ORL - SWF

$60 Find Cheap Flights from Orlando to New Windsor

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Orlando to New Windsor departing on 5/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to New Windsor

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Orlando to New Windsor, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Orlando to New Windsor, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Orlando to New Windsor

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Orlando to New Windsor that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Orlando to New Windsor

KAYAK's recommended round-trip deals from the most popular airlines that fly from Orlando to New Windsor.
Discover the best prices for you by selecting your travel dates on KAYAK.
Breeze Airways Logo
8:00 am - 10:53 amMCO-SWF
2h 53mnonstop
Breeze Airways Logo
11:33 am - 2:47 pmSWF-MCO
3h 14mnonstop
$119Breeze Airways
Find Deal
Thu, Sep 11 - Sun, Sep 14
Breeze Airways Logo
7:30 am - 11:44 amMCO-SWF
4h 14m1 stop
Breeze Airways Logo
11:33 am - 2:47 pmSWF-MCO
3h 14mnonstop
$122Breeze Airways
Find Deal
Fri, Sep 12 - Sun, Sep 14
Breeze Airways Logo
8:00 am - 10:53 amMCO-SWF
2h 53mnonstop
Breeze Airways Logo
12:24 pm - 4:59 pmSWF-MCO
4h 35m1 stop
$124Breeze Airways
Find Deal
Thu, Sep 4 - Mon, Sep 15
Breeze Airways Logo
8:00 am - 10:53 amMCO-SWF
2h 53mnonstop
Breeze Airways Logo
11:33 am - 2:47 pmSWF-MCO
3h 14mnonstop
$126Breeze Airways
Find Deal
Thu, Sep 18 - Sun, Sep 28
Breeze Airways Logo
7:30 am - 11:44 amMCO-SWF
4h 14m1 stop
Breeze Airways Logo
12:24 pm - 4:59 pmSWF-MCO
4h 35m1 stop
$127Breeze Airways
Find Deal
Fri, Sep 12 - Mon, Sep 15
Breeze Airways Logo
8:30 am - 11:26 amMCO-SWF
2h 56mnonstop
Breeze Airways Logo
12:06 pm - 3:10 pmSWF-MCO
3h 04mnonstop
$129Breeze Airways
Find Deal
Thu, May 22 - Sun, May 25
Breeze Airways Logo
8:30 am - 11:26 amMCO-SWF
2h 56mnonstop
Breeze Airways Logo
12:06 pm - 3:10 pmSWF-MCO
3h 04mnonstop
$132Breeze Airways
Find Deal
Thu, May 22 - Sun, May 25
Breeze Airways Logo
8:30 am - 11:26 amMCO-SWF
2h 56mnonstop
Breeze Airways Logo
12:06 pm - 3:10 pmSWF-MCO
3h 04mnonstop
$134Breeze Airways
Find Deal
Thu, May 22 - Sun, May 25
 Logo
8:17 am - 11:05 amMCO-SWF
26h 48m1 stop
 Logo
11:55 am - 7:07 amSWF-MCO
19h 12m1 stop
Thu, May 22 - Mon, May 26
 Logo
7:40 pm - 7:06 pmMCO-SWF
23h 26m1 stop
 Logo
7:56 pm - 11:00 pmSWF-MCO
27h 04m1 stop
Thu, Jul 24 - Mon, Jul 28
Expert advice

Expert advice for your flight from Orlando to New Windsor

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Breeze Airways

Breeze's Nicer fare includes extra legroom, priority check-in, and a free checked bag.


Breeze offers free Wi-Fi on Airbus A220 for Nicer and Nicest fares, enhancing onboard experience.

Allegiant Air

Allegiant's Legroom+ offers extra space and faster deplaning, ideal for short flights.


Allegiant's Trip Flex allows one free flight change or cancellation, enhancing travel flexibility.

Our travel experts
Chris Dong

Chris Dong

Expert on Breeze Airways

Chris Dong

Chris Dong

Chris is a consumer travel reporter covering aviation, trending travel news, hotels, and loyalty programs—all for leading global publications like Travel + Leisure, The Washington Post, AFAR, and more. In addition to writing, Chris is a video host for Travel + Leisure, giving consumers an inside look at the latest in air travel.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Allegiant Air

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Useful Info

KAYAK's insights & trends for Orlando to New Windsor flights

Get data-powered insights and trends into flights from Orlando to New Windsor to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Orlando to New Windsor flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Orlando to New Windsor.

Our data shows that the cheapest route for a return flight from Orlando to New Windsor cost $73 and was between Orlando Airport (MCO) and New Windsor (SWF). On average, the best prices are found if you fly from Orlando Sanford Intl Airport (SFB) to New Windsor (SWF). The average price for a return flight for this route is $73.

What’s the cheapest day of the week to fly from Orlando to Stewart Intl.?

The average price of all round-trip flights from Orlando to New Windsor clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Stewart Intl. on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Orlando to Stewart Intl.. For your return ticket, we recommend flying on a Wednesday and avoiding Mondays for the best deals.

What is the cheapest month to fly from Orlando to New Windsor?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Orlando to New Windsor, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Orlando to New Windsor is January, where tickets cost $88 (return) on average. On the other hand, the most expensive months are April and August, where the average cost of round-trip tickets is $349 and $214 respectively.

Can I save money by flying with a layover from Orlando to New Windsor?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $118 on average.

How far in advance should I book a flight from Orlando to New Windsor?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Orlando to New Windsor, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Orlando to New Windsor, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$60
Best time to beat the crowds with an average 54% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Orlando Airport to Stewart Intl.

When to book flights from Orlando to New Windsor

Are your dates flexible? Find out the best times to travel from Orlando to New Windsor based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

Flights from Orlando to New Windsor: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Orlando to New Windsor 
LoriFlew with Allegiant AirSFB-SWFMar 2025
No off site parking so the cheapest lot is $15 a day which is pretty steep for me. I won’t book a flight through there again unless I don’t have to leave my car.
HenryFlew with Breeze AirwaysMCO-SWFAug 2024
For MCO arrive with plenty of time to make it through the TSA checkpoint. Stewart / Newburgh is a great smaller airport to fly in or out of.

FAQs for booking flights from Orlando to Stewart Intl.

  • What is the cheapest flight from Orlando to New Windsor?

    In the last 3 days, the lowest price for a flight from Orlando to New Windsor was $60 for a one-way ticket and $119 for a round-trip.

  • Do I need a passport to fly between Orlando and Stewart Intl.?

    Yes, you’ll need a passport to travel to Stewart Intl. from Orlando.

  • Which airports will I be using when flying from Orlando to Stewart Intl.?

    On your way to Stewart Intl., you’ll fly out from one of these Orlando airports: Orlando or Orlando Sanford Intl. You’ll be landing at New Windsor Stewart.

  • Which airlines offer Wi-Fi service onboard planes from Orlando to Stewart Intl.?

    JetBlue, Delta, and American Airlines offer inflight Wi-Fi service on the Orlando to Stewart Intl. flight route.

  • Which aircraft models fly most regularly from Orlando to Stewart Intl.?

    The Airbus A320neo is the aircraft model that flies most regularly on the Orlando to Stewart Intl. flight route.

  • On which days can I fly direct from Orlando to Stewart Intl.?

    You can catch a nonstop flight from Orlando to Stewart Intl. on on Monday, Wednesday, Thursday, Friday, Saturday, and Sunday.

  • How does KAYAK find such low prices on flights from Orlando to Stewart Intl.?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Orlando to Stewart Intl..

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Orlando to Stewart Intl.?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Stewart Intl. from Orlando is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Orlando to Stewart Intl.?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Stewart Intl. with an airline and back to Orlando with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Orlando to Stewart Intl.?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Stewart Intl. from Orlando up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Orlando to New Windsor

  • Looking for a cheap flight? 25% of our users found flights on this route for $96 or less one-way and $141 or less round-trip.

Prefer to fly direct from Orlando to Stewart Intl.?

Find which airlines fly direct from Orlando to New Windsor Stewart Airport, which days they fly and book direct flights.

Direct departures

Orlando to New Windsor Stewart

Monday

Allegiant Air

Allegiant Air

Tuesday

Breeze Airways

Breeze Airways

Wednesday

Allegiant Air

Allegiant Air

Thursday

Breeze Airways

Breeze Airways

Friday

Allegiant Air

Allegiant Air

Saturday

Allegiant Air

Allegiant Air

Sunday

Breeze Airways

Breeze Airways

See more direct flights

Direct returns

New Windsor Stewart to Orlando

Monday

Allegiant Air

Allegiant Air

Tuesday

Breeze Airways

Breeze Airways

Wednesday

Allegiant Air

Allegiant Air

Thursday

Breeze Airways

Breeze Airways

Friday

Allegiant Air

Allegiant Air

Saturday

Allegiant Air

Allegiant Air

Sunday

Breeze Airways

Breeze Airways

See more direct flights
See more direct flights

Top 3 airlines serving from Orlando to New Windsor

 
See real verified KAYAK customer reviews for airlines flying from Orlando to New Windsor. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Orlando to New Windsor? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
Breeze AirwaysOverall score based on 160 reviews
6.6Entertainment
8.8Crew
8.3Boarding
8.2Comfort
6.7Food
Airline reviews

Plane did no snacks and had no wifi or entertainment although the flight was 4 hours long.

8.0 ExcellentAnonymous, Apr 2025PVU - IAD
Read more Breeze Airways reviews

Plane did no snacks and had no wifi or entertainment although the flight was 4 hours long.

My original booking was a nonstop flight. It got changed to a flight with a 6vhour layover that became a 7+ hour lay over. I'll never fly this airline again after this roundtrip is over.

I was surprised at how wonderful it was. The aircraft was clean. The crew was warm and welcoming and as a result the passengers were friendly. One warning the only free thing was water. I kind of liked picking wet hat I was willing to pay for and what I was willing to skip.

The flight wasn’t big on frills, which is fine with me. I flew into Islip MacArthur Airport, which saved me from having to go through LaGuardia to visit friends on Long Island. It was inexpensive and super convenient!

Great experience! This was my first time flying with them and I could not have been happier.

Airplane was newer and very clean, lots of space. Crew was great. There was no food and entertainment but that was expected so not an issue.

I like that the price is right! The airplane is clean and the staff is friendly. We landed safely, so that is always a gold star in my book! Great job!

Purposely delayed the flight by 2 hours and 58 minutes so that they would not have to give me the FAA mandated refund for a delay of 3 hours. Offered flight credit instead. All that is offered on board is water and coffee, everything else costs money. They charge you for carry on and checked bags. Would not fly again.

nice flight. no frills but a 3 hour flight I caught up on my sleep. Stan O

First time flying Breeze, was very impressed. I will use Breeze again.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

Posted a 20minute delay but didn’t delay at all. Caused boarding issues and confusion. Also, didn’t release baggage. Took over an hour and 20 minutes to get luggage.

Flight was good, boarding was a breeze, flight attendants were friendly and professional. There was a medical issue with another passenger and the crew handled it in a calm and professional way.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

I paid for streaming wifi and the connection was poor.

Very efficient process and boarding, seats felt standard. Flight conditions from take off to landing had been very smooth. Alcohol on the menu however was not available… Will fly Spirit in the future for the price, you can’t really complain if you fly light.

Bad experience. Unhappy with the changing of flight times and one particular flight attendant (Bartholomew) on our flight from Orlando to Detroit. Traveling with a large family of 7, including our 18 month old, can be arduous but when the airline changes your flight time from landing at 9:30 pm to landing after midnight, this becomes much more difficult. When our 18 month old was predictably over tired and fussy, my wife and I tried to move to an open row so we can console her more effectively. The flight attendent rebuked us and said we could not sit in an exit row. We were not planning on sitting there for more than a few minutes but just to have space to console our screaming 18 month old. Spirit did not allow for a family friendly trip. Likely will be choosing a different airline next time.

This was my first experience with Spirit. The flight was originally delayed because of mechanical problems. There was a major storm moving through our area later in the day. Spirit kept changing the gate and taking the plane for other flights. They did this 6 times until we left 7 hours later, right at the worse time. I am sure it is because they originally delayed the flight through their fault. They would have had to pay for everybody's hotel and later flight. It was a money decision. The pilot did an exceptional job flying and landing the plane in horrific weather. It was one of the roughest and shakiest landings that I have ever done in my extensive flying experience. I just can never go through this discount BS again. Spirit gave us a $30 voucher each for next travel and a $12 meal voucher... but that's nothing compared to sitting in an airport for 7 hours.

Everything on the flight was OK. However, the price is very deceiving the way that it is marketed. It seems like it’s going to be very low cost, but when you add in the charges for luggage, choosing a seat, food & drink, etc., that are already included in other competitors fares, it really is no cheaper, and possibly even more expensive than the other carriers. It actually makes your carrier seem dishonest.

The reservation was cancelled after a day and a half due to family reasons. There was no flight from Newark to Orlando 03.01.2025. Very bad customer service. Never use again.

Overall good experience for the price. Thank you for making travel affordable.

The seats were comfortable and not as tight as i would have expected. Would have been nice to be able to recline my seat, which was not available. Some form of free snacks and drink option would be appreciated as well, even just a water and small bag of crackers would have been better than nothing at all.

Bad seats. Very uncomfortable. Crew was fine. Too much upcsharging

Everything you need to know for your flight from Orlando to New Windsor

Information on your arrival and departure airports

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