ORL - SWF

$54 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 2/13. 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, 0 bags

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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$137
Overall average: $162
Breeze Airways
Fri 2/6Mon 2/9
MCO - SWF • 1 stop
Cheapest non-stop
$161
Typical prices: $116-$325
Breeze Airways
Thu 5/21Sun 5/24
MCO - SWF • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Breeze's Nicer fare includes extra legroom and a free bag.
Allegiant's Legroom+ offers extra space for short flights.
Expert advice
Expert advice
Expert advice
Expert advice
Top routes
SFB
-
SWF
Cheapest • 7% average savings
SFB
-
SWF
Most popular
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 49% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
6 days a week
There are direct flights from Orlando to New Windsor 6 days a week: Mon, Wed, Thu, Fri, Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to New Windsor!
Flight Deals
Booking Insights
Expert advice
Flight 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

Fri, Feb 6 - Mon, Feb 9
Breeze Airways Logo
7:15 am - 11:31 am
MCO
-
SWF
4h 16m
1 stop
Breeze Airways Logo
12:11 pm - 4:49 pm
SWF
-
MCO
4h 38m
1 stop
$137Breeze Airways
Fri, Feb 6 - Mon, Feb 9
Breeze Airways Logo
7:15 am - 11:31 am
MCO
-
SWF
4h 16m
1 stop
Breeze Airways Logo
12:11 pm - 4:49 pm
SWF
-
MCO
4h 38m
1 stop
$138Breeze Airways
Thu, Mar 5 - Mon, Mar 9
Breeze Airways Logo
8:10 am - 11:08 am
MCO
-
SWF
2h 58mnonstop
Breeze Airways Logo
12:11 pm - 4:49 pm
SWF
-
MCO
4h 38m
1 stop
$150Breeze Airways
Fri, Feb 27 - Mon, Mar 2
Breeze Airways Logo
7:15 am - 11:31 am
MCO
-
SWF
4h 16m
1 stop
Breeze Airways Logo
12:11 pm - 4:49 pm
SWF
-
MCO
4h 38m
1 stop
$154Breeze Airways
Fri, Feb 27 - Mon, Mar 23
Breeze Airways Logo
7:15 am - 11:31 am
MCO
-
SWF
4h 16m
1 stop
Breeze Airways Logo
12:11 pm - 4:49 pm
SWF
-
MCO
4h 38m
1 stop
$157Breeze Airways
Thu, May 21 - Sun, May 24
Breeze Airways Logo
6:00 am - 8:58 am
MCO
-
SWF
2h 58mnonstop
Breeze Airways Logo
9:38 am - 12:44 pm
SWF
-
MCO
3h 06mnonstop
$161Breeze Airways
Fri, Mar 6 - Mon, Mar 9
Breeze Airways Logo
7:15 am - 11:31 am
MCO
-
SWF
4h 16m
1 stop
Breeze Airways Logo
12:11 pm - 4:49 pm
SWF
-
MCO
4h 38m
1 stop
$162Breeze Airways
Thu, Jun 18 - Tue, Jun 23
Breeze Airways Logo
6:00 am - 8:58 am
MCO
-
SWF
2h 58mnonstop
Breeze Airways Logo
11:48 am - 2:54 pm
SWF
-
MCO
3h 06mnonstop
$164Breeze Airways
Fri, Mar 20 - Sun, Mar 22
Breeze Airways Logo
7:15 am - 11:31 am
MCO
-
SWF
4h 16m
1 stop
Breeze Airways Logo
11:48 am - 3:07 pm
SWF
-
MCO
3h 19mnonstop
$165Breeze Airways
Fri, Feb 27 - Mon, Mar 2
Breeze Airways Logo
7:15 am - 11:31 am
MCO
-
SWF
4h 16m
1 stop
Breeze Airways Logo
12:11 pm - 4:49 pm
SWF
-
MCO
4h 38m
1 stop
$166Breeze Airways
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Orlando to New Windsor costs $88 on the route between Orlando Sanford Intl Airport (SFB) and New Windsor (SWF). Over the past month, this route was, on average, 7% cheaper than other Orlando-New Windsor routes. It is also the most popular route.

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 Tuesday 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 May, where tickets cost $104 (return) on average. On the other hand, the most expensive months are April and December, where the average cost of round-trip tickets is $286 and $265 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 $191, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Orlando to New Windsor

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Chris Dong

Chris Dong

Expert on Breeze Airways

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.

Daniel Scheffler

Daniel Scheffler

Expert on Allegiant Air

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.

Good to know

Low seasonMarch
Cheapest flight$58
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 14% lower on average.
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 $58 for a one-way ticket and $150 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 A321neo 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.

  • 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 $211 and an overall rating of 8.2, Breeze Airways is the most popular choice. Allegiant Air is also a great choice for the route, with an average price of $163 and an overall rating of 7.2.

  • 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 $115 or less one-way and $124 or less round-trip.

Prefer to fly direct from Orlando to Stewart Intl.?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Orlando to New Windsor Stewart.
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

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

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

Reviews of the 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.
8.2
Breeze AirwaysOverall score based on 263 reviews
8.3Boarding
6.6Entertainment
8.2Comfort
8.7Crew
6.7Food
Airline reviews

10 hour delay with minimal updates. Couldn’t leave terminal and then ended up on redeye with a dirty broken plane. It is literally impossible to reach customer service via gate agent, app, phone, text or email.

2.0 MediocreAnonymous, Jan 2026
PHX - BDL
Read more Breeze Airways reviews

10 hour delay with minimal updates. Couldn’t leave terminal and then ended up on redeye with a dirty broken plane. It is literally impossible to reach customer service via gate agent, app, phone, text or email.

I thought that I had pre-purchased carry-on luggage and was surprised when I tried to check in that I did not have it.

Flight departure was 90 min delayed, and the boarding experience was confused, stressful, and generally poor. Additionally, the wifi on the plane was malfunctioning for all but the final 15 min of the flight into ILM.

Great experience and In love flying in and out of Provo airport

You get what you pay for. It’s like a bus but flying. No frills, no snacks. Leg room was fine, boarding was good.

Overall good. Plenty of legroom and fairly comfortable seats. No issues with capacity and the overhead been even though most people brought several carry-ons on. I don’t think Breeze really enforces the pay for a carry-on rule.

Surprised at how much I enjoyed Breeze. Paid for the Nicer upgrade which made it closer in price to a flag ship carrier but with more comfortable seats and much more leg room. Crew was polite and since we brought our food no loss there. Would make the point that the ‘have to pay for a carry-on is BS’. Most people did not and had several. Still was plenty of room in the overheads.

Comfortable seating, adequate space available, nice to have USB port, polite crew.

My experience is typically great with Breeze. This trip wasn’t any different.

This was my first experience with Breeze. The plane was cleaner and more comfortable than any other I've experienced. The process of boarding was streamlined. We boarded early and arrived at our destination 45 minutes early. The only hiccup was my ticket was rejected by TSA PreCheck and I got sent to the back of a very long line at Fort Myers. I entered my information when I bought my ticket, but it apparently didn't connect to my permanent profile. I'll correct that for next time. I was expecting an Allegiant experience, but Breeze was much more upscale. I really, really enjoyed it.

It was fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

Clean, friendly, roomy. But check-in from the phone link was terrible. Repeated attempts wouldn’t save at the final step. Just kept spinning! It was very frustrating. Finally, I used the app (vs website link) to check-in which worked very smoothly on the first attempt.

Check in on the web portal was cumbersome! After several attempts I finally got the boarding pass.

Excellent flight and even arrived 23 min early. No entertainment , or wi fi on board, but I downloaded a couple of movies beforehand which kept me entertained. Really like flying Allegiant airlines.

WE were delayed about an hour and never any communications from the employees working the gate. We also were moved to a total of three gates.

I love how they show love to their customers and care about them too.

I liked how when I got on board how fast we ended up taking off but what I truly disliked was how uncomfortable the seats were. There was truly never a time that I could ever get comfortable during both of my flights. The seats could get away during shorter flights but flights 3 hour plus makes it hard to enjoy.

The crew was great and the flight was very smooth. Can’t really judge food since I did not get any because it costs money. The seat was comfortable for what we bought. Thanks!

Crew was great. No entertainment and food and beverage was for purchase only, even water

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

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

Information on your arrival and departure airports