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Stewart

$61+ Cheap flights from Orlando (ORL) 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — SWF
Sep 5 — Sep 121
Fri 9/5
Fri 9/12
1 adult, Economy
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Cheap flight deals from Orlando to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (ORL) 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 August 31, 2025.

Round-trip from

$125
(Priceline)

One-way from

$61
(Expedia)

Popular in

April

Cheapest in

January

Average price

$193
From Orlando (ORL) to New Windsor Stewart
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One-way flight from Orlando (ORL) to New Windsor Stewart
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Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 31, 2025.

This Priceline deal was found by Cheapflights users on 8/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/118:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Thu 9/1811:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 8/29$125
This Expedia deal was found by Cheapflights users on 8/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/118:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 9/1512:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 8/29$129
This Priceline deal was found by Cheapflights users on 8/30. 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 9/148:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Thu 9/1811:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 8/30$130
This Expedia deal was found by Cheapflights users on 8/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/148:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 9/1512:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 8/28$131
This CheapOair deal was found by Cheapflights users on 8/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/118:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 9/2212:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 8/29$132
This CheapOair deal was found by Cheapflights users on 8/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Sun 9/711:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 8/29$133
This CheapOair deal was found by Cheapflights users on 8/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Fri 9/1212:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 8/29$136
This CheapOair deal was found by Cheapflights users on 8/28. 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 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 8/28$139
This Priceline deal was found by Cheapflights users on 8/30. 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 9/288:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 9/2912:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 8/30$140
This Expedia deal was found by Cheapflights users on 8/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/188:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Sun 9/2111:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 8/29$142
This CheapOair deal was found by Cheapflights users on 8/30. 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 9/188:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 9/2912:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 8/30$145

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 August 31, 2025.
Use the filters below to find and compare flights from Orlando 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 9/11

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Thu 9/18

11:43 am-2:57 pm

Nonstop3h 14m

$125

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 1/8

8:10 am-11:08 am

Nonstop2h 58m

New Windsor Stewart

Sun 1/11

11:48 am-3:07 pm

Nonstop3h 19m

$127

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 9/11

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Mon 9/15

12:24 pm-4:59 pm

1 stop4h 35m

$129

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Sun 9/14

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Thu 9/18

11:43 am-2:57 pm

Nonstop3h 14m

$130

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Sun 9/14

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Mon 9/15

12:24 pm-4:59 pm

1 stop4h 35m

$131

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Mon 9/15

7:30 am-11:44 am

Nonstop4h 14m

New Windsor Stewart

Thu 9/18

11:43 am-2:57 pm

Nonstop3h 14m

$132

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 9/11

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Mon 9/22

12:24 pm-4:59 pm

1 stop4h 35m

$132

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

$132

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 1/22

8:10 am-11:08 am

Nonstop2h 58m

$61

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Sun 9/21

8:10 am-11:03 am

Nonstop2h 53m

$61

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/28

Showing 1-10 of 14 results
1
2

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 to New Windsor

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

Currently, October is the cheapest month in which you can book a flight from Orlando to New Windsor (average of $109). Flying from Orlando 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 ORL 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 August 31, 2025.

It’s typically best to fly out from Orlando to New Windsor in the afternoon. Doing so could potentially save you 8% on the flight price compared to flying in the morning, which is usually more expensive.

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

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 August 31, 2025.
Get a feel of what it's like to fly with Breeze Airways and Allegiant Air from Orlando to New Windsor by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
200 reviews

Crew

8.7

Boarding

8.2

Food

6.7

Entertainment

6.6

Comfort

8.1

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
200 reviews
Breeze Airways
8.0
Very good
200 reviews

Crew

8.7

Boarding

8.2

Food

6.7

Entertainment

6.6

Comfort

8.1

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
703 reviews
Breeze Airways
8.0
Very good
200 reviews

Crew

8.7

Boarding

8.2

Food

6.7

Entertainment

6.6

Comfort

8.1

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?

    For a flight from Orlando to New Windsor, you will be flying into Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city. Stewart is the only New Windsor airport and it handles 0 inbound flights from Orlando per day. 2 airlines have flights to New Windsor Stewart from Orlando on a regular basis.

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

    Breeze Airways can get you from Orlando to New Windsor in just under 2h 53m. Your travel time will be generally consistent. The distance from Orlando to New Windsor is about 989 mi. Most flights are nonstop.

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

    Currently priced at $74, Allegiant Air will fly you from Orlando to New Windsor and back. In addition to Allegiant Air, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Breeze Airways for as low as $116. Allegiant Air is currently priced 59% below the average price you’ll pay for this route.

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

    Looking for the cheapest flight from Orlando to New Windsor? While on average our users pay $153, our data indicates the cheapest price to be $59. The most popular route (Orlando - New Windsor Stewart), is priced around $125.

  • 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 to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Orlando to New Windsor (average of $109). Flying from Orlando 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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Alternative routes for Orlando to Stewart

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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 August 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$74Average$132FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$116Average$202FlexibilityNo cancel feeOn-timeN/A

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