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Stewart

$87+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SWF
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$173
(Kiwi.com)

One-way from

$87
(Kiwi.com)

Popular in

October

Cheapest in

April

Average price

$237
Provider with most accurate pricing for Washington, D.C. (WAS)-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-New York (NYC) flights.
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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. 7% potential increase in price ($18 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 November 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 November 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/44:38 pmBWI - SWF
1 stop18h 59mMultiple Airlines
Mon 12/87:30 pmSWF - BWI
1 stop13h 52mMultiple Airlines
Deal found 10/31$173
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/59:31 amIAD - SWF
1 stop7h 23mMultiple Airlines
Sun 12/711:43 amSWF - IAD
1 stop8h 41mMultiple Airlines
Deal found 11/2$231
This Mytrip deal was found by Cheapflights users on 10/31. 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 11/169:36 pmBWI - SWF
1 stop13h 35mMultiple Airlines
Thu 11/206:23 pmSWF - BWI
2 stops18h 58mMultiple Airlines
Deal found 10/31$270
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/129:31 amIAD - SWF
1 stop7h 23mMultiple Airlines
Sun 12/1411:43 amSWF - IAD
1 stop8h 41mMultiple Airlines
Deal found 11/1$286
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/99:36 pmBWI - SWF
1 stop13h 35mMultiple Airlines
Thu 11/1311:43 amSWF - BWI
1 stop7h 43mMultiple Airlines
Deal found 11/1$313
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/47:57 pmIAD - SWF
2 stops20h 57mMultiple Airlines
Sun 12/711:43 amSWF - IAD
1 stop8h 41mMultiple Airlines
Deal found 10/31$327
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/2$341
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/15:51 pmBWI - SWF
1 stop18h 12mMultiple Airlines
Fri 12/57:30 pmSWF - BWI
1 stop12h 12mMultiple Airlines
Deal found 10/31$366
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/1$475
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 12/199:10 amIAD - SWF
1 stop7h 28mMultiple Airlines
Sun 12/2111:43 amSWF - IAD
1 stop9h 20mMultiple Airlines
Deal found 11/1$498
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/258:54 pmPHL - SWF
1 stop14h 33mMultiple Airlines
Fri 11/2812:24 pmSWF - PHL
2 stops10h 39mMultiple Airlines
Deal found 11/1$531
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/98:36 pmIAD - SWF
2 stops15h 08mMultiple Airlines
Thu 11/1311:43 amSWF - IAD
1 stop8h 08mMultiple Airlines
Deal found 11/1$567

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 November 3, 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 12/4

4:38 pm-11:37 am

1 stop18h 59m

New Windsor Stewart

Mon 12/8

7:30 pm-9:22 am

1 stop13h 52m

$173

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Fri 12/5

9:31 am-4:54 pm

1 stop7h 23m

New Windsor Stewart

Sun 12/7

11:43 am-8:24 pm

1 stop8h 41m

$231

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Fri 12/12

9:31 am-4:54 pm

1 stop7h 23m

New Windsor Stewart

Sun 12/14

11:43 am-8:24 pm

1 stop8h 41m

$286

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Thu 12/4

7:57 pm-4:54 pm

2 stops20h 57m

New Windsor Stewart

Sun 12/7

11:43 am-8:24 pm

1 stop8h 41m

$327

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

$341

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

$475

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Fri 12/19

9:10 am-4:38 pm

1 stop7h 28m

New Windsor Stewart

Sun 12/21

11:43 am-9:03 pm

1 stop9h 20m

$498

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Tue 11/25

8:54 pm-11:27 am

1 stop14h 33m

New Windsor Stewart

Fri 11/28

12:24 pm-11:03 pm

2 stops10h 39m

$531

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Sun 11/9

8:36 pm-11:44 am

2 stops15h 08m

New Windsor Stewart

Thu 11/13

11:43 am-7:51 pm

1 stop8h 08m

$567

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Sat 11/8

9:08 pm-11:03 am

1 stop13h 55m

New Windsor Stewart

Sun 11/9

1:32 pm-6:42 pm

1 stop5h 10m

$611

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 40 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 $114). Flying from Maryland to New Windsor in December is currently the most expensive (average of $355). 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.

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

    While some choose either Baltimore/Washington - New Windsor Stewart or Philadelphia - New Windsor Stewart, Washington, D.C. Dulles Intl - 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 $114). Flying from Maryland to New Windsor in December is currently the most expensive (average of $355). 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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