SWF - ORL

$50 Find Cheap Flights from Stewart Intl. to Orlando - Compare and Save

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Everything you should know

Cheapest round-trip
$165
Typical prices: $155-$304
Breeze Airways
Wed 1/17Sat 1/20
SWF - MCO • Non-stop
Cheapest non-stop
$165
Typical prices: $151-$302
Allegiant Air
Fri 11/16Tue 11/20
SWF - SFB • Non-stop
Nonstop flights
You can fly direct with Breeze Airways and Allegiant Air. Average duration is 3h 06m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 15% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 13 weeks in advance save around 37% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $244 (round-trip)
Shortest trip • 4h 26m (one-way)
Insights
Insights
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Expert advice
Flight Deals

Cheap Flights from New Windsor to Orlando (SWF-ORL)

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

Recent round-trip flight deals from New Windsor to Orlando

Sun, Jan 17 - Wed, Jan 20
Breeze Airways Logo
10:56 am - 2:15 pmSWF  New Windsor Stewart-MCO Orlando
3h 19mnonstop
Breeze Airways Logo
7:00 am - 11:39 amMCO  Orlando-SWF New Windsor Stewart
4h 39m1 stop Raleigh-Durham
$165Breeze Airways
Thu, Jan 21 - Sat, Jan 23
Breeze Airways Logo
10:56 am - 2:15 pmSWF  New Windsor Stewart-MCO Orlando
3h 19mnonstop
Breeze Airways Logo
7:00 am - 11:39 amMCO  Orlando-SWF New Windsor Stewart
4h 39m1 stop Raleigh-Durham
$165Breeze Airways
Mon, Nov 16 - Fri, Nov 20
Allegiant Air Logo
7:04 pm - 9:53 pmSWF  New Windsor Stewart-SFB Orlando Sanford Intl
2h 49mnonstop
Allegiant Air Logo
8:00 am - 10:39 amSFB  Orlando Sanford Intl-SWF New Windsor Stewart
2h 39mnonstop
$165Allegiant Air
Mon, Nov 16 - Fri, Nov 20
Allegiant Air Logo
7:04 pm - 9:53 pmSWF  New Windsor Stewart-SFB Orlando Sanford Intl
2h 49mnonstop
Allegiant Air Logo
8:00 am - 10:39 amSFB  Orlando Sanford Intl-SWF New Windsor Stewart
2h 39mnonstop
$166Allegiant Air
Fri, Dec 4 - Mon, Dec 7
Allegiant Air Logo
11:03 am - 1:52 pmSWF  New Windsor Stewart-SFB Orlando Sanford Intl
2h 49mnonstop
Allegiant Air Logo
7:30 am - 10:13 amSFB  Orlando Sanford Intl-SWF New Windsor Stewart
2h 43mnonstop
$166Allegiant Air
Sun, Jan 17 - Fri, Jan 22
Breeze Airways Logo
10:56 am - 2:15 pmSWF  New Windsor Stewart-MCO Orlando
3h 19mnonstop
Breeze Airways Logo
6:30 am - 10:57 amMCO  Orlando-SWF New Windsor Stewart
4h 27m1 stop Charleston
$169Breeze Airways
Sat, Jan 16 - Wed, Jan 20
Breeze Airways Logo
12:39 pm - 11:42 pmSWF  New Windsor Stewart-MCO Orlando
11h 03m1 stop Raleigh-Durham
Breeze Airways Logo
7:00 am - 11:39 amMCO  Orlando-SWF New Windsor Stewart
4h 39m1 stop Raleigh-Durham
$169Breeze Airways
Wed, Dec 2 - Thu, Dec 3
Multiple Airlines Logo
12:39 pm - 8:46 pmSWF  New Windsor Stewart-MCO Orlando
8h 07m1 stop Raleigh-Durham
Multiple Airlines Logo
7:30 am - 10:26 amMCO  Orlando-SWF New Windsor Stewart
2h 56mnonstop
$176Multiple Airlines
Wed, Dec 2 - Sat, Dec 5
Multiple Airlines Logo
12:39 pm - 8:46 pmSWF  New Windsor Stewart-MCO Orlando
8h 07m1 stop Raleigh-Durham
Multiple Airlines Logo
7:05 am - 11:39 amMCO  Orlando-SWF New Windsor Stewart
4h 34m1 stop Raleigh-Durham
$189Multiple Airlines
Mon, Nov 16 - Fri, Nov 20
Multiple Airlines Logo
12:16 pm - 12:20 pmSWF  New Windsor Stewart-SFB Orlando Sanford Intl
48h 04m3 stops Charleston Fort Lauderdale Asheville Regional
Multiple Airlines Logo
8:00 am - 10:39 amSFB  Orlando Sanford Intl-SWF New Windsor Stewart
2h 39mnonstop
$352Multiple Airlines
Booking Insights

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

Round-trip flights from New Windsor to Orlando typically range from $155 to $304. The lowest price found in the past 5 days was $165, on Breeze Airways.

What is the cheapest New Windsor to Orlando flight route?

New Windsor (SWF) to Orlando Sanford Intl Airport (SFB) is the cheapest New Windsor to Orlando route, averaging $187 round-trip. Other New Windsor to Orlando routes average $254, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Monday is the cheapest day of the week to fly from New Windsor to Orlando. It’s 19% cheaper than the average day, while Sunday is the most expensive, with prices 15% higher.

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

•September is the cheapest month to fly from New Windsor to Orlando at $154 round-trip.
•February ($313) and March ($289) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 103% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from New Windsor to Orlando the cheapest?

Flights from New Windsor to Orlando are cheapest 13 weeks before departure. Booking in this window typically costs about 37% 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 New Windsor to Orlando

 
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.

Key details for New Windsor to Orlando flights

Low season

February

Cheapest flight

$49
Beat the crowds with an average 38% drop in travelers.
The most popular month to fly with an average 55% increase in travelers.
One-way flight from New Windsor to Orlando Sanford Intl Airport

When to book flights from New Windsor to Orlando

Are your dates flexible? Find out the best times to travel from New Windsor to Orlando based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your New Windsor to Orlando 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 New Windsor to Orlando?

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

    • Earliest: departs at 8:36 am and lands at 11:42 am
    • Latest: departs at 8:50 pm and lands at 11:56 pm.

    The flight takes about 3h 06m.

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

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

    • Economy Class
    • Premium Economy Class

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

    A nonstop flight from New Windsor to Orlando takes 3h 06m, covering 984 miles.

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

    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 New Windsor to Orlando flight?

    Round-trip flights from New Windsor to Orlando range from $155 to $304, with an average of $222 over the past 12 months. Anything below $155 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 29% above the $222 route average. Book 13 weeks before departure for the lowest fares.

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

    On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $216 round-trip, compared to $244 via a layover through Raleigh-Durham (RDU).

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

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $27–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Have flight prices from New Windsor to Orlando changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $165 to $1,568. That means the highest observed fare was about 10x higher than the lowest one.

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

    One-way fares from New Windsor to Orlando are currently lower than usual. Average one-way flight prices are about $74, which is 43% below the typical average for this route.

  • What car rental options are available in Orlando?

    Since Orlando is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Orlando Airport (MCO) — daily rates averaging $31:

    • Rent-A-Wreck
    • Routes Car & Truck Rentals
    • Hertz
    • Budget
    • Thrifty

    Near Orlando Sanford Intl Airport (SFB) — daily rates averaging $56:

    • Hertz
    • Budget
    • Dollar
    • ADDCAR RENTAL
    • Alamo

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

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

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

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

    • Charleston (CHS) - 63% of one-stop connections
    • Raleigh-Durham (RDU) - 38% of one-stop connections

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

    Yes. Flexible dates can save you up to 30% on flights from New Windsor to Orlando. Monday is the cheapest departure day at $182 round-trip on average, while Sunday is the most expensive at $257, a difference of $75.

    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 New Windsor to Orlando?

    2 airlines operate flights between New Windsor and Orlando. 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 New Windsor to Orlando?

    Flying via Charleston (CHS) gives the shortest average 1-stop total travel time at 4h 26m, compared with 5h 42m via Raleigh-Durham (RDU).

  • What popular places can I visit in Orlando?

    Some of the most popular sights in Orlando are Universal Orlando Resort, Camping World Stadium and Tinker Field. These are among the most viewed places in Orlando on KAYAK.

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

    Among airlines operating New Windsor to Orlando flights:

    • Breeze Airways: offers extra legroom; 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 New Windsor to Orlando 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 New Windsor to Orlando 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 Monday departure and avoid flying on Sunday. On this route, Monday flights average $182, about $75 less than Sunday fares (29% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 13 weeks before you fly. On this route, that window historically saves about 37% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your New Windsor to Orlando trip for September. Fares historically average $154 round-trip in that month - typically $159 less than the most expensive month, which is February (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Orlando Airport.

    • Ramada by Wyndham Suites Orlando Airport
    • Hyatt Regency Orlando International Airport
    • Marriott Orlando Airport Lakeside

Prefer to fly direct from Stewart Intl. to Orlando?

 
Find which airlines fly direct from New Windsor Stewart Airport to Orlando, which days they fly and book direct flights.

Direct departures

New Windsor Stewart to Orlando

Monday

Allegiant Air

Allegiant Air

Tuesday

Breeze Airways

Breeze Airways

Wednesday

Allegiant Air,Breeze Airways

Allegiant Air,Breeze Airways

Thursday

Breeze Airways

Breeze Airways

Friday

Allegiant Air

Allegiant Air

Saturday

Allegiant Air

Allegiant Air

Sunday

Allegiant Air,Breeze Airways

Allegiant Air,Breeze Airways

See more direct flights

Direct returns

Orlando to New Windsor Stewart

Monday

Allegiant Air

Allegiant Air

Tuesday

Breeze Airways

Breeze Airways

Wednesday

Allegiant Air,Breeze Airways

Allegiant Air,Breeze Airways

Thursday

Breeze Airways

Breeze Airways

Friday

Allegiant Air

Allegiant Air

Saturday

Allegiant Air

Allegiant Air

Sunday

Allegiant Air,Breeze Airways

Allegiant Air,Breeze Airways

See more direct flights

More options for your flight from New Windsor to Orlando

Complete your trip to Orlando with a hotel stay or car rental