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Stewart

$304+ Cheap flights from Medford to New Windsor (MFR - 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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — SWF
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
1 adult, Economy
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Cheap flight deals from Medford to Stewart

One-way flights from Medford to Stewart
Search for one-way flight options from Medford to Stewart. Find affordable one-way fares based on user searches. Data last updated February 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/18. 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 3/299:20 pm
MFR
-
SWF
3 stops35h 32m
Multiple Airlines
Deal found 2/18$304
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Mon 3/237:50 pm
MFR
-
SWF
3 stops58h 49m
Multiple Airlines
Deal found 2/16$479
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Thu 4/99:12 pm
MFR
-
SWF
3 stops58h 43m
Multiple Airlines
Deal found 2/16$544
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/211:22 pm
MFR
-
SWF
3 stops40h 35m
Multiple Airlines
Deal found 2/16$899

Find flight deals from Medford to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Medford (MFR) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

November

Cheapest in

February

Average price

$389
Provider with most accurate pricing for Medford-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Medford-New York (NYC) flights.
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($138 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($29 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 Medford 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 20, 2026.
Use the filters below to find and compare flights from Medford to New Windsor that are best for you.

Fly from

Medford

Fly to

Stewart

Route

Depart

Return

Price

MedfordNew Windsor

MFR - SWF

MFRSWF

Medford

Sun 3/29

9:20 pm-11:52 am

3 stops35h 32m

$304

MedfordNew Windsor

MFR - SWF

MFRSWF

Medford

Mon 3/23

7:50 pm-9:39 am

3 stops58h 49m

$479

MedfordNew Windsor

MFR - SWF

MFRSWF

Medford

Thu 4/9

9:12 pm-10:55 am

3 stops58h 43m

$544

MedfordNew Windsor

MFR - SWF

MFRSWF

Medford

Sat 3/21

1:22 pm-8:57 am

3 stops40h 35m

$899

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Best time to book a flight from Medford to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Medford 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 Medford to New Windsor

What is the cheapest month to book a flight from Medford to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Medford to New Windsor (average of $344). Flying from Medford to New Windsor in July is currently the most expensive (average of $819). 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 Medford to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Medford to Stewart that include hotel bookings?

    Yes. In addition to deals on Medford to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Medford to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Medford to Stewart.

  • Can I find deals for business class flights from Medford to Stewart?

    Yes. Cheapflights offers flight deals from Medford 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 Medford to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Medford to New Windsor (average of $344). Flying from Medford to New Windsor in July is currently the most expensive (average of $819). 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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