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Stewart

$66+ Cheap flights from Orlando (MCO) to New Windsor (SWF)

MCO — SWF
Dec 10 — Dec 171
Thu 12/10
Thu 12/17
1 adult, Economy
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Cheap flight deals from Orlando to Stewart

Cheapest flights from Orlando to Stewart

Thu 12/37:30 am -
Nonstop2h 56m
Sat 12/512:29 pm -
1 stop11h 13m
Deal found 11/8$159
Thu 12/107:30 am -
Nonstop2h 56m
Sat 12/1212:29 pm -
1 stop11h 13m
Deal found 11/9$164
Fri 12/47:20 am -
1 stop4h 16m
Sat 12/512:29 pm -
1 stop11h 13m
Deal found 11/6$168
Wed 12/27:05 am -
1 stop4h 44m
Sat 12/512:29 pm -
1 stop11h 13m
Deal found 11/5$172
Thu 12/107:30 am -
Nonstop2h 56m
Mon 12/1412:16 pm -
1 stop4h 39m
Deal found 11/10$173

Find flight deals from Orlando to Stewart

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$157
(Travelocity)

One-way from

$66
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$306
Provider with most accurate pricing for Orlando-New Windsor Stewart flight deals.
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Provider most trusted by Cheapflights users for Orlando-New Windsor Stewart flights.
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From Orlando to New Windsor Stewart
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One-way flight from Orlando to New Windsor Stewart
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Highest demand for flights based on searches. 2% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in November 2026
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Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoNew Windsor

MCO Orlando - SWF New Windsor Stewart

MCOSWF

Orlando

Fri 1/29

6:30 am-10:57 am

1 stop4h 27m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$68
Quickest round-trip

OrlandoNew Windsor

MCO Orlando - SWF New Windsor Stewart

MCOSWF

Orlando

Thu 12/10

7:30 am-10:26 am

Nonstop2h 56m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$94

OrlandoNew Windsor

MCO Orlando - SWF New Windsor Stewart

MCOSWF

Orlando

Sat 1/16

7:00 am-11:49 am

1 stop4h 49m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$100

OrlandoNew Windsor

MCO Orlando - SWF New Windsor Stewart

MCOSWF

Orlando

Tue 12/8

7:07 pm-11:49 am

1 stop16h 42m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$121

OrlandoNew Windsor

MCO Orlando - SWF New Windsor Stewart

MCOSWF

Orlando

Fri 12/25

7:20 am-11:36 am

1 stop4h 16m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$126

OrlandoNew Windsor

MCO Orlando - SWF New Windsor Stewart

MCOSWF

Orlando

Thu 12/24

7:10 am-11:36 am

1 stop28h 26m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$129

OrlandoNew Windsor

MCO Orlando - SWF New Windsor Stewart

MCOSWF

Orlando

Mon 12/14

7:20 am-11:36 am

1 stop4h 16m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$158

OrlandoNew Windsor

MCO Orlando - SWF New Windsor Stewart

MCOSWF

Orlando

Thu 5/6

7:10 am-10:09 am

Nonstop2h 59m

New Windsor Stewart

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$177

OrlandoNew Windsor

MCO Orlando - SWF New Windsor Stewart

MCOSWF

Orlando

Thu 1/21

7:20 am-10:16 am

Nonstop2h 56m

New Windsor Stewart

Sun 1/24

10:56 am-2:15 pm

Nonstop3h 19m

$178

OrlandoNew Windsor

MCO Orlando - SWF New Windsor Stewart

MCOSWF

Orlando

Thu 12/10

7:30 am-10:26 am

Nonstop2h 56m

New Windsor Stewart

Mon 12/14

12:16 pm-4:55 pm

1 stop4h 39m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Orlando to Stewart

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Orlando to Stewart in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy2 starsTrust Score*3 stars
MytripPrice Accuracy2 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 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 Airport-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando Airport-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando 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 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 to Stewart

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

Cheapflights Insights

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

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

Currently, January is the cheapest month in which you can book a flight from Orlando Airport to New Windsor (average of $194). Flying from Orlando Airport to New Windsor in June is currently the most expensive (average of $355). 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 MCO to SWF?

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

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

Airfare is below average for this route at the moment.

Orlando Airport to New Windsor flights typically cost between $268 and $451 in January.
The cheapest round-trip price found within the last 5 days was $157 on Breeze Airways (Jan 21-Jan 27).

Reviews of airlines servicing Stewart

Read through reviews of airlines operating flights from Orlando Airport to New Windsor, such as Breeze Airways. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
323 reviews

Crew

8.8

Entertainment

6.8

Boarding

8.4

Comfort

8.2

Food

6.7

Overall

8.2

Reviews

1 / 17
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
Breeze Airways
8.2
Very good
323 reviews
Breeze Airways
8.2
Very good
323 reviews

Crew

8.8

Entertainment

6.8

Boarding

8.4

Comfort

8.2

Food

6.7

Overall

8.2

Reviews

1 / 17
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.

Related info for your journey

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

    New Windsor Stewart (SWF), located 4.3 mi from the city center, is the airport you fly into when you book flights from Orlando to New Windsor. 1 airline have flights to Stewart from Orlando on a regular basis. Booking flights from Orlando to New Windsor Stewart should not be difficult; the airport handles an average of 0 inbound flights from Orlando per day.

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

    For as low as $178, Breeze Airways can have you in New Windsor from Orlando Airport in 2h 56m. The distance between Orlando Airport and New Windsor is about 989 mi. Most flights are nonstop.

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

    Cheapflights users have booked flights from Orlando Airport to New Windsor round-trip from $162. Breeze Airways is priced at 42% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest flights from Orlando Airport to New Windsor?

    While on average a flight from Orlando Airport to New Windsor is generally $161, our data shows the cheapest flight currently is $69. When looking at the most popular route, (Orlando - New Windsor Stewart), you can expect to pay $190 for that flight.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Orlando Airport to New Windsor (average of $194). Flying from Orlando Airport to New Windsor in June is currently the most expensive (average of $355). 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 to Stewart

AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$162Average$270FlexibilityNo cancel feeOn-timeN/A

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