HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Orlando

$58+ Cheap flights from New Windsor (SWF) to Orlando (ORL)

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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORL
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Orlando with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from New Windsor Stewart to Orlando are usually found in May or January, booked 48 days in advance, depart on a Monday or Friday and return on a Friday

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 May 6, 2026.

This Gotogate deal was found by Cheapflights users on 5/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/309:38 am
SWF
-
MCO
Nonstop3h 06m
Breeze Airways
Thu 9/36:00 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Deal found 5/2$123
This Mytrip deal was found by Cheapflights users on 5/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/309:38 am
SWF
-
MCO
Nonstop3h 06m
Breeze Airways
Sun 9/66:00 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Deal found 5/2$126
This Mytrip deal was found by Cheapflights users on 5/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:17 pm
SWF
-
MCO
1 stop4h 34m
Breeze Airways
Sun 9/66:00 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Deal found 5/4$127
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 9/69:38 am
SWF
-
MCO
Nonstop3h 06m
Breeze Airways
Sun 9/136:00 am
MCO
-
SWF
Nonstop2h 56m
Breeze Airways
Deal found 5/5$132
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 8/2511:48 am
SWF
-
MCO
Nonstop3h 06m
Breeze Airways
Sun 9/136:00 am
MCO
-
SWF
Nonstop2h 56m
Breeze Airways
Deal found 5/4$133
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 8/309:38 am
SWF
-
MCO
Nonstop3h 06m
Breeze Airways
Wed 9/97:00 am
MCO
-
SWF
1 stop4h 39m
Breeze Airways
Deal found 5/4$134
This Gotogate deal was found by Cheapflights users on 5/4. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:05 pm
SWF
-
MCO
1 stop11h 54m
Breeze Airways
Wed 8/127:00 am
MCO
-
SWF
1 stop4h 25m
Breeze Airways
Deal found 5/4$136

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 (ORL). 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 May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$123
(Gotogate)

One-way from

$58
(Booking.com)

Popular in

March

Cheapest in

May

Average price

$151
Provider with most accurate pricing for New Windsor Stewart-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Orlando (ORL) flights.
Search Deals
From New Windsor Stewart to Orlando (ORL)
Search Deals
One-way flight from New Windsor Stewart to Orlando (ORL)
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($75 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 6, 2026.
Use the filters below to find and compare flights from New Windsor to Orlando 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 6/13

12:05 pm-11:59 pm

1 stop11h 54m

Orlando

Tue 6/23

8:10 am-11:08 am

Nonstop2h 58m

$147

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Wed 6/17

12:05 pm-5:02 pm

1 stop4h 57m

Orlando

Tue 6/23

8:10 am-11:08 am

Nonstop2h 58m

$156

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sat 5/23

12:05 pm-11:59 pm

1 stop11h 54m

Orlando

Wed 5/27

7:00 am-11:25 am

1 stop4h 25m

$185

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sat 5/16

12:05 pm-11:59 pm

1 stop11h 54m

Orlando

Wed 5/20

7:00 am-11:25 am

1 stop4h 25m

$187

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Wed 7/8

12:05 pm-11:59 pm

1 stop11h 54m

Orlando

Sat 7/11

7:00 am-11:25 am

1 stop4h 25m

$210

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sat 5/16

12:05 pm-11:59 pm

1 stop11h 54m

Orlando

Sat 5/23

7:00 am-11:25 am

1 stop4h 25m

$234

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 8/3

12:17 pm-4:51 pm

1 stop4h 34m

Orlando

Sat 8/8

7:00 am-11:25 am

1 stop4h 25m

$237
Quickest round-trip

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 5/17

9:38 am-12:44 pm

Nonstop3h 06m

Orlando

Thu 6/4

6:00 am-8:58 am

Nonstop2h 58m

$241

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sat 7/11

12:05 pm-11:59 pm

1 stop11h 54m

Orlando

Sat 7/25

7:00 am-11:25 am

1 stop4h 25m

$243

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 5/11

12:17 pm-4:51 pm

1 stop4h 34m

Orlando

Sun 5/17

6:00 am-8:58 am

Nonstop2h 58m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 21 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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice 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 New Windsor-Orlando 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Orlando flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Orlando 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 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

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

The best time to book flights from New Windsor to Orlando is 75 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, September is the cheapest month in which you can book a flight from New Windsor to Orlando (average of $43). Flying from New Windsor to Orlando in December is currently the most expensive (average of $100). 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 ORL?

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 May 6, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 58% on flights from New Windsor to Orlando by exploring options for tickets in the evening.

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

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 May 6, 2026.
Read through reviews of airlines operating flights from New Windsor to Orlando, such as Breeze Airways,Allegiant Air, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
283 reviews

Comfort

8.2

Boarding

8.3

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.6

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
8.1
Very good
283 reviews
Breeze Airways
8.1
Very good
283 reviews

Comfort

8.2

Boarding

8.3

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.6

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.
Allegiant Air
7.3
Good
708 reviews
Breeze Airways
8.1
Very good
283 reviews

Comfort

8.2

Boarding

8.3

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.6

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
2,978 reviews
Breeze Airways
8.1
Very good
283 reviews

Comfort

8.2

Boarding

8.3

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.6

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.
Spirit Airlines
6.3
Okay
8,638 reviews
Breeze Airways
8.1
Very good
283 reviews

Comfort

8.2

Boarding

8.3

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.6

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), located 4.3 mi from the city center, is the airport you fly out of when you book flights from New Windsor to Orlando. 4 airlines have flights from Stewart to Orlando on a regular basis. Booking flights from New Windsor Stewart to Orlando should not be difficult; the airport handles an average of 0 outbound flights to Orlando per day.

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

    A quick flight from New Windsor to Orlando can take about 11h 54m. Breeze Airways provides one of the quickest options available for as low as $147. The distance from New Windsor to Orlando is about 989 mi.

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

    Flying on Spirit Airlines is currently your cheapest option to Orlando, with prices starting at $55. Additional round-trip tickets that might be worth considering are offered by Allegiant Air and Breeze Airways, with the lowest prices starting at $81 and $127, respectively. Users have found that Spirit Airlines is 75% cheaper than the other options available to this destination.

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

    Looking at all options, your cheapest flight can be booked for $72. While the most popular route (New Windsor Stewart - Orlando) can be booked for $130 on average, our data indicates $181 when flying from New Windsor to Orlando.

  • 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?

    Currently, September is the cheapest month in which you can book a flight from New Windsor to Orlando (average of $43). Flying from New Windsor to Orlando in December is currently the most expensive (average of $100). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Orlando

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to Miami flights
LaGuardia to Fort Lauderdale flights
Newark to Orlando flights
Newark to Miami flights
John F Kennedy Intl to Fort Lauderdale flights
LaGuardia to Orlando flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to West Palm Beach flights
Newark to Tampa flights
Newark to West Palm Beach flights
White Plains to Orlando flights
LaGuardia to Tampa flights
John F Kennedy Intl to Tampa flights
LaGuardia to West Palm Beach flights
Newark to Jacksonville flights
Newark to Fort Myers flights
LaGuardia to Fort Myers flights
John F Kennedy Intl to Fort Myers flights
Islip to Orlando flights
Newark to Sarasota flights
Buffalo to Orlando flights
John F Kennedy Intl to Jacksonville flights
John F Kennedy Intl to Sarasota flights
LaGuardia to Jacksonville flights
White Plains to Tampa flights
LaGuardia to Sarasota flights
Stewart to Orlando flights
White Plains to Fort Lauderdale flights
Syracuse to Orlando flights
Newark to Key West flights
Stewart to Fort Lauderdale flights
Rochester to Orlando flights
Albany to Orlando flights
White Plains to Miami flights
Stewart to Tampa flights
John F Kennedy Intl to Daytona Beach flights
Newark to St Petersburg flights
Stewart to Fort Myers flights
LaGuardia to Pensacola flights
Islip to West Palm Beach flights
White Plains to West Palm Beach flights
John F Kennedy Intl to Key West flights
Newark to Pensacola flights
Buffalo to Fort Lauderdale flights
Stewart to West Palm Beach flights
Buffalo to Tampa flights
Newark to Orlando Sanford Intl flights
LaGuardia to Panama City flights

Top 4 airlines flying from Stewart to Orlando

Discover the top 4 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 May 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$55Average$207FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$81Average$171FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$127Average$229FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$167Average$244FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.