ORL - SWF

$59 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 9/14. 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
1 adult, Economy

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 (ORL-SWF)

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Orlando to New Windsor

Thu, Sep 4 - Sun, Sep 7
Breeze Airways Logo
8:00 am - 10:53 amMCO-SWF
2h 53mnonstop
Breeze Airways Logo
11:33 am - 2:47 pmSWF-MCO
3h 14mnonstop
$122Breeze Airways
Find Deal
Thu, Sep 11 - Sun, Sep 14
Breeze Airways Logo
8:00 am - 10:53 amMCO-SWF
2h 53mnonstop
Breeze Airways Logo
11:33 am - 2:47 pmSWF-MCO
3h 14mnonstop
$127Breeze Airways
Find Deal
Fri, Sep 5 - Sun, Sep 7
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
$131Breeze Airways
Find Deal
Fri, Sep 12 - 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
$137Breeze Airways
Find Deal
Tue, Jul 1 - Sun, Aug 31
Breeze Airways Logo
9:00 am - 11:56 amMCO-SWF
2h 56mnonstop
Breeze Airways Logo
7:52 pm - 10:56 pmSWF-MCO
3h 04mnonstop
$142Breeze Airways
Find Deal
Thu, Aug 28 - Mon, Sep 1
Breeze Airways Logo
4:16 pm - 7:12 pmMCO-SWF
2h 56mnonstop
Breeze Airways Logo
1:28 pm - 5:55 pmSWF-MCO
4h 27m1 stop
$143Breeze Airways
Find Deal
Mon, Jul 14 - Thu, Aug 28
Breeze Airways Logo
8:30 am - 12:48 pmMCO-SWF
4h 18m1 stop
Breeze Airways Logo
7:52 pm - 10:56 pmSWF-MCO
3h 04mnonstop
$146Breeze Airways
Find Deal
Fri, Sep 5 - Mon, Sep 8
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
$147Breeze Airways
Find Deal
Fri, Aug 1 - Mon, Aug 4
 Logo
6:50 am - 7:06 pmMCO-SWF
12h 16m1 stop
 Logo
7:56 pm - 7:15 pmSWF-MCO
23h 19m1 stop
Thu, Jul 3 - Mon, Jul 7
 Logo
9:32 pm - 7:06 pmMCO-SWF
21h 34m1 stop
 Logo
7:56 pm - 7:18 amSWF-MCO
11h 22m1 stop
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 $39 and was between Orlando Sanford Intl Airport (SFB) and New Windsor (SWF). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $39.

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, Thursday 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 October, where the average cost of round-trip tickets is $323 and $223 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.

No, with an average price for the route of $139, prices are generally cheapest when you fly direct.

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 11 weeks before departure.

Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$59
Best time to beat the crowds with an average 52% drop in price.
Most popular time to fly with an average 3% 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.

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 $59 for a one-way ticket and $122 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 Tuesday, Wednesday, Thursday, Saturday, and Sunday.

  • Which is the best airline for flights from Orlando to New Windsor, Breeze Airways or Allegiant Air?

    The two airlines most popular with KAYAK users for flights from Orlando to New Windsor are Breeze Airways and Allegiant Air. With an average price for the route of $221 and an overall rating of 8.1, Breeze Airways is the most popular choice. Allegiant Air is also a great choice for the route, with an average price of $142 and an overall rating of 7.3.

  • 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 $89 or less one-way and $188 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, Breeze Airways

Allegiant Air, Breeze Airways

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, Breeze Airways

Allegiant Air, Breeze Airways

Sunday

Breeze Airways

Breeze Airways

See more direct flights
See more direct flights

Top airlines flying 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 178 reviews
6.7Food
8.2Comfort
6.6Entertainment
8.3Boarding
8.8Crew
Airline reviews

The flight was comfortable with the usual slight turbulence. Macadamia Nuts would be great snacks to purchase in flight.

10.0 ExcellentAnonymous, Jun 2025MCO - SBN
Read more Breeze Airways reviews

The flight was comfortable with the usual slight turbulence. Macadamia Nuts would be great snacks to purchase in flight.

This is one of the worst trips that I have ever had. Ending up with an overnight delay. I’m not happy with the fact that they did not provide and set up the arrangement needed for lodging that we had to do it on our own. I also feel there should’ve been Compensation for food.

Had to approach landing twice which caused concern but probably due to weather

This was my first time flying your airline and it was okay. The people were nice but I am not used to all the add ons and no movies or even water. But I knew it was going to be that way. I think I prefer paying for the extras to be more comfortable.

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.

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

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.

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

Information on your arrival and departure airports

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