ORL - SWF

$57 Find Cheap Flights from Orlando to Stewart Intl. - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$129
Typical prices: $147-$277
Allegiant Air
Fri 12/7Fri 12/14
SFB - SWF • Non-stop
Cheapest one-way
$57
Typical prices: $93-$174
Allegiant Air
Fri 12/7
SFB - SWF • Non-stop
Nonstop flights
You can fly direct with Breeze Airways and Allegiant Air. Average duration is 2h 50m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 17% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 16 weeks in advance save around 47% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $262 (round-trip)
Shortest trip • 6h 19m (one-way)
Insights
Insights
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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)

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

Recent round-trip flight deals from Orlando to New Windsor

Mon, Dec 7 - Mon, Dec 14
Allegiant Air Logo
7:30 am - 10:13 amSFB  Orlando Sanford Intl-SWF New Windsor Stewart
2h 43mnonstop
Allegiant Air Logo
11:03 am - 1:52 pmSWF  New Windsor Stewart-SFB Orlando Sanford Intl
2h 49mnonstop
$129Allegiant Air
Mon, Dec 7 - Fri, Dec 11
Allegiant Air Logo
7:30 am - 10:13 amSFB  Orlando Sanford Intl-SWF New Windsor Stewart
2h 43mnonstop
Allegiant Air Logo
11:03 am - 1:52 pmSWF  New Windsor Stewart-SFB Orlando Sanford Intl
2h 49mnonstop
$141Allegiant Air
Mon, Dec 7 - Fri, Dec 11
Allegiant Air Logo
7:30 am - 10:13 amSFB  Orlando Sanford Intl-SWF New Windsor Stewart
2h 43mnonstop
Allegiant Air Logo
11:03 am - 1:52 pmSWF  New Windsor Stewart-SFB Orlando Sanford Intl
2h 49mnonstop
$146Allegiant Air
Thu, Dec 3 - Sun, Jan 17
Breeze Airways Logo
7:30 am - 10:26 amMCO  Orlando-SWF New Windsor Stewart
2h 56mnonstop
Breeze Airways Logo
10:56 am - 2:15 pmSWF  New Windsor Stewart-MCO Orlando
3h 19mnonstop
$151Breeze Airways
Fri, Apr 30 - Mon, May 3
Allegiant Air Logo
4:17 pm - 7:05 pmSFB  Orlando Sanford Intl-SWF New Windsor Stewart
2h 48mnonstop
Allegiant Air Logo
7:55 pm - 10:43 pmSWF  New Windsor Stewart-SFB Orlando Sanford Intl
2h 48mnonstop
$151Allegiant Air
Thu, Dec 3 - Sat, Dec 5
Breeze Airways Logo
7:30 am - 10:26 amMCO  Orlando-SWF New Windsor Stewart
2h 56mnonstop
Breeze Airways Logo
12:39 pm - 11:42 pmSWF  New Windsor Stewart-MCO Orlando
11h 03m1 stop Raleigh-Durham
$153Breeze Airways
Thu, Jan 21 - Sat, Jan 23
Breeze Airways Logo
7:20 am - 10:16 amMCO  Orlando-SWF New Windsor Stewart
2h 56mnonstop
Breeze Airways Logo
12:39 pm - 11:42 pmSWF  New Windsor Stewart-MCO Orlando
11h 03m1 stop Raleigh-Durham
$157Breeze Airways
Thu, Dec 3 - Sat, Dec 5
Multiple Airlines Logo
7:30 am - 10:26 amMCO  Orlando-SWF New Windsor Stewart
2h 56mnonstop
Multiple Airlines Logo
12:39 pm - 8:50 pmSWF  New Windsor Stewart-MCO Orlando
8h 11m1 stop Raleigh-Durham
$183Multiple Airlines
Thu, Dec 3 - Sun, Dec 6
Multiple Airlines Logo
7:30 am - 10:26 amMCO  Orlando-SWF New Windsor Stewart
2h 56mnonstop
Multiple Airlines Logo
6:49 pm - 1:47 pmSWF  New Windsor Stewart-MCO Orlando
42h 58m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
$185Multiple Airlines
Wed, Dec 9 - Sat, Dec 12
Multiple Airlines Logo
7:05 am - 11:39 amMCO  Orlando-SWF New Windsor Stewart
4h 34m1 stop Raleigh-Durham
Multiple Airlines Logo
12:39 pm - 8:50 pmSWF  New Windsor Stewart-MCO Orlando
8h 11m1 stop Raleigh-Durham
$216Multiple Airlines
Booking Insights

Price, demand and travel trends for Orlando to New Windsor flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Orlando to New Windsor?

Round-trip flights from Orlando to New Windsor typically range from $147 to $277. The lowest price found in the past 5 days was $129, on Allegiant Air.

What is the cheapest Orlando to New Windsor flight route?

Orlando Sanford Intl Airport (SFB) to New Windsor (SWF) is the cheapest Orlando to New Windsor route, averaging $169 round-trip. Other Orlando to New Windsor routes average $240, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Orlando to New Windsor?

Based on deals KAYAK users found in the last 12 months, Friday is the cheapest day of the week to fly from Orlando to New Windsor. It’s 13% cheaper than the average day, while Tuesday is the most expensive, with prices 40% higher.

What’s the cheapest month to fly from Orlando to New Windsor?

•January is the cheapest month to fly from Orlando to New Windsor at $152 round-trip.
•November ($240) and June ($234) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 57% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Orlando to New Windsor the cheapest?

Flights from Orlando to New Windsor are cheapest 16 weeks before departure. Booking in this window typically costs about 47% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Orlando to New Windsor

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
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.

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.

Key details for Orlando to New Windsor flights

Low season

February

Cheapest flight

$57
Beat the crowds with an average 73% drop in travelers.
The most popular month to fly with an average 68% increase in travelers.
One-way flight from Orlando Sanford Intl Airport to New Windsor

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

Your Orlando to New Windsor flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Orlando to New Windsor?

    These are the earliest and latest flight times available from Orlando to New Windsor:

    • Earliest: departs at 5:00 am and lands at 7:50 am
    • Latest: departs at 5:20 pm and lands at 8:10 pm.

    The flight takes about 2h 50m.

  • What cabin classes can I book on flights from Orlando to New Windsor?

    Only Economy Class is available on flights from Orlando to New Windsor.

  • How long is a flight from Orlando to New Windsor?

    A nonstop flight from Orlando to New Windsor takes 2h 50m, covering 984 miles.

  • Do I need a passport to fly from Orlando to New Windsor?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Orlando to New Windsor flight?

    Round-trip flights from Orlando to New Windsor range from $147 to $277, with an average of $198 over the past 12 months. Anything below $147 counts as a good deal.

  • How expensive are last-minute Orlando to New Windsor flights?

    Last-minute fares on this route (booked within two weeks of departure) run 30% above the $198 route average. Book 16 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Orlando to New Windsor?

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $186 round-trip, compared to $262 via a layover through Charleston (CHS).

  • What is the standard checked-bag allowance on flights from Orlando to New Windsor?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $28–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight prices from Orlando to New Windsor looking right now?

    One-way fares from Orlando to New Windsor are currently lower than usual. Average one-way flight prices are about $84, which is 32% below the typical average for this route.

  • What car rental options are available at New Windsor Stewart Airport (SWF)?

    New Windsor Stewart Airport (SWF) hosts 5 major car rental companies, with daily rates averaging $89 for economy cars. Top options include:

    • Budget
    • Avis
    • Alamo
    • Enterprise Rent-A-Car
    • Empire Rent A Car

  • Which airports can I use when flying from Orlando to New Windsor?

    Flights from Orlando to New Windsor may depart from several airports in Orlando area, including Orlando (MCO) and Orlando Sanford Intl (SFB). Flights usually arrive at New Windsor Stewart (SWF).

  • Which airports do connecting flights from Orlando to New Windsor pass through?

    Connecting flights from Orlando to New Windsor most commonly pass through:

    • Raleigh-Durham (RDU) - 56% of one-stop connections
    • Charleston (CHS) - 44% of one-stop connections

  • Can I save money by using flexible dates for flights from Orlando to New Windsor?

    Yes. Flexible dates can save you up to 38% on flights from Orlando to New Windsor. Friday is the cheapest departure day at $174 round-trip on average, while Tuesday is the most expensive at $278, a difference of $104.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Orlando to New Windsor?

    2 airlines operate flights between Orlando and New Windsor. The airlines offering nonstop flights on this route include:

    • Breeze Airways
    • Allegiant Air

  • How much time can I save by choosing a different layover airport from Orlando to New Windsor?

    Flying via Charleston (CHS) gives the shortest average 1-stop total travel time at 4h 27m, compared with 6h 19m via Raleigh-Durham (RDU).

  • Which airlines offer extra legroom and free seat selection on Orlando to New Windsor flights?

    Among airlines operating Orlando to New Windsor flights:

    • Breeze Airways: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Orlando to New Windsor flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Breeze Airways: a cabin bag and a checked bag in Economy Class
    • Allegiant Air: a checked bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Orlando to New Windsor flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Friday departure and avoid flying on Tuesday. On this route, Friday flights average $174, about $104 less than Tuesday fares (37% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 16 weeks before you fly. On this route, that window historically saves about 47% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Orlando to New Windsor trip for January. Fares historically average $152 round-trip in that month - typically $88 less than the most expensive month, which is November (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to New Windsor Stewart Airport.

    • Homewood Suites by Hilton Newburgh-Stewart Airport

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

More options for your flight from Orlando to New Windsor

Complete your trip to New Windsor with a hotel stay or car rental