ORL - SWF

$69 Find Cheap Flights from Orlando to Stewart Intl. - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$143
Typical prices: $139-$264
Breeze Airways
Sun 1/21Tue 1/23
MCO - SWF • Non-stop
Cheapest non-stop
$152
Typical prices: $133-$241
Breeze Airways
Wed 1/10Sun 1/14
MCO - SWF • Non-stop
Nonstop flights
You can fly direct with Allegiant Air and Breeze Airways. Average duration is 2h 51m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 20% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 17 weeks in advance save around 48% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 32% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $264 (round-trip)
Shortest trip • 5h 24m (one-way)
Insights
Insights
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We hope you love your trip to New Windsor!
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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

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
$143Breeze 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
$146Breeze Airways
Sun, Jan 10 - Thu, Jan 14
Breeze Airways Logo
7:20 am - 10:16 amMCO  Orlando-SWF New Windsor Stewart
2h 56mnonstop
Breeze Airways Logo
10:56 am - 2:15 pmSWF  New Windsor Stewart-MCO Orlando
3h 19mnonstop
$152Breeze Airways
Wed, Oct 28 - Sat, Oct 31
Breeze Airways Logo
7:05 am - 11:39 amMCO  Orlando-SWF New Windsor Stewart
4h 34m1 stop Raleigh-Durham
Breeze Airways Logo
12:39 pm - 11:42 pmSWF  New Windsor Stewart-MCO Orlando
11h 03m1 stop Raleigh-Durham
$154Breeze 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
$155Breeze Airways
Fri, Nov 13 - Sat, Nov 14
Breeze Airways Logo
7:20 am - 11:36 amMCO  Orlando-SWF New Windsor Stewart
4h 16m1 stop Charleston
Breeze Airways Logo
12:39 pm - 11:42 pmSWF  New Windsor Stewart-MCO Orlando
11h 03m1 stop Raleigh-Durham
$155Breeze Airways
Fri, Oct 30 - Sat, Oct 31
Breeze Airways Logo
7:20 am - 11:36 amMCO  Orlando-SWF New Windsor Stewart
4h 16m1 stop Charleston
Breeze Airways Logo
12:39 pm - 11:42 pmSWF  New Windsor Stewart-MCO Orlando
11h 03m1 stop Raleigh-Durham
$156Breeze Airways
Fri, Nov 13 - Wed, Nov 18
Multiple Airlines Logo
7:20 am - 11:36 amMCO  Orlando-SWF New Windsor Stewart
4h 16m1 stop Charleston
Multiple Airlines Logo
12:39 pm - 11:25 pmSWF  New Windsor Stewart-MCO Orlando
10h 46m1 stop Raleigh-Durham
$170Multiple Airlines
Wed, Dec 2 - Sat, Dec 5
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
$172Multiple Airlines
Wed, Dec 2 - Sat, Dec 5
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
$172Multiple 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 from Orlando to New Windsor with more confidence.

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

Round-trip flights from Orlando to New Windsor start at $143. Prices are typical for this route right now, with typical round-trip fares ranging from $139 to $264. The lowest price found in the past 5 days was $143 on Breeze Airways.

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 $159 round-trip. Other Orlando to New Windsor routes average $238, based on KAYAK data over the past 12 months.

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

Friday is the cheapest day of the week to fly from Orlando to New Windsor, it is 15% cheaper than the average day. Tuesday is the most expensive day with flight prices 56% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

•September is the cheapest month to fly from Orlando to New Windsor at $129 round-trip.
•June ($234) and November ($229) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 81% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Orlando to New Windsor the cheapest?

Flights from Orlando to New Windsor are cheapest 17 weeks before departure. Booking in this window typically costs about 48% 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

$69
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 24% increase in price.
Flight from Orlando 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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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.

  • What airlines are available from Orlando to New Windsor?

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

    • Allegiant Air
    • Breeze Airways

  • 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 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 travelers should check the fare details before booking.

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

    Two cabin classes are available on flights from Orlando to New Windsor:

    • Economy Class
    • Premium Economy Class

  • 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 $178 round-trip, compared to $264 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.

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

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

    • Charleston (CHS) - 65% of one-stop connections
    • Raleigh-Durham (RDU) - 35% of one-stop connections
    Together, these airports account for 100% of one-stop bookings on this route.

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

    Yes. Being flexible with your travel dates can save you up to 46% on the Orlando to New Windsor route. Friday is the cheapest departure day at $161 round-trip on average, while Tuesday is the most expensive at $294, a difference of $133. 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 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 7:51 am
    • Latest: departs at 5:12 pm and lands at 8:03 pm.

    The flight takes about 2h 51m.

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

    Last-minute fares on this route - booked within 2 weeks of departure - run 33% above the route average of $188. Book 17 weeks before departure for the lowest fares.

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

    A nonstop flight from Orlando to New Windsor takes 2h 51m, 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 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 $74, which is 41% below the typical average for this route.

  • 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 25m, compared with 5h 24m via Raleigh-Durham (RDU).

  • 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 starting from around $30 for economy cars. Top options include:
    • Budget
    • Avis
    • Alamo
    • Empire Rent A Car
    • Enterprise Rent-A-Car

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

    Round-trip flights from Orlando to New Windsor range from $139 to $264, with an average of $188 over the past 12 months. Anything below $139 counts as a good deal.

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 can be flexible, aim for a Friday departure instead of Tuesday. On this route, Friday flights average $161 - about $133 less than Tuesday (45% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 17 weeks before you fly. On this route, that window historically saves about 48% 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 September. Fares historically average $129 round-trip in that month - typically $105 less than the most expensive month, which is June (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

Wednesday

Allegiant Air,Breeze Airways

Allegiant Air,Breeze Airways

Thursday

Breeze Airways

Breeze Airways

Friday

Allegiant Air

Allegiant Air

Sunday

Breeze Airways,Allegiant Air

Breeze Airways,Allegiant Air

See more direct flights

Direct returns

New Windsor Stewart to Orlando

Monday

Allegiant Air

Allegiant Air

Wednesday

Allegiant Air,Breeze Airways

Allegiant Air,Breeze Airways

Thursday

Breeze Airways

Breeze Airways

Friday

Allegiant Air

Allegiant Air

Sunday

Breeze Airways,Allegiant Air

Breeze Airways,Allegiant Air

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