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Stewart

$43+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — SWF
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap 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 December 8, 2025.

This Super.com deal was found by Cheapflights users on 12/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 1/2612:11 pmSWF - MCO
Nonstop4h 38mBreeze Airways
Deal found 12/7$128
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/256:45 amMCO - SWF
1 stop28h 22mMultiple Airlines
Mon 1/2612:11 pmSWF - MCO
1 stop4h 38mMultiple Airlines
Deal found 12/7$152
This CheapOair deal was found by Cheapflights users on 12/6. 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 12/258:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Thu 1/111:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 12/6$178
This CheapOair deal was found by Cheapflights users on 12/6. 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 12/258:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Fri 1/912:11 pmSWF - MCO
1 stop4h 38mBreeze Airways
Deal found 12/6$181
This Expedia deal was found by Cheapflights users on 12/7. 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.
Tue 12/308:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Thu 1/111:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 12/7$183
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/127:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Sun 12/1411:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 12/6$189
This CheapOair deal was found by Cheapflights users on 12/6. 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 12/267:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Thu 1/111:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 12/6$191
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/118:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Sun 12/1411:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 12/6$198

Find 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 December 8, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$108
(Expedia)

One-way from

$43
(Expedia)

Popular in

April

Cheapest in

January

Average price

$179
Provider with most accurate pricing for Orlando (ORL)-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-New Windsor Stewart flights.
Search Deals
From Orlando (ORL) to New Windsor Stewart
Search Deals
One-way flight from Orlando (ORL) to New Windsor Stewart
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 8, 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

Fri 1/30

7:15 am-11:31 am

1 stop4h 16m

New Windsor Stewart

Sun 2/1

12:13 pm-3:32 pm

Nonstop3h 19m

$115

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 1/29

8:35 am-11:33 am

Nonstop2h 58m

New Windsor Stewart

Mon 2/2

12:11 pm-4:49 pm

1 stop4h 38m

$116

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 1/22

8:35 am-11:33 am

Nonstop2h 58m

New Windsor Stewart

Sun 1/25

12:13 pm-3:32 pm

Nonstop3h 19m

$122

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 2/6

7:15 am-11:31 am

1 stop4h 16m

New Windsor Stewart

Sun 2/8

11:48 am-3:07 pm

Nonstop3h 19m

$122

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 1/15

8:35 am-11:33 am

Nonstop2h 58m

New Windsor Stewart

Sun 1/18

12:13 pm-3:32 pm

Nonstop3h 19m

$122

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 1/8

8:35 am-11:33 am

Nonstop2h 58m

New Windsor Stewart

Mon 1/12

12:11 pm-4:49 pm

1 stop4h 38m

$123

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 12/25

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Mon 1/26

12:11 pm-4:49 pm

Nonstop4h 38m

$128

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 1/23

7:15 am-11:31 am

1 stop4h 16m

New Windsor Stewart

Sun 1/25

12:13 pm-3:32 pm

Nonstop3h 19m

$130

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Mon 2/9

7:15 am-11:31 am

1 stop4h 16m

$43

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 1/30

7:15 am-11:31 am

1 stop4h 16m

$53

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 16 results
1
2

Compare providers for flights from Orlando to Stewart

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 Orlando to Stewart in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 Orlando-New Windsor flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Orlando-New Windsor flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Orlando-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando-New Windsor flights, Cheapflights users trust eDreams the most. eDreams 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 Orlando-New Windsor 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 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, February is the cheapest month in which you can book a flight from Orlando to New Windsor (average of $46). Flying from Orlando to New Windsor in July is currently the most expensive (average of $82). 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 December 8, 2025.

It’s typically best to fly out from Orlando to New Windsor in the evening. Doing so could potentially save you 16% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 December 8, 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
8.2
Very good
242 reviews

Entertainment

6.6

Overall

8.2

Food

6.7

Comfort

8.2

Boarding

8.4

Crew

8.8

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Breeze Airways
8.2
Very good
242 reviews
Breeze Airways
8.2
Very good
242 reviews

Entertainment

6.6

Overall

8.2

Food

6.7

Comfort

8.2

Boarding

8.4

Crew

8.8

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Allegiant Air
7.2
Good
698 reviews
Breeze Airways
8.2
Very good
242 reviews

Entertainment

6.6

Overall

8.2

Food

6.7

Comfort

8.2

Boarding

8.4

Crew

8.8

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

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 4h 16m. Your travel time can differ by up to . The distance from Orlando to New Windsor is about 989 mi.

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

    Currently priced at $76, 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 58% 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 $185, our data indicates the cheapest price to be $59. The most popular route (Orlando - New Windsor Stewart), is priced around $118.

  • 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, February is the cheapest month in which you can book a flight from Orlando to New Windsor (average of $46). Flying from Orlando to New Windsor in July is currently the most expensive (average of $82). 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 December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$76Average$139FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$118Average$196FlexibilityNo cancel feeOn-timeN/A

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