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Stewart

$88+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SWF
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
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 February 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/78:43 pm
PHL
-
SWF
1 stop14h 25m
Multiple Airlines
Mon 2/911:09 am
SWF
-
PHL
1 stop22h 44m
Multiple Airlines
Deal found 2/3$272
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/187:59 pm
PHL
-
SWF
1 stop15h 33m
Multiple Airlines
Sun 2/2211:48 am
SWF
-
PHL
2 stops28h 49m
Multiple Airlines
Deal found 2/3$340
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 5/305:57 pm
PHL
-
SWF
1 stop15h 41m
Multiple Airlines
Sun 6/710:28 am
SWF
-
PHL
1 stop22h 16m
Multiple Airlines
Deal found 2/3$355
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Wed 2/48:00 am
BWI
-
SWF
1 stop27h 08m
Multiple Airlines
Fri 2/67:33 pm
SWF
-
BWI
1 stop27h 08m
Multiple Airlines
Deal found 2/2$364
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 6/105:58 pm
BWI
-
SWF
1 stop15h 40m
Multiple Airlines
Sun 6/1410:28 am
SWF
-
BWI
1 stop22h 18m
Multiple Airlines
Deal found 2/3$445
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/810:45 pm
PHL
-
SWF
1 stop19h 58m
Multiple Airlines
Sun 2/157:28 pm
SWF
-
PHL
1 stop12h 44m
Multiple Airlines
Deal found 2/3$459
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Wed 2/188:25 pm
BWI
-
SWF
1 stop14h 43m
Multiple Airlines
Sun 2/2211:48 am
SWF
-
BWI
1 stop8h 31m
Multiple Airlines
Deal found 2/2$465
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sat 2/147:07 pm
BWI
-
SWF
1 stop16h 01m
Multiple Airlines
Mon 2/1612:11 pm
SWF
-
BWI
2 stops20h 55m
Multiple Airlines
Deal found 2/1$495
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/59:39 pm
BWI
-
SWF
2 stops13h 52m
Multiple Airlines
Thu 3/1211:48 am
SWF
-
BWI
1 stop9h 10m
Multiple Airlines
Deal found 2/3$555
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 3/158:39 pm
BWI
-
SWF
2 stops14h 52m
Multiple Airlines
Thu 3/1911:48 am
SWF
-
BWI
1 stop9h 10m
Multiple Airlines
Deal found 2/3$612
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/188:25 pm
BWI
-
SWF
1 stop14h 43m
Multiple Airlines
Mon 2/2312:11 pm
SWF
-
BWI
2 stops10h 42m
Multiple Airlines
Deal found 2/3$643
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/269:39 pm
BWI
-
SWF
2 stops13h 52m
Multiple Airlines
Sun 3/111:48 am
SWF
-
BWI
1 stop8h 31m
Multiple Airlines
Deal found 2/3$738

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$340
(Kiwi.com)

One-way from

$88
(Kiwi.com)

Popular in

October

Cheapest in

April

Average price

$186
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. 3% potential increase in price ($6 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 February 2026
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 February 4, 2026.
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

Wed 2/18

7:59 pm-11:32 am

1 stop15h 33m

New Windsor Stewart

Sun 2/22

11:48 am-4:37 pm

2 stops28h 49m

$340

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Sat 5/30

5:57 pm-9:38 am

1 stop15h 41m

New Windsor Stewart

Sun 6/7

10:28 am-8:44 am

1 stop22h 16m

$355

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Wed 6/10

5:58 pm-9:38 am

1 stop15h 40m

New Windsor Stewart

Sun 6/14

10:28 am-8:46 am

1 stop22h 18m

$445

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Wed 2/18

8:25 pm-11:08 am

1 stop14h 43m

New Windsor Stewart

Sun 2/22

11:48 am-8:19 pm

1 stop8h 31m

$465

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Sat 2/14

7:07 pm-11:08 am

1 stop16h 01m

New Windsor Stewart

Mon 2/16

12:11 pm-9:06 am

2 stops20h 55m

$495

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Thu 3/5

9:39 pm-11:31 am

2 stops13h 52m

New Windsor Stewart

Thu 3/12

11:48 am-8:58 pm

1 stop9h 10m

$555

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Sun 3/15

8:39 pm-11:31 am

2 stops14h 52m

New Windsor Stewart

Thu 3/19

11:48 am-8:58 pm

1 stop9h 10m

$612

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Thu 2/26

9:39 pm-11:31 am

2 stops13h 52m

New Windsor Stewart

Sun 3/1

11:48 am-8:19 pm

1 stop8h 31m

$739

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Thu 3/26

8:39 pm-11:31 am

2 stops14h 52m

New Windsor Stewart

Sun 3/29

11:48 am-8:58 pm

1 stop9h 10m

$917

BaltimoreNew Windsor

BWI - SWF

BWISWF

Baltimore/Washington

Tue 3/3

5:58 pm-9:19 am

2 stops39h 21m

$113

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 39 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 $120). 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 Philadelphia - New Windsor Stewart or Washington, D.C. Reagan-National - 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, January is the cheapest month in which you can book a flight from Maryland to New Windsor (average of $120). 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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