multiple Airlines
Sat 8/154:30 pm
PHL
-
SWF
2 stops17h 08m
Multiple Airlines
Deal found 6/23$240
This Kiwi.com deal was found by Cheapflights users on 6/23. 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 7/910:28 am
SWF
-
IAD
1 stop9h 10m
Multiple Airlines
Sat 7/115:29 pm
IAD
-
SWF
1 stop16h 09m
Multiple Airlines
Deal found 6/23$252
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 8/610:28 am
SWF
-
IAD
1 stop9h 10m
Multiple Airlines
Sun 8/96:30 pm
IAD
-
SWF
1 stop24h 15m
Multiple Airlines
Deal found 6/24$256
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 10/810:18 am
SWF
-
IAD
1 stop10h 03m
Multiple Airlines
Sun 10/117:27 pm
IAD
-
SWF
1 stop16h 02m
Multiple Airlines
Deal found 6/22$259
This Kiwi.com deal was found by Cheapflights users on 6/24. 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.
Sun 7/2610:28 am
SWF
-
BWI
2 stops44h 58m
Multiple Airlines
Sat 8/11:05 pm
BWI
-
SWF
1 stop20h 33m
Multiple Airlines
Deal found 6/24$268
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 8/2511:48 am
SWF
-
BWI
1 stop9h 42m
Multiple Airlines
Sat 8/299:37 pm
BWI
-
SWF
2 stops21h 04m
Multiple Airlines
Deal found 6/26$272
This Kiwi.com deal was found by Cheapflights users on 6/26. 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.
Sun 8/210:28 am
SWF
-
IAD
1 stop9h 10m
Multiple Airlines
Mon 8/312:00 pm
IAD
-
SWF
2 stops23h 08m
Multiple Airlines
Deal found 6/26$290
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 7/116:44 pm
SWF
-
IAD
2 stops44h 56m
Multiple Airlines
Wed 7/226:09 pm
IAD
-
SWF
1 stop15h 29m
Multiple Airlines
Deal found 6/26$297
This Kiwi.com deal was found by Cheapflights users on 6/24. 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.
Sun 9/610:33 am
SWF
-
BWI
1 stop13h 50m
Multiple Airlines
Fri 9/258:00 am
BWI
-
SWF
2 stops27h 39m
Multiple Airlines
Deal found 6/24$301

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 June 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$206
(Kiwi.com)

One-way from

$99
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$272
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. 15% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 June 27, 2026.
Use the filters below to find and compare flights from New Windsor to Maryland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Thu 7/30

10:28 am-12:10 pm

1 stop25h 42m

Baltimore/Washington

Sat 8/1

1:05 pm-9:38 am

1 stop20h 33m

$206

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Thu 8/13

10:28 am-7:38 pm

1 stop9h 10m

Washington, D.C. Dulles Intl

Sat 8/15

5:29 pm-9:38 am

1 stop16h 09m

$208

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Thu 7/9

10:28 am-7:38 pm

1 stop9h 10m

Washington, D.C. Dulles Intl

Sat 7/11

5:29 pm-9:38 am

1 stop16h 09m

$252

New WindsorPhiladelphia

SWF - PHL

SWFPHL

New Windsor Stewart

Thu 8/13

10:28 am-12:48 am

1 stop14h 20m

Philadelphia

Sat 8/15

2:59 pm-9:38 am

1 stop18h 39m

$255

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Thu 8/6

10:28 am-7:38 pm

1 stop9h 10m

Washington, D.C. Dulles Intl

Sun 8/9

6:30 pm-6:45 pm

1 stop24h 15m

$256

New WindsorPhiladelphia

SWF - PHL

SWFPHL

New Windsor Stewart

Thu 8/13

10:28 am-12:43 am

1 stop14h 15m

Philadelphia

Wed 8/26

10:59 pm-6:41 pm

2 stops19h 42m

$257

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Thu 10/8

10:18 am-8:21 pm

1 stop10h 03m

Washington, D.C. Dulles Intl

Sun 10/11

7:27 pm-11:29 am

1 stop16h 02m

$259

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Sun 7/26

10:28 am-7:26 am

2 stops44h 58m

Baltimore/Washington

Sat 8/1

1:05 pm-9:38 am

1 stop20h 33m

$268

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Sat 7/11

6:44 pm-3:40 pm

2 stops44h 56m

Washington, D.C. Dulles Intl

Wed 7/22

6:09 pm-9:38 am

1 stop15h 29m

$297

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Sat 7/18

12:05 pm-12:23 am

2 stops12h 18m

Baltimore/Washington

Wed 7/22

1:05 pm-9:38 am

1 stop20h 33m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/23

Showing 1-10 of 60 resultsSorted by cheapest first
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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
No data available for this route at this time. Please check back soon.

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 - Philadelphia or New Windsor Stewart - Washington, D.C. Dulles Intl 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.

See more FAQs

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Alternative routes for Stewart to Maryland

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