HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Maryland

$105+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BWI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Maryland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Stewart to Maryland

Keep the following information in mind while searching for Stewart to Maryland flight deals. Data was last updated September 16, 2025.

Round-trip from

$212
(Kiwi.com)

One-way from

$105
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$232
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. 19% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find 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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/312:11 pmSWF - BWI
1 stop11h 14mMultiple Airlines
Sun 10/58:21 pmBWI - SWF
1 stop13h 50mMultiple Airlines
Deal found 9/15$212
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/1011:41 amSWF - BWI
1 stop11h 51mMultiple Airlines
Sun 10/128:21 pmBWI - SWF
1 stop13h 50mMultiple Airlines
Deal found 9/16$278
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/1611:43 amSWF - IAD
1 stop7h 24mMultiple Airlines
Mon 10/2010:09 amIAD - SWF
1 stop9h 22mMultiple Airlines
Deal found 9/14$285
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/911:43 amSWF - BWI
1 stop7h 52mMultiple Airlines
Sun 10/128:21 pmBWI - SWF
1 stop13h 50mMultiple Airlines
Deal found 9/15$302
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/3011:43 amSWF - IAD
2 stops28h 51mMultiple Airlines
Mon 11/312:09 pmIAD - SWF
1 stop7h 07mMultiple Airlines
Deal found 9/15$322
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/1811:43 amSWF - BWI
1 stop27h 34mMultiple Airlines
Sat 9/204:24 pmBWI - SWF
1 stop18h 39mMultiple Airlines
Deal found 9/14$330
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/212:04 pmSWF - PHL
1 stop27h 41mMultiple Airlines
Wed 9/242:07 pmPHL - SWF
1 stop20h 56mMultiple Airlines
Deal found 9/14$341
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/1811:43 amSWF - PHL
2 stops23h 13mMultiple Airlines
Wed 9/242:07 pmPHL - SWF
1 stop20h 56mMultiple Airlines
Deal found 9/14$371
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/212:04 pmSWF - PHL
1 stop27h 41mMultiple Airlines
Thu 9/255:15 pmPHL - SWF
2 stops18h 29mMultiple Airlines
Deal found 9/14$381
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/1811:43 amSWF - PHL
1 stop12h 16mMultiple Airlines
Sat 9/208:43 pmPHL - SWF
1 stop14h 20mMultiple Airlines
Deal found 9/14$393
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/1811:43 amSWF - PHL
1 stop12h 16mMultiple Airlines
Thu 9/255:15 pmPHL - SWF
2 stops18h 29mMultiple Airlines
Deal found 9/14$413
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2412:24 pmSWF - IAD
2 stops8h 49mMultiple Airlines
Sat 10/259:38 pmIAD - SWF
1 stop13h 25mMultiple Airlines
Deal found 9/16$440

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 September 16, 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

Fri 10/3

12:11 pm-11:25 pm

1 stop11h 14m

Baltimore/Washington

Sun 10/5

8:21 pm-10:11 am

1 stop13h 50m

$212

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Fri 10/10

11:41 am-11:32 pm

1 stop11h 51m

Baltimore/Washington

Sun 10/12

8:21 pm-10:11 am

1 stop13h 50m

$278

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Thu 10/16

11:43 am-7:07 pm

1 stop7h 24m

Washington, D.C. Dulles Intl

Mon 10/20

10:09 am-7:31 pm

1 stop9h 22m

$285

New WindsorBaltimore

SWF - BWI

SWFBWI

New Windsor Stewart

Thu 10/9

11:43 am-7:35 pm

1 stop7h 52m

Baltimore/Washington

Sun 10/12

8:21 pm-10:11 am

1 stop13h 50m

$302

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Thu 10/30

11:43 am-4:34 pm

2 stops28h 51m

Washington, D.C. Dulles Intl

Mon 11/3

12:09 pm-7:16 pm

1 stop7h 07m

$322

New WindsorPhiladelphia

SWF - PHL

SWFPHL

New Windsor Stewart

Sun 9/21

2:04 pm-5:45 pm

1 stop27h 41m

Philadelphia

Wed 9/24

2:07 pm-11:03 am

1 stop20h 56m

$341

New WindsorPhiladelphia

SWF - PHL

SWFPHL

New Windsor Stewart

Sun 9/21

2:04 pm-5:45 pm

1 stop27h 41m

Philadelphia

Thu 9/25

5:15 pm-11:44 am

2 stops18h 29m

$381

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Fri 10/24

12:24 pm-9:13 pm

2 stops8h 49m

Washington, D.C. Dulles Intl

Sat 10/25

9:38 pm-11:03 am

1 stop13h 25m

$440

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Fri 10/10

11:41 am-11:29 pm

2 stops11h 48m

Washington, D.C. Dulles Intl

Mon 10/13

10:09 am-7:31 pm

1 stop9h 22m

$481

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Mon 11/24

10:57 am-10:50 am

2 stops23h 53m

Washington, D.C. Dulles Intl

Sun 11/30

5:26 pm-9:06 am

1 stop15h 40m

$493

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 39 results
1
2
3
4

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, August is the cheapest month in which you can book a flight from New Windsor to Maryland (average of $241). Flying from New Windsor to Maryland in March is currently the most expensive (average of $290). 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, August is the cheapest month in which you can book a flight from New Windsor to Maryland (average of $241). Flying from New Windsor to Maryland in March is currently the most expensive (average of $290). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Miami flights
LaGuardia to Dallas/Fort Worth flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to O'Hare Intl flights
Newark to Las Vegas flights
LaGuardia to O'Hare Intl flights
LaGuardia to Fort Lauderdale flights
Newark to O'Hare Intl flights
Newark to Miami flights
John F Kennedy Intl to Atlanta flights
John F Kennedy Intl to Orlando flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to Dallas/Fort Worth flights
John F Kennedy Intl to San Francisco flights
Newark to Los Angeles flights
LaGuardia to Miami flights
Newark to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Sky Harbor Intl flights
John F Kennedy Intl to Hobby flights
LaGuardia to Orlando flights
Newark to Hobby flights
John F Kennedy Intl to New Orleans flights
Newark to Sky Harbor Intl flights
Newark to San Francisco flights
LaGuardia to Los Angeles flights
John F Kennedy Intl to Denver flights
LaGuardia to Hobby flights
LaGuardia to Las Vegas flights
LaGuardia to Atlanta flights
LaGuardia to New Orleans flights
John F Kennedy Intl to George Bush Intcntl flights
John F Kennedy Intl to West Palm Beach flights
Newark to Denver flights
LaGuardia to Denver flights
Newark to Atlanta flights
John F Kennedy Intl to Austin flights
Newark to George Bush Intcntl flights
John F Kennedy Intl to Charlotte flights
John F Kennedy Intl to Seattle flights
Newark to West Palm Beach flights
John F Kennedy Intl to Ontario flights
John F Kennedy Intl to Nashville flights
Newark to New Orleans flights
John F Kennedy Intl to Honolulu flights
LaGuardia to Nashville flights
LaGuardia to Tampa flights
John F Kennedy Intl to Tampa flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.