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Stewart

$82+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SWF
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

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 12/278:26 pmIAD - SWF
2 stops14h 37mMultiple Airlines
Tue 12/3011:43 amSWF - IAD
1 stop9h 20mMultiple Airlines
Deal found 12/17$715
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.
Wed 12/3110:00 pmPHL - SWF
1 stop13h 03mMultiple Airlines
Sun 1/411:43 amSWF - PHL
1 stop13h 10mMultiple Airlines
Deal found 12/16$730
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.
Mon 12/299:09 pmBWI - SWF
1 stop13h 54mMultiple Airlines
Fri 1/212:24 pmSWF - BWI
2 stops8h 41mMultiple Airlines
Deal found 12/17$736
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.
Fri 12/199:10 amIAD - SWF
1 stop7h 28mMultiple Airlines
Sun 12/2111:43 amSWF - IAD
1 stop9h 20mMultiple Airlines
Deal found 12/15$761
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 12/199:10 amIAD - SWF
1 stop7h 28mMultiple Airlines
Mon 12/2212:24 pmSWF - IAD
2 stops8h 39mMultiple Airlines
Deal found 12/17$792
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 12/1810:00 pmPHL - SWF
2 stops13h 44mMultiple Airlines
Thu 12/2511:43 amSWF - PHL
1 stop8h 56mMultiple Airlines
Deal found 12/17$858
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 12/1910:00 pmBWI - SWF
1 stop10h 55mMultiple Airlines
Sun 12/2111:43 amSWF - BWI
1 stop9h 22mMultiple Airlines
Deal found 12/17$878
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 12/2010:00 pmBWI - SWF
1 stop13h 03mMultiple Airlines
Mon 12/2212:24 pmSWF - BWI
2 stops11h 25mMultiple Airlines
Deal found 12/16$897
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.
Mon 12/229:10 amIAD - SWF
1 stop7h 28mMultiple Airlines
Tue 12/2311:43 amSWF - IAD
1 stop9h 20mMultiple Airlines
Deal found 12/17$908
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 12/2010:15 pmIAD - SWF
1 stop12h 48mMultiple Airlines
Mon 12/2212:24 pmSWF - IAD
2 stops8h 39mMultiple Airlines
Deal found 12/16$910
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.
Mon 12/2210:00 pmPHL - SWF
1 stop13h 03mMultiple Airlines
Mon 12/2912:24 pmSWF - PHL
2 stops12h 16mMultiple Airlines
Deal found 12/17$929
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.
Sun 12/219:58 pmIAD - SWF
2 stops13h 46mMultiple Airlines
Tue 12/2311:43 amSWF - IAD
1 stop9h 20mMultiple Airlines
Deal found 12/16$964

Find flight deals from Maryland to Stewart

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$170
(Mytrip)

One-way from

$82
(Kiwi.com)

Popular in

October

Cheapest in

April

Average price

$187
Provider with most accurate pricing for Washington, D.C. (WAS)-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-New York (NYC) flights.
Search Deals
From Maryland to New Windsor Stewart
Search Deals
One-way flight from Maryland to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 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 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 December 18, 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

Thu 1/8

6:11 pm-10:19 am

1 stop16h 08m

New Windsor Stewart

Mon 1/12

11:09 am-11:50 pm

1 stop12h 41m

$170

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Thu 1/15

5:42 pm-10:19 am

2 stops16h 37m

New Windsor Stewart

Thu 1/22

12:13 pm-8:40 am

1 stop20h 27m

$227

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Thu 2/12

5:45 am-11:31 am

2 stops29h 46m

New Windsor Stewart

Thu 2/19

12:22 pm-11:31 pm

1 stop11h 09m

$321

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Thu 1/1

7:10 am-11:44 am

2 stops28h 34m

New Windsor Stewart

Mon 1/5

11:37 am-9:35 am

1 stop21h 58m

$445

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Wed 1/7

9:09 pm-11:33 am

1 stop14h 24m

New Windsor Stewart

Fri 1/9

12:11 pm-11:47 pm

2 stops11h 36m

$453

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Wed 1/7

9:09 pm-11:33 am

1 stop14h 24m

New Windsor Stewart

Mon 1/12

12:11 pm-11:47 pm

2 stops11h 36m

$486

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Sat 3/7

9:43 pm-8:19 am

1 stop10h 36m

New Windsor Stewart

Thu 3/12

10:09 am-6:58 pm

1 stop8h 49m

$496

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Sun 2/1

10:45 pm-11:31 am

2 stops12h 46m

New Windsor Stewart

Sun 2/8

11:48 am-9:46 pm

1 stop9h 58m

$524

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Sun 1/4

9:09 pm-11:44 am

2 stops14h 35m

New Windsor Stewart

Sun 1/11

12:13 pm-11:47 pm

1 stop11h 34m

$533

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Thu 1/15

8:43 pm-11:31 am

2 stops14h 48m

New Windsor Stewart

Sun 1/18

12:13 pm-10:03 pm

1 stop9h 50m

$558

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 51 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, January is the cheapest month in which you can book a flight from Maryland to New Windsor (average of $133). Flying from Maryland to New Windsor in July is currently the most expensive (average of $282). 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, January is the cheapest month in which you can book a flight from Maryland to New Windsor (average of $133). Flying from Maryland to New Windsor in July is currently the most expensive (average of $282). 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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