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Stewart

$44+ Cheap flights from Orlando Sanford Intl (SFB) to New Windsor (SWF)

SFB — SWF
Oct 9 — Oct 161
Fri 10/9
Fri 10/16
1 adult, Economy
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Find cheap flights from Orlando Sanford Intl to Stewart with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Orlando Sanford Intl to New Windsor Stewart are usually found in January or October, booked 82 days in advance, depart on a Tuesday or Thursday and return on a Monday

Cheap flight deals from Orlando Sanford Intl to Stewart

Cheapest flights from Orlando Sanford Intl to Stewart

Fri 11/131:54 pm -
Nonstop2h 46m
Mon 11/167:04 pm -
Nonstop2h 49m
Deal found 9/9$81
Fri 12/47:30 am -
Nonstop2h 43m
Fri 12/1111:03 am -
Nonstop2h 49m
Deal found 9/7$98
Mon 11/23:25 pm -
Nonstop2h 46m
Mon 11/97:04 pm -
Nonstop2h 49m
Deal found 9/6$100
Fri 12/47:30 am -
Nonstop2h 43m
Mon 12/711:03 am -
Nonstop2h 49m
Deal found 9/8$104
Fri 11/61:54 pm -
Nonstop2h 46m
Mon 11/97:04 pm -
Nonstop2h 49m
Deal found 9/9$108

Find flight deals from Orlando Sanford Intl to Stewart

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$81
(CheapOair)

One-way from

$51
(CheapOair)

Popular in

April

Cheapest in

January

Average price

$137
Provider with most accurate pricing for Orlando Sanford Intl-New Windsor Stewart flight deals.
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Provider most trusted by Cheapflights users for Orlando Sanford Intl-New Windsor Stewart flights.
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From Orlando Sanford Intl to New Windsor Stewart
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One-way flight from Orlando Sanford Intl to New Windsor Stewart
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Highest demand for flights based on searches. 12% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Orlando Sanford Intl Airport to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoNew Windsor

SFB Orlando Sanford Intl - SWF New Windsor Stewart

SFBSWF

Orlando Sanford Intl

Fri 9/25

7:30 am-10:16 am

Nonstop2h 46m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$62

OrlandoNew Windsor

SFB Orlando Sanford Intl - SWF New Windsor Stewart

SFBSWF

Orlando Sanford Intl

Fri 11/13

1:54 pm-4:40 pm

Nonstop2h 46m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$63

OrlandoNew Windsor

SFB Orlando Sanford Intl - SWF New Windsor Stewart

SFBSWF

Orlando Sanford Intl

Fri 11/13

1:54 pm-4:40 pm

Nonstop2h 46m

New Windsor Stewart

Mon 11/16

7:04 pm-9:53 pm

Nonstop2h 49m

$81

OrlandoNew Windsor

SFB Orlando Sanford Intl - SWF New Windsor Stewart

SFBSWF

Orlando Sanford Intl

Mon 9/28

7:45 am-10:31 am

Nonstop2h 46m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$88

OrlandoNew Windsor

SFB Orlando Sanford Intl - SWF New Windsor Stewart

SFBSWF

Orlando Sanford Intl

Fri 11/6

1:54 pm-4:40 pm

Nonstop2h 46m

New Windsor Stewart

Mon 11/9

7:04 pm-9:53 pm

Nonstop2h 49m

$94

OrlandoNew Windsor

SFB Orlando Sanford Intl - SWF New Windsor Stewart

SFBSWF

Orlando Sanford Intl

Mon 12/14

7:30 am-10:13 am

Nonstop2h 43m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$95

OrlandoNew Windsor

SFB Orlando Sanford Intl - SWF New Windsor Stewart

SFBSWF

Orlando Sanford Intl

Fri 12/11

7:30 am-10:13 am

Nonstop2h 43m

New Windsor Stewart

Mon 12/14

11:03 am-1:52 pm

Nonstop2h 49m

$113

OrlandoNew Windsor

SFB Orlando Sanford Intl - SWF New Windsor Stewart

SFBSWF

Orlando Sanford Intl

Mon 10/26

3:25 pm-6:11 pm

Nonstop2h 46m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$126

OrlandoNew Windsor

SFB Orlando Sanford Intl - SWF New Windsor Stewart

SFBSWF

Orlando Sanford Intl

Fri 10/2

5:12 pm-7:58 pm

Nonstop2h 46m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$127

OrlandoNew Windsor

SFB Orlando Sanford Intl - SWF New Windsor Stewart

SFBSWF

Orlando Sanford Intl

Mon 9/14

7:45 am-10:31 am

Nonstop2h 46m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/5

Showing 1-10 of 21 resultsSorted by cheapest first
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Compare providers for flights from Orlando Sanford Intl to Stewart

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Orlando Sanford Intl to Stewart in September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Orlando Sanford Intl Airport-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando Sanford Intl Airport-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando Sanford Intl Airport-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando Sanford Intl Airport-New Windsor flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Orlando Sanford Intl Airport-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Orlando Sanford Intl to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Orlando Sanford Intl with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Orlando Sanford Intl Airport to New Windsor

How far ahead should I book a flight from Orlando Sanford Intl Airport to New Windsor?

To ensure you get the cheapest price possible for a flight from Orlando Sanford Intl Airport to New Windsor, you should look to book at least 68 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Orlando Sanford Intl Airport to New Windsor?

Currently, January is the cheapest month in which you can book a flight from Orlando Sanford Intl Airport to New Windsor (average of $120). Flying from Orlando Sanford Intl Airport to New Windsor in April is currently the most expensive (average of $250). 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.

What is the cheapest time of day to fly from SFB to SWF?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Orlando Sanford Intl Airport to New Windsor as you normally would.

How much does it cost to fly round-trip from Orlando Sanford Intl Airport to New Windsor?

Airfare is below average for this route at the moment.

Orlando Sanford Intl Airport to New Windsor flights typically cost between $100 and $257 in November.
The cheapest round-trip price found within the last 5 days was $81 on Allegiant Air (Nov 13-Nov 16).

Reviews of airlines servicing Stewart

Get a feel of what it's like to fly with Allegiant Air from Orlando Sanford Intl Airport to New Windsor by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Allegiant Air
7.3
Good
679 reviews

Entertainment

5.4

Overall

7.3

Boarding

7.7

Crew

8.1

Comfort

6.9

Food

5.9

Reviews

1 / 20
2.0
Mediocre

Nic,Aug 2026

SRQ - ALB

Worker at gate refused to let me measure my personal item and insisted it needed to be a carryon and to pay 75$. I understand if it’s too big but she wouldn’t even let me go measure it. She eventually let me measure my own luggage after back n forth. It is a few inches too big and she comes over and attempts to grab my suitcase out my hands and I pull it away from her. She then shuts the door of the gate and says to call the police. I then just offer to pay for the carryon and she says ok. Then refuses to use let me use my tap to pay, luckily I had my physical card on me. As soon as I walked out the door I respectfully asked for her name. She began screaming at me and threatening me. This worker was just so hostile I understand if my stuffs too big I will pay the difference I’m not trying to get over on the rules. I was confused because I was allowed to board my destination flight with this item as a personal item. So I was confused by this whole situation from the go. It also caused a massive scene at the airport and I was extremely embarrassed. It genuinely seemed like this worker was out to get me for some reason. I had literally just arrived to the gate as it was already boarding so I hadn’t done anything prior. Super weird situation and it really spooked me.
Allegiant Air
7.3
Good
679 reviews
Allegiant Air
7.3
Good
679 reviews

Entertainment

5.4

Overall

7.3

Boarding

7.7

Crew

8.1

Comfort

6.9

Food

5.9

Reviews

1 / 20
2.0
Mediocre

Nic,Aug 2026

SRQ - ALB

Worker at gate refused to let me measure my personal item and insisted it needed to be a carryon and to pay 75$. I understand if it’s too big but she wouldn’t even let me go measure it. She eventually let me measure my own luggage after back n forth. It is a few inches too big and she comes over and attempts to grab my suitcase out my hands and I pull it away from her. She then shuts the door of the gate and says to call the police. I then just offer to pay for the carryon and she says ok. Then refuses to use let me use my tap to pay, luckily I had my physical card on me. As soon as I walked out the door I respectfully asked for her name. She began screaming at me and threatening me. This worker was just so hostile I understand if my stuffs too big I will pay the difference I’m not trying to get over on the rules. I was confused because I was allowed to board my destination flight with this item as a personal item. So I was confused by this whole situation from the go. It also caused a massive scene at the airport and I was extremely embarrassed. It genuinely seemed like this worker was out to get me for some reason. I had literally just arrived to the gate as it was already boarding so I hadn’t done anything prior. Super weird situation and it really spooked me.

Related info for your journey

  • What airport do you fly into for flights to New Windsor from Orlando Sanford Intl?

    New Windsor Stewart (SWF) is the airport you will fly into if you book a flight from Orlando Sanford Intl to New Windsor. You should not have trouble finding flights to Stewart from Orlando Sanford Intl; the airport handles an average of 0 inbound flights from Orlando Sanford Intl per day. You should also have plenty of airline options to choose from since 1 airline has flights to the New Windsor airport from Orlando Sanford Intl. It is only a 4.3 mi journey from Stewart (SWF) to New Windsor’s city center.

  • How long is the flight from Orlando Sanford Intl Airport to New Windsor?

    Airlines like Allegiant Air fly from Orlando Sanford Intl Airport to New Windsor in about 2h 46m. The time it takes to get you to your destination is usually consistent. Airlines will cover a distance of 966 mi. Generally, flights for this route are nonstop.

  • What is the cheapest airline to fly from Orlando Sanford Intl Airport to New Windsor round-trip?

    Our cheapest airline available from Orlando Sanford Intl Airport to New Windsor is Allegiant Air. Our recent data shows that you can find tickets from as low as $94 on this airline. Allegiant Air is priced at 42% lower than the current average price of a flight leaving 3 months from now.

  • Can I find deals for flights from Orlando Sanford Intl to Stewart that include hotel bookings?

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

  • How can I find direct flights from Orlando Sanford Intl to Stewart?

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

  • Can I find deals for business class flights from Orlando Sanford Intl to Stewart?

    Yes. Cheapflights offers flight deals from Orlando Sanford Intl 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 Orlando Sanford Intl Airport to New Windsor?

    Currently, January is the cheapest month in which you can book a flight from Orlando Sanford Intl Airport to New Windsor (average of $120). Flying from Orlando Sanford Intl Airport to New Windsor in April is currently the most expensive (average of $250). 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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Top airline flying from Orlando Sanford Intl to Stewart

AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$94Average$155FlexibilityNo cancel feeOn-time88%

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