HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — SWF
Nov 12 — Nov 191
Wed 11/12
Wed 11/19
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Orlando to Stewart 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.

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 October 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$130
(CheapOair)

One-way from

$61
(CheapOair)

Popular in

April

Cheapest in

January

Average price

$303
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 October 2025
Search Deals

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 October 13, 2025.

This Expedia deal was found by Cheapflights users on 10/12. 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 12/48:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 12/812:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 10/12$130
This CheapOair deal was found by Cheapflights users on 10/13. 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 10/13$141
This CheapOair deal was found by Cheapflights users on 10/11. 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 12/78:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Thu 12/1111:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 10/11$147
This CheapOair deal was found by Cheapflights users on 10/13. 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 12/48:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Sun 12/711:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 10/13$152
This Orbitz deal was found by Cheapflights users on 10/11. 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 12/127:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Sun 12/1411:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 10/11$153
This CheapOair deal was found by Cheapflights users on 10/12. 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 10/317:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Mon 11/1012:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 10/12$154
This CheapOair deal was found by Cheapflights users on 10/11. 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 11/68:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 11/1012:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 10/11$158
This CheapOair deal was found by Cheapflights users on 10/13. 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 11/77:30 amMCO - SWF
1 stop4h 14mBreeze Airways
Mon 11/1012:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 10/13$159
This Priceline deal was found by Cheapflights users on 10/12. 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 12/148:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Mon 12/1512:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Deal found 10/12$160
This CheapOair deal was found by Cheapflights users on 10/11. 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 11/68:10 amMCO - SWF
Nonstop2h 53mBreeze Airways
Thu 11/1311:43 amSWF - MCO
Nonstop3h 14mBreeze Airways
Deal found 10/11$162

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 October 13, 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 2/5

8:10 am-11:08 am

Nonstop2h 58m

New Windsor Stewart

Sun 2/8

11:48 am-3:07 pm

Nonstop3h 19m

$128

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 12/4

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Mon 12/8

12:24 pm-4:59 pm

1 stop4h 35m

$130

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 1/29

8:10 am-11:08 am

Nonstop2h 58m

New Windsor Stewart

Mon 2/2

12:11 pm-4:49 pm

1 stop4h 38m

$132

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 12/12

7:30 am-11:44 am

1 stop4h 14m

New Windsor Stewart

Sun 12/14

11:43 am-2:57 pm

Nonstop3h 14m

$134

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

$141

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Sun 12/7

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Thu 12/11

11:43 am-2:57 pm

Nonstop3h 14m

$147

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 12/4

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Sun 12/7

11:43 am-2:57 pm

Nonstop3h 14m

$152

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 10/31

7:30 am-11:44 am

1 stop4h 14m

New Windsor Stewart

Mon 11/10

12:24 pm-4:59 pm

1 stop4h 35m

$154

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Thu 11/6

8:10 am-11:03 am

Nonstop2h 53m

New Windsor Stewart

Mon 11/10

12:24 pm-4:59 pm

1 stop4h 35m

$154

OrlandoNew Windsor

MCO - SWF

MCOSWF

Orlando

Fri 11/7

7:30 am-11:44 am

1 stop4h 14m

New Windsor Stewart

Mon 11/10

12:24 pm-4:59 pm

1 stop4h 35m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/10

Showing 1-10 of 17 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando-New Windsor flight deals on Cheapflights vs. FlightHub >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 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 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 $85). 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 October 13, 2025.

It’s typically best to fly out from Orlando to New Windsor in the evening. Doing so could potentially save you 17% 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 October 13, 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
8.1
Very good
217 reviews

Food

6.7

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

6.6

Comfort

8.2

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
8.1
Very good
217 reviews
Breeze Airways
8.1
Very good
217 reviews

Food

6.7

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

6.6

Comfort

8.2

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
694 reviews
Breeze Airways
8.1
Very good
217 reviews

Food

6.7

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

6.6

Comfort

8.2

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 58m. 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 $232, our data indicates the cheapest price to be $84. The most popular route (Orlando - New Windsor Stewart), is priced around $128.

  • 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 $85). 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

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 Orlando to Stewart

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

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 October 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$74Average$130FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$116Average$198FlexibilityNo cancel feeOn-timeN/A

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.