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$59+ Cheap flights from New Windsor (SWF) to Orlando (MCO)

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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MCO
Aug 25 — Sep 11
Tue 8/25
Tue 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from New Windsor Stewart to Orlando are usually found in September or January, booked 17 days in advance, depart on a Wednesday or Thursday and return on a Thursday

Cheap flight deals from Stewart to Orlando

Cheapest flights from Stewart to Orlando
Explore the most affordable flight options available from Stewart to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Fri 9/1112:16 pm
SWF
-
MCO
1 stop4h 39m
Breeze Airways
Fri 9/256:00 am
MCO
-
SWF
1 stop4h 08m
Breeze Airways
Deal found 7/25$126
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.
Fri 9/1112:16 pm
SWF
-
MCO
1 stop4h 39m
Breeze Airways
Thu 9/177:20 am
MCO
-
SWF
Nonstop2h 56m
Breeze Airways
Deal found 7/23$128
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.
Fri 9/1112:16 pm
SWF
-
MCO
1 stop4h 39m
Breeze Airways
Sun 9/137:20 am
MCO
-
SWF
Nonstop2h 56m
Breeze Airways
Deal found 7/23$129
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Sun 9/610:33 am
SWF
-
MCO
Nonstop3h 06m
Breeze Airways
Sun 9/137:20 am
MCO
-
SWF
Nonstop2h 56m
Breeze Airways
Deal found 7/25$137
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Fri 9/1112:16 pm
SWF
-
MCO
1 stop4h 39m
Breeze Airways
Fri 9/187:20 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 7/25$141

Find flight deals from Stewart to Orlando

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Orlando (MCO). 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 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$126
(Kiwi.com)

One-way from

$59
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$235
Provider with most accurate pricing for New Windsor Stewart-Orlando flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Orlando flights.
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From New Windsor Stewart to Orlando
Search Deals
One-way flight from New Windsor Stewart to Orlando
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 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 Stewart to Orlando 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 26, 2026.
Use the filters below to find and compare flights from New Windsor to Orlando Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sat 10/3

12:39 pm-11:42 pm

1 stop11h 03m

Orlando

Sun 10/18

7:20 am-10:16 am

Nonstop2h 56m

$174

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 9/28

12:16 pm-4:55 pm

1 stop4h 39m

Orlando

Sun 10/4

7:20 am-10:16 am

Nonstop2h 56m

$181

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sat 10/24

12:39 pm-11:42 pm

1 stop11h 03m

Orlando

Sun 11/1

7:20 am-10:16 am

Nonstop2h 56m

$183
Quickest round-trip

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 10/15

10:56 am-2:15 pm

Nonstop3h 19m

Orlando

Sun 10/18

7:20 am-10:16 am

Nonstop2h 56m

$183

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Wed 9/23

12:39 pm-11:42 pm

1 stop11h 03m

Orlando

Mon 10/5

7:20 am-11:36 am

1 stop4h 16m

$198

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sat 8/29

12:05 pm-11:44 pm

1 stop11h 39m

Orlando

Sat 9/5

7:00 am-11:25 am

1 stop4h 25m

$204

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 9/21

12:16 pm-4:55 pm

1 stop4h 39m

Orlando

Sun 9/27

7:20 am-10:16 am

Nonstop2h 56m

$204

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Fri 9/25

10:48 am-2:59 pm

1 stop4h 11m

Orlando

Wed 9/30

7:05 am-11:39 am

1 stop4h 34m

$219

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 9/10

10:56 am-2:15 pm

Nonstop3h 19m

Orlando

Mon 9/14

7:20 am-11:36 am

1 stop4h 16m

$225

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 9/10

10:56 am-2:15 pm

Nonstop3h 19m

Orlando

Sat 9/19

7:05 am-11:39 am

1 stop4h 34m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Stewart to Orlando

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 Stewart to Orlando in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
OvagoPrice Accuracy3 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 New Windsor-Orlando Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Orlando Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Orlando Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Orlando Airport 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 New Windsor-Orlando Airport 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 Stewart to Orlando

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

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

To ensure you get the cheapest price possible for a flight from New Windsor to Orlando Airport, you should look to book at least 16 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 New Windsor to Orlando Airport?

Currently, September is the cheapest month in which you can book a flight from New Windsor to Orlando Airport (average of $159). Flying from New Windsor to Orlando Airport in December is currently the most expensive (average of $325). 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 SWF to MCO?

Find hourly flight availability from Stewart to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 26, 2026.

It’s typically best to fly out from New Windsor to Orlando Airport in the morning. Doing so could potentially save you 61% on the flight price compared to flying at noon, which is usually more expensive.

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

Airfare is below average for this route at the moment.

New Windsor to Orlando Airport flights typically cost between $218 and $296 in September.
The cheapest round-trip price found within the last 5 days was $126 on Breeze Airways (Sep 11-Sep 25).

Reviews of airlines servicing Orlando

Get insights into the airlines that provide service to Orlando. 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 Orlando. Reviews last updated July 26, 2026.
Read reviews from past customers who have flown Breeze Airways,JetBlue, andFrontier from New Windsor to Orlando Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
301 reviews

Comfort

8.2

Boarding

8.3

Crew

8.8

Overall

8.2

Entertainment

6.7

Food

6.7

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
301 reviews
Breeze Airways
8.2
Very good
301 reviews

Comfort

8.2

Boarding

8.3

Crew

8.8

Overall

8.2

Entertainment

6.7

Food

6.7

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.
JetBlue
7.1
Good
3,026 reviews
Breeze Airways
8.2
Very good
301 reviews

Comfort

8.2

Boarding

8.3

Crew

8.8

Overall

8.2

Entertainment

6.7

Food

6.7

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.
Frontier
5.6
Fair
2,761 reviews
Breeze Airways
8.2
Very good
301 reviews

Comfort

8.2

Boarding

8.3

Crew

8.8

Overall

8.2

Entertainment

6.7

Food

6.7

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 Stewart to Orlando. 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 from for flights from New Windsor to Orlando?

    New Windsor Stewart (SWF) is the airport you will fly out of if you book a flight from New Windsor to Orlando. You should not have trouble finding flights to Orlando from Stewart; the airport handles an average of 0 outbound flights to Orlando per day. You should also have plenty of airline options to choose from since 3 airlines have flights from the New Windsor airport to Orlando. It is only a 4.3 mi journey to Stewart (SWF) from New Windsor’s city center.

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

    A quick flight from New Windsor to Orlando Airport can take about 11h 03m. Breeze Airways provides one of the quickest options available for as low as $174. The distance from New Windsor to Orlando Airport is about 989 mi.

  • What are the cheapest airlines flying from New Windsor to Orlando Airport round-trip?

    Currently priced at $43, Frontier will fly you from New Windsor to Orlando Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Breeze Airways and JetBlue - these airlines can fly you to your destination from $148 and $177, respectively. Frontier is priced at 82% lower than the current average price of a flight leaving 3 months from now.

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

    Looking at all options, your cheapest flight can be booked for $76. While the most popular route (New Windsor Stewart - Orlando) can be booked for $137 on average, our data indicates $193 when flying from New Windsor to Orlando Airport.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from New Windsor to Orlando Airport (average of $159). Flying from New Windsor to Orlando Airport in December is currently the most expensive (average of $325). 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 Orlando Airport?

Book flights to Orlando Airport if you plan to visit one of these locations
Lake Buena Vista
Celebration
Titusville
Winter Haven
Four Corners
River Ranch
Sebastian
Leesburg
Clermont
Sanford
Apopka
Ormond Beach
Daytona Beach Shores
Lake Mary
Cocoa
Flagler Beach
Altamonte Springs
The Villages
Davenport
Haines City

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Top 3 airlines flying from Stewart to Orlando

Discover the top 3 airlines that operate flights from Stewart to Orlando. 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 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$43Average$148FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$148Average$245FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$177Average$237FlexibilityNo cancel feeOn-time62%

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