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Stewart

$68+ Cheap flights from Orlando (MCO) to New Windsor (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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SWF
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheap flight deals from Orlando to Stewart

Cheapest flights from Orlando to Stewart
Explore the most affordable flight options available from Orlando to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/23. 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 9/107:20 am
MCO
-
SWF
Nonstop2h 56m
Breeze Airways
Fri 9/1112:16 pm
SWF
-
MCO
1 stop4h 39m
Breeze Airways
Deal found 7/23$129
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/276:55 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Fri 9/1112:16 pm
SWF
-
MCO
1 stop4h 39m
Breeze Airways
Deal found 7/27$138
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Tue 9/18:10 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Fri 9/1112:16 pm
SWF
-
MCO
1 stop4h 39m
Breeze Airways
Deal found 7/27$143
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 9/107:20 am
MCO
-
SWF
Nonstop2h 56m
Breeze Airways
Wed 9/1612:39 pm
SWF
-
MCO
1 stop11h 03m
Breeze Airways
Deal found 7/24$145
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/276:55 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Sun 9/610:33 am
SWF
-
MCO
Nonstop3h 06m
Breeze Airways
Deal found 7/27$147
This Flightnetwork deal was found by Cheapflights users on 7/22. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:20 am
MCO
-
SWF
Nonstop2h 56m
Breeze Airways
Sat 9/1212:39 pm
SWF
-
MCO
1 stop11h 03m
Breeze Airways
Deal found 7/22$149
This CheapOair deal was found by Cheapflights users on 7/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:20 am
MCO
-
SWF
Nonstop2h 56m
Breeze Airways
Wed 9/3012:39 pm
SWF
-
MCO
1 stop11h 03m
Breeze Airways
Deal found 7/23$151
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Tue 9/18:10 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Sun 9/610:33 am
SWF
-
MCO
Nonstop3h 06m
Breeze Airways
Deal found 7/27$152

Find flight deals from Orlando to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (MCO) 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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$129
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$292
Provider with most accurate pricing for Orlando-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando-New Windsor Stewart flights.
Search Deals
From Orlando to New Windsor Stewart
Search Deals
One-way flight from Orlando to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando 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 July 27, 2026.
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 - SWF

MCOSWF

Orlando

Thu 9/3

6:55 am-9:53 am

Nonstop2h 58m

New Windsor Stewart

Fri 9/11

12:16 pm-4:55 pm

1 stop4h 39m

$153

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 9/10

7:20 am-10:16 am

Nonstop2h 56m

New Windsor Stewart

Thu 9/17

10:56 am-2:15 pm

Nonstop3h 19m

$187

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 9/10

7:20 am-10:16 am

Nonstop2h 56m

New Windsor Stewart

Sun 9/13

10:56 am-2:15 pm

Nonstop3h 19m

$188

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 9/24

7:20 am-10:16 am

Nonstop2h 56m

New Windsor Stewart

Sun 9/27

10:56 am-2:15 pm

Nonstop3h 19m

$193

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Tue 8/11

8:10 am-11:08 am

Nonstop2h 58m

New Windsor Stewart

Sat 8/15

12:05 pm-11:44 pm

1 stop11h 39m

$221

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 9/17

7:20 am-10:16 am

Nonstop2h 56m

New Windsor Stewart

Fri 9/18

12:16 pm-4:55 pm

1 stop4h 39m

$226
Quickest round-trip

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 8/20

6:55 am-9:53 am

Nonstop2h 58m

New Windsor Stewart

Tue 8/25

11:48 am-2:54 pm

Nonstop3h 06m

$246

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 9/17

7:20 am-10:16 am

Nonstop2h 56m

New Windsor Stewart

Mon 9/21

12:16 pm-4:55 pm

Nonstop4h 39m

$255

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 7/30

6:55 am-9:53 am

Nonstop2h 58m

New Windsor Stewart

Sat 8/8

12:05 pm-11:44 pm

1 stop11h 39m

$256

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Sun 8/9

6:55 am-9:53 am

Nonstop2h 58m

New Windsor Stewart

Sun 8/16

10:33 am-1:39 pm

Nonstop3h 06m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

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

Compare providers for flights from Orlando to Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Orlando to Stewart in July.
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
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 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 $130). Flying from Orlando Airport to New Windsor in December is currently the most expensive (average of $500). 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?

Find hourly flight availability from Orlando to Stewart. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 27, 2026.

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 $172 and $351 in September.
The cheapest round-trip price found within the last 5 days was $129 on Breeze Airways (Sep 10-Sep 11).

Reviews of airlines servicing Stewart

Get insights into the airlines that provide service to Stewart. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Stewart. Reviews last updated July 27, 2026.
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
302 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.7

Food

6.7

Crew

8.8

Overall

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.2
Very good
302 reviews
Breeze Airways
8.2
Very good
302 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.7

Food

6.7

Crew

8.8

Overall

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

Related info for your journey

Find useful and relevant information for your journey from Orlando to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 $153, Breeze Airways can have you in New Windsor from Orlando Airport in 2h 58m. 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 $130. Breeze Airways is priced at 50% 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 $229, our data shows the cheapest flight currently is $84. When looking at the most popular route, (Orlando - New Windsor Stewart), you can expect to pay $158 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 $130). Flying from Orlando Airport to New Windsor in December is currently the most expensive (average of $500). 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

Discover the top airline that operate flights from Orlando to Stewart. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$130Average$255FlexibilityNo cancel feeOn-timeN/A

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