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$51+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORL
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from New Windsor Stewart to Orlando are usually found in March or May, booked 34 days in advance, depart on a Friday or Monday 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 January 29, 2026.

This Mytrip deal was found by Cheapflights users on 1/28. 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 3/2312:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Fri 3/277:15 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 1/28$130
This Kiwi.com deal was found by Cheapflights users on 1/26. 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
Fri 9/117:15 am
MCO
-
SWF
1 stop4h 20m
Breeze Airways
Deal found 1/26$133
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 58m
Breeze Airways
Deal found 1/26$136
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/912:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Fri 2/137:15 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 1/27$140
This Orbitz deal was found by Cheapflights users on 1/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:15 pm
SWF
-
MCO
1 stop4h 34m
Breeze Airways
Sun 9/136:00 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Deal found 1/28$142
This Mytrip deal was found by Cheapflights users on 1/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Fri 2/277:15 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 1/27$145
This Mytrip deal was found by Cheapflights users on 1/28. 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 3/212:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Fri 3/67:15 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 1/28$147
This Kiwi.com deal was found by Cheapflights users on 1/26. 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
Sat 9/127:00 am
MCO
-
SWF
1 stop4h 25m
Breeze Airways
Deal found 1/26$148
This Mytrip deal was found by Cheapflights users on 1/29. 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 3/1511:48 am
SWF
-
MCO
Nonstop3h 19m
Breeze Airways
Fri 3/207:15 am
MCO
-
SWF
1 stop4h 16m
Breeze Airways
Deal found 1/29$151
This Mytrip deal was found by Cheapflights users on 1/28. 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 3/2211:48 am
SWF
-
MCO
Nonstop3h 19m
Breeze Airways
Thu 3/268:10 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Deal found 1/28$152
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/912:11 pm
SWF
-
MCO
1 stop4h 38m
Breeze Airways
Thu 2/128:10 am
MCO
-
SWF
Nonstop2h 58m
Breeze Airways
Deal found 1/27$153

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$130
(Mytrip)

One-way from

$51
(Mytrip)

Popular in

November

Cheapest in

March

Average price

$147
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. 19% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
Use the filters below to find and compare flights from New Windsor to Orlando that are best for you.

Fly from

Stewart

Fly to

Orlando

Route

Depart

Return

Price

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 2/9

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Fri 2/13

7:15 am-11:31 am

1 stop4h 16m

$154

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 3/16

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Fri 3/20

7:15 am-11:31 am

1 stop4h 16m

$157

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 2/8

11:48 am-3:07 pm

Nonstop3h 19m

Orlando

Thu 2/12

8:10 am-11:08 am

Nonstop2h 58m

$158

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 2/22

11:48 am-3:07 pm

Nonstop3h 19m

Orlando

Fri 2/27

7:15 am-11:31 am

1 stop4h 16m

$166

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Sun 3/15

11:48 am-3:07 pm

Nonstop3h 19m

Orlando

Thu 3/26

8:10 am-11:08 am

Nonstop2h 58m

$168

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Thu 2/26

11:48 am-3:07 pm

Nonstop3h 19m

Orlando

Thu 3/5

8:10 am-11:08 am

Nonstop2h 58m

$168

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 2/9

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Sun 2/15

8:10 am-11:08 am

Nonstop2h 58m

$170

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 2/2

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Thu 2/5

8:10 am-11:08 am

Nonstop2h 58m

$175

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 2/2

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Sun 2/8

8:10 am-11:08 am

Nonstop2h 58m

$183

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 3/23

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Mon 3/30

7:15 am-11:31 am

1 stop4h 16m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 19 results
1
2

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 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?

Use this chart to determine the optimal time to book a round-trip flight from Stewart to Orlando. Price data was last updated on January 23, 2026.

The best time to book flights from New Windsor to Orlando is 34 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 August is currently the most expensive (average of $91). 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 January 29, 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 morning.

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 January 29, 2026.
Read through reviews of airlines operating flights from New Windsor to Orlando, such as Breeze Airways, JetBlue, and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
JetBlue
7.2
Good
2,891 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Allegiant Air
7.2
Good
706 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Spirit Airlines
6.3
Okay
8,394 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Frontier
5.7
Fair
3,056 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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. 5 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 4h 38m. Breeze Airways provides one of the quickest options available for as low as $154. 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 Frontier is currently your cheapest option to Orlando, with prices starting at $40. Additional round-trip tickets that might be worth considering are offered by Spirit Airlines and Allegiant Air, with the lowest prices starting at $55 and $80, respectively. Users have found that Frontier is 80% 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 $54. While the most popular route (New Windsor Stewart - Orlando) can be booked for $152 on average, our data indicates $206 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 August is currently the most expensive (average of $91). 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

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Alternative routes for Stewart to Orlando

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Stewart to Orlando

Discover the top 5 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$40Average$52FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$55Average$218FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$80Average$130FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$123Average$233FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$167Average$249FlexibilityNo cancel feeOn-time62%

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