ORL - SWF

$58 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 9/3. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$132
Overall average: $153
Breeze Airways
Thu 9/3Sun 9/6
MCO - SWF • Non-stop
Cheapest non-stop
$155
Typical prices: $133-$325
Breeze Airways
Thu 5/21Sun 5/31
MCO - SWF • Non-stop
Advice from real travelers
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
Nonstop flights
Mon, Thu, Fri, Sat, Sun
You can fly direct with Allegiant Air and Breeze Airways. Average duration is 2h 43m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 5% average savings
Most popular
Insights
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Insights
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

Thu, Sep 3 - Sun, Sep 6
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
$132Breeze Airways
Sat, May 30 - Mon, Jun 1
Breeze Airways Logo
7:00 am - 11:25 am
MCO
-
SWF
4h 25m
1 stop
Breeze Airways Logo
12:15 pm - 4:49 pm
SWF
-
MCO
4h 34m
1 stop
$136Breeze Airways
Fri, Apr 24 - Mon, Apr 27
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
Thu, May 7 - Mon, May 11
Breeze Airways Logo
6:00 am - 8:58 am
MCO
-
SWF
2h 58mnonstop
Breeze Airways Logo
12:15 pm - 4:49 pm
SWF
-
MCO
4h 34m
1 stop
$141Breeze Airways
Fri, Apr 24 - Mon, Apr 27
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
$143Breeze Airways
Wed, Sep 9 - Sat, Sep 12
Breeze Airways Logo
7:00 am - 11:25 am
MCO
-
SWF
4h 25m
1 stop
Breeze Airways Logo
12:05 pm - 5:02 pm
SWF
-
MCO
4h 57m
1 stop
$144Breeze Airways
Wed, Sep 9 - Fri, Sep 11
Breeze Airways Logo
7:00 am - 11:25 am
MCO
-
SWF
4h 25m
1 stop
Breeze Airways Logo
12:15 pm - 4:49 pm
SWF
-
MCO
4h 34m
1 stop
$145Breeze Airways
Fri, Apr 24 - Sun, Apr 26
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
$146Breeze Airways
Thu, May 7 - Mon, May 11
Breeze Airways Logo
6:00 am - 8:58 am
MCO
-
SWF
2h 58mnonstop
Breeze Airways Logo
12:15 pm - 4:49 pm
SWF
-
MCO
4h 34m
1 stop
$147Breeze Airways
Thu, May 7 - Sat, May 9
Breeze Airways Logo
6:00 am - 8:58 am
MCO
-
SWF
2h 58mnonstop
Breeze Airways Logo
12:05 pm - 11:59 pm
SWF
-
MCO
11h 54m
1 stop
$148Breeze 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 $79 on the route between Orlando Airport (MCO) and New Windsor (SWF). Over the past month, this route was, on average, 5% cheaper than other Orlando-New Windsor routes. The most popular route is between Orlando Sanford Intl Airport (SFB) and New Windsor (SWF).

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 Friday, 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 Fridays for the best deals.

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 $166, 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 seasonMay
Cheapest flight$58
Best time to beat the crowds with an average 50% drop in price.
Most popular time to fly and prices are also 15% 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 $132 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, 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 $223 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 $163 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 $141 or less one-way and $158 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

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

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.
8.1
Breeze AirwaysOverall score based on 271 reviews
6.6Entertainment
8.7Crew
6.6Food
8.3Boarding
8.2Comfort
Airline reviews

Our flight was delayed 7 hours. Due to a change in equipment we were downgraded from "Nicest" to "Nicer," even having to pay for a soft drink. Disappointing. To Breeze's credit that issued a $100 flight credit. A refund would have been more appreciated.

6.0 GoodJames, Feb 2026
RDU - RSW
Read more Breeze Airways reviews

Our flight was delayed 7 hours. Due to a change in equipment we were downgraded from "Nicest" to "Nicer," even having to pay for a soft drink. Disappointing. To Breeze's credit that issued a $100 flight credit. A refund would have been more appreciated.

Lost my luggage and terrible experience with customer service trying to track it down

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.

Superb. Staff great. Great flight. As with other airlines, seating too tight and restrictive.

There is not one likable thing about this airline. It’s starts with the deceptive pricing and continues through the whole flight. The worst staff I’ve ever experienced way over priced bags absolutely no food or drink (unacceptable and you should be embarrassed) the seats are cramped and uncomfortable there is no entertainment there is nothing about this trash airline that constitutes any amount of money. It’s worse than spirit and way more expensive it is disgraceful. Do not travel with Allegiant I repeat do not bother no matter what they say the price is it is never ever going to be the right choice I’m mind blown at how awful the entire experience was I’m embarrassed that I chose so poorly I cannot reiterate enough how beyond horrible this company and its staff are, not one person on this flight or at the airport is qualified to sweep up trash on a city sidewalk they should certainly never be given any job that requires a brain or manners or communication with human beings, what a disgrace to the human race. Your criminal chiselers and should be put out to pasture

Great flight. Friendly staff. Free snacks and drinks would be nice. I would love fewer taxes and fees added on.

My 90 year old father flew with me. He needed wheel chair assistance and is nearly deaf. The staff was amazing with him.

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.

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

Information on your arrival and departure airports