$162+ Cheap flights from New Windsor

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 21/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
SWF — MSY
30 Apr — 7 May1
1 adult
1 adult, Economy, 0 bags

Find flights from Stewart within your budget

 
Find flights departing from Stewart that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 31 March 2026. In the last 7 days, Cheapflights users made a total of 647,157 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 23/4

11:48-15:07

Nonstop3h 19m

Orlando

Thu 30/4

08:10-11:08

Nonstop2h 58m

$296

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 3/8

12:17-16:51

1 stop4h 34m

Orlando

Sat 8/8

07:00-11:25

1 stop4h 25m

$359

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sat 15/8

12:05-23:59

1 stop11h 54m

Orlando

Sat 22/8

07:00-11:25

1 stop4h 25m

$362

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 16/4

11:48-15:07

Nonstop3h 19m

Orlando

Sun 19/4

08:10-11:08

Nonstop2h 58m

$376

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 6/8

09:38-12:44

Nonstop3h 06m

Orlando

Sat 15/8

07:00-11:25

1 stop4h 25m

$398

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Wed 1/7

12:05-23:59

1 stop11h 54m

Orlando

Wed 8/7

07:00-11:25

1 stop4h 25m

$424

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 19/4

11:48-15:07

Nonstop3h 19m

Orlando

Sun 26/4

08:10-11:08

Nonstop2h 58m

$435

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Tue 30/6

11:48-14:54

Nonstop3h 06m

Orlando

Wed 8/7

07:00-11:25

1 stop4h 25m

$503
Cheapest one-way
Fastest single journey

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 21/9

12:26-17:05

1 stop4h 39m

$162

New WindsorDenver

SWF - DEN

SWFDEN

New Windsor Stewart

Thu 11/6

09:38-00:29

2 stops16h 51m

$626

Flights are sorted by cheapest return flights first.

Deals found on 26/3

Sorted by cheapest first

Best time to book a flight from Stewart

Have a flexible travel schedule? Discover the best time to fly from Stewart with our price prediction graph.
Estimated return 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.

Travel insights for flights from Stewart

Get recent, data-driven insights about flights from Stewart including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from New Windsor (average of $101). Flying from New Windsor in March will prove the most costly (average of $165). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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Related info for your journey

Access useful and relevant information related to your journey from Stewart. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 31 March 2026.

  • What are the most popular destinations to fly to from New Windsor?

    For the current month, the most popular flights from New Windsor are Fort Lauderdale, Orlando, Orlando Sanford Intl Airport. Myrtle Beach, Fort Lauderdale, Orlando are the most popular locations from New Windsor year round.

  • What is the cheapest month to fly from New Windsor?

    Currently, the cheapest month for flights from New Windsor is September. The most expensive month for flights is March. The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

  • Where are the cheapest places to fly to from New Windsor?

    View the cheapest flight destinations from New Windsor:
    Fly from New Windsor to New Orleans from $242 round trip

  • How does Cheapflights help users find flights from Stewart?

    Deals for flights from Stewart are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.

  • Why should you use Cheapflights to find cheap flight tickets from Stewart?

    Cheapflights helps you find that perfect flight from Stewart by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

  • Can Cheapflights find flights from Stewart with no change fees?

    Yes, we can. To see specific flights from Stewart with no change fees, users can toggle flexible booking options after using the search form above to find flights.

  • Can Cheapflights notify me if prices for flights from Stewart become cheaper?

    Yes, Cheapflights offers price alerts on flights from Stewart so you can book your travels when it’s right. The Price Alerts feature is available by clicking the bell icon next to the flight deals above and providing your email address.

See more FAQs

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Stewart?

Deals for flights from Stewart are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Stewart?

Cheapflights helps you find that perfect flight from Stewart by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Stewart with no change fees?

Yes, we can. To see specific flights from Stewart with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Stewart become cheaper?

Yes, Cheapflights offers price alerts on flights from Stewart so you can book your travels when it’s right. The Price Alerts feature is available by clicking the bell icon next to the flight deals above and providing your email address.

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