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Stewart

$408+ Cheap flights from Helena to New Windsor (HLN - 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — SWF
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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Cheap flight deals from Helena to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Helena (HLN) 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 January 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars
Provider with most accurate pricing for Helena-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Helena-New York (NYC) flights.
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Find flight deals from Helena to Stewart

One-way flights from Helena to Stewart
Search for one-way flight options from Helena to Stewart. Find affordable one-way fares based on user searches. Data last updated January 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/10. 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 2/284:36 pm
HLN
-
SWF
3 stops39h 37m
Multiple Airlines
Deal found 1/10$408
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 3/144:36 pm
HLN
-
SWF
3 stops38h 26m
Multiple Airlines
Deal found 1/10$469

Cheapflights Fare Finder

 
Customize your flight search to find flights from Helena 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 January 12, 2026.
Use the filters below to find and compare flights from Helena to New Windsor that are best for you.

Fly from

Helena

Fly to

Stewart

Route

Depart

Return

Price

HelenaNew Windsor

HLN - SWF

HLNSWF

Helena

Sat 2/28

4:36 pm-10:13 am

3 stops39h 37m

$408

HelenaNew Windsor

HLN - SWF

HLNSWF

Helena

Sat 3/14

4:36 pm-9:02 am

3 stops38h 26m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Best time to book a flight from Helena to Stewart

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

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

Currently, February is the cheapest month in which you can book a flight from Helena to New Windsor (average of $106). Flying from Helena to New Windsor in May is currently the most expensive (average of $293). 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 Helena 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 Helena to Stewart that include hotel bookings?

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Helena to New Windsor (average of $106). Flying from Helena to New Windsor in May is currently the most expensive (average of $293). 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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