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Stewart

$59+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SWF
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Orlando to New Windsor Stewart are usually found in February or May, booked 55 days in advance, depart on a Monday or Friday and return on a Saturday

Cheap 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 September 16, 2025.

Round-trip from

$136
(Orbitz)

One-way from

$61
(CheapOair)

Popular in

December

Cheapest in

February

Average price

$158
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. 19% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/218:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Sun 9/2811:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 9/14$140
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Sun 9/218:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 9/2912:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 9/14$150
This CheapOair deal was found by Cheapflights users on 9/15. 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.
Fri 12/57:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Mon 12/812:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 9/15$152
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 9/218:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Thu 9/2511:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 9/15$161
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 12/812:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 9/14$164
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 9/258:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Sun 9/2811:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 9/16$167
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Sun 10/2611:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 9/14$173
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Fri 12/57:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Sun 12/711:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 9/16$174

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 September 16, 2025.
Use the filters below to find and compare flights from Orlando Airport to New Windsor that are best for you.

Fly from

Orlando

Fly to

Stewart

Route

Depart

Return

Price

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 1/22

8:10 am-11:08 am

Nonstop2h 58m

New Windsor Stewart

Mon 1/26

12:11 pm-4:49 pm

1 stop4h 38m

$136

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 1/22

8:10 am-11:08 am

Nonstop2h 58m

New Windsor Stewart

Sun 1/25

11:48 am-3:07 pm

Nonstop3h 19m

$136

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 12/5

7:30 am-11:44 am

1 stop4h 14m

New Windsor Stewart

Mon 12/8

12:24 pm-4:59 pm

1 stop4h 35m

$152

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 1/16

7:15 am-11:31 am

1 stop4h 16m

New Windsor Stewart

Sun 1/18

11:48 am-3:07 pm

Nonstop3h 19m

$158

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 12/5

7:30 am-11:44 am

1 stop4h 14m

New Windsor Stewart

Sun 12/7

11:43 am-2:57 pm

Nonstop3h 14m

$174

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 9/26

7:30 am-11:44 am

1 stop4h 14m

New Windsor Stewart

Mon 9/29

12:24 pm-4:59 pm

1 stop4h 35m

$178

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 10/9

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Sun 10/12

11:43 am-2:57 pm

Nonstop3h 14m

$188

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 12/12

7:30 am-11:44 am

1 stop4h 14m

New Windsor Stewart

Mon 12/15

12:24 pm-4:59 pm

1 stop4h 35m

$192

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 10/30

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Mon 11/3

12:24 pm-4:59 pm

1 stop4h 35m

$199

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 11/14

7:30 am-11:44 am

1 stop4h 14m

New Windsor Stewart

Mon 11/17

12:24 pm-4:59 pm

1 stop4h 35m

$214

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 24 results
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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

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

Use this chart to determine the optimal time to book a round-trip flight from Orlando to Stewart. Price data was last updated on September 12, 2025.

The best time to book flights from Orlando Airport to New Windsor is 54 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 Orlando Airport to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Orlando Airport to New Windsor (average of $109). Flying from Orlando Airport to New Windsor in December is currently the most expensive (average of $202). 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 September 16, 2025.

When flying from Orlando Airport to New Windsor, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 33% versus a flight in the afternoon.

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 September 16, 2025.
Read through reviews of airlines operating flights from Orlando Airport to New Windsor, such as Breeze Airways and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
205 reviews

Boarding

8.2

Crew

8.7

Food

6.7

Comfort

8.1

Entertainment

6.5

Overall

8.0

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
205 reviews
Breeze Airways
8.0
Very good
205 reviews

Boarding

8.2

Crew

8.7

Food

6.7

Comfort

8.1

Entertainment

6.5

Overall

8.0

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Allegiant Air
7.2
Good
699 reviews
Breeze Airways
8.0
Very good
205 reviews

Boarding

8.2

Crew

8.7

Food

6.7

Comfort

8.1

Entertainment

6.5

Overall

8.0

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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. 2 airlines 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 $136, 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 are the cheapest airlines flying from Orlando Airport to New Windsor round-trip?

    Cheapflights users have booked flights from Orlando Airport to New Windsor round-trip from $74. Another airline that can offer you cheap pricing is Breeze Airways. Allegiant Air is priced at 59% 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 $153, our data shows the cheapest flight currently is $59. When looking at the most popular route, (Orlando - New Windsor Stewart), you can expect to pay $143 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, October is the cheapest month in which you can book a flight from Orlando Airport to New Windsor (average of $109). Flying from Orlando Airport to New Windsor in December is currently the most expensive (average of $202). 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 2 airlines flying from Orlando to Stewart

Discover the top 2 airlines 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$74Average$124FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$116Average$199FlexibilityNo cancel feeOn-timeN/A

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