$56+ Cheap flights from New Windsor (SWF) to Orlando (ORL)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — ORL
Oct 29 — Nov 51
Round-trip
1 adult, Economy
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Find cheap flights from Stewart to Orlando with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from New Windsor Stewart to Orlando are usually found in May or September, booked 66 days in advance, depart on a Monday or Friday and return on a Friday
Cheap flight deals from Stewart to Orlando
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Best
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Cheapest flights from Stewart to OrlandoExplore the most affordable flight options available from Stewart to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2026.
Explore the most affordable flight options available from Stewart to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2026.
This CheapOair deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:04 pm -
Nonstop2h 49m
Fri 11/208:00 am -
Nonstop2h 39m
Deal found 9/27![Allegiant Air logo]()
$130
This CheapOair deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:03 am -
Nonstop2h 49m
Mon 12/147:30 am -
Nonstop2h 43m
Deal found 9/28![Allegiant Air logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/611:06 am -
Nonstop3h 19m
Thu 12/107:30 am -
Nonstop2h 56m
Deal found 9/24![Breeze Airways logo]()
$142
This Cheapflightsfares deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:29 am -
Nonstop2h 55m
Wed 11/256:00 am -
Nonstop2h 39m
Deal found 9/24![Allegiant Air logo]()
$146
This Booking.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:01 pm -
Nonstop2h 49m
Fri 10/302:03 pm -
Nonstop2h 46m
Deal found 9/24![Allegiant Air logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:01 pm -
Nonstop2h 49m
Fri 10/302:03 pm -
Nonstop2h 46m
Deal found 9/26![Allegiant Air logo]()
$151
This CheapOair deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/411:03 am -
Nonstop2h 49m
Fri 12/117:30 am -
Nonstop2h 43m
Deal found 9/25![Allegiant Air logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:39 pm -
1 stop11h 03m
Fri 10/307:20 am -
1 stop4h 16m
Deal found 9/26![Breeze Airways logo]()
$153
This CheapOair deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:04 pm -
Nonstop2h 49m
Fri 11/131:54 pm -
Nonstop2h 46m
Deal found 9/24![Allegiant Air logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:39 pm -
1 stop11h 03m
Wed 11/47:05 am -
1 stop4h 34m
Deal found 9/28![Breeze Airways logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:39 pm -
1 stop11h 03m
Sun 11/17:20 am -
Nonstop2h 56m
Deal found 9/28![Breeze Airways logo]()
$157
This CheapOair deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1311:06 am -
Nonstop3h 19m
Wed 12/167:05 am -
1 stop4h 34m
Deal found 9/25![Breeze Airways logo]()
$158
Best flights from Stewart to OrlandoDiscover carefully curated flight deals from Stewart to Orlando that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 29, 2026.
Discover carefully curated flight deals from Stewart to Orlando that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 29, 2026.
This CheapOair deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/411:03 am -
Nonstop2h 49m
Fri 12/117:30 am -
Nonstop2h 43m
Deal found 9/25![Allegiant Air logo]()
$152
This Breeze Airways deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/111:58 am -
1 stop4h 47m
Fri 2/56:30 am -
1 stop4h 27m
Deal found 9/26![Breeze Airways logo]()
$164
This CheapOair deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:01 pm -
Nonstop2h 49m
Fri 10/302:03 pm -
Nonstop2h 46m
Deal found 9/29![Allegiant Air logo]()
$160
This CheapOair deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:01 pm -
Nonstop2h 49m
Fri 10/232:03 pm -
Nonstop2h 46m
Deal found 9/26![Allegiant Air logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:39 pm -
1 stop11h 03m
Sat 11/77:05 am -
1 stop4h 34m
Deal found 9/25![Breeze Airways logo]()
$214
This CheapOair deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:01 pm -
Nonstop2h 49m
Mon 11/23:25 pm -
Nonstop2h 46m
Deal found 9/28![Allegiant Air logo]()
$179
This Breeze Airways deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:39 pm -
1 stop11h 03m
Sat 12/57:05 am -
1 stop4h 34m
Deal found 9/27![Breeze Airways logo]()
$215
This CheapOair deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/411:03 am -
Nonstop2h 49m
Mon 12/77:30 am -
Nonstop2h 43m
Deal found 9/26![Allegiant Air logo]()
$182
This FlightHub deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2610:49 am -
Nonstop2h 55m
Mon 3/17:15 am -
Nonstop2h 44m
Deal found 9/25![Allegiant Air logo]()
$197
This Breeze Airways deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:16 pm -
1 stop4h 39m
Sun 11/17:20 am -
Nonstop2h 56m
Deal found 9/25![Breeze Airways logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:29 am -
Nonstop2h 55m
Fri 12/47:30 am -
Nonstop2h 43m
Deal found 9/27![Allegiant Air logo]()
$208
This Breeze Airways deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:16 pm -
1 stop4h 39m
Thu 11/57:20 am -
Nonstop2h 56m
Deal found 9/24![Breeze Airways logo]()
$274
This Breeze Airways deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/110:56 am -
Nonstop3h 19m
Wed 11/47:05 am -
1 stop4h 34m
Deal found 9/27![Breeze Airways logo]()
$275
This CheapOair deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:39 pm -
Nonstop2h 49m
Mon 10/263:25 pm -
Nonstop2h 46m
Deal found 9/24![Allegiant Air logo]()
$241
This Breeze Airways deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:56 am -
Nonstop3h 19m
Sat 10/317:05 am -
1 stop4h 34m
Deal found 9/27![Breeze Airways logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:39 pm -
Nonstop2h 49m
Mon 11/23:25 pm -
Nonstop2h 46m
Deal found 9/28![Allegiant Air logo]()
$244
This Breeze Airways deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3012:39 pm -
1 stop11h 03m
Thu 1/77:20 am -
Nonstop2h 56m
Deal found 9/28![Breeze Airways logo]()
$290
This Travelocity deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/218:50 pm -
Nonstop2h 47m
Mon 12/283:31 pm -
Nonstop2h 40m
Deal found 9/27![Allegiant Air logo]()
$270
This CheapOair deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1912:16 pm -
1 stop4h 39m
Fri 10/237:20 am -
1 stop4h 16m
Deal found 9/25![Breeze Airways logo]()
$300
This Lucky2Go deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:38 am -
2 stops37h 01m
Mon 11/23:25 pm -
Nonstop2h 46m
Deal found 9/27![Allegiant Air logo]()
$285
This Breeze Airways deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1912:39 pm -
1 stop11h 03m
Sun 12/277:30 am -
Nonstop2h 56m
Deal found 9/26![Breeze Airways logo]()
$316
Last-minute flights from Stewart to OrlandoDiscover last-minute flight deals from Stewart to Orlando. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Orlando. Data last updated September 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:39 pm -
1 stop11h 03m
Fri 10/307:20 am -
1 stop4h 16m
Deal found 9/26![Breeze Airways logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:01 pm -
Nonstop2h 49m
Fri 10/302:03 pm -
Nonstop2h 46m
Deal found 9/26![Allegiant Air logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:39 pm -
1 stop11h 03m
Sun 11/17:20 am -
Nonstop2h 56m
Deal found 9/28![Breeze Airways logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:39 pm -
1 stop11h 03m
Thu 10/297:20 am -
Nonstop2h 56m
Deal found 9/28![Breeze Airways logo]()
$162
This Expedia deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:39 pm -
1 stop11h 03m
Wed 10/287:05 am -
1 stop4h 34m
Deal found 9/27![Breeze Airways logo]()
$166
This Booking.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:01 pm -
Nonstop2h 49m
Fri 10/302:03 pm -
Nonstop2h 46m
Deal found 9/24![Allegiant Air logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:01 pm -
Nonstop2h 49m
Mon 11/23:25 pm -
Nonstop2h 46m
Deal found 9/25![Allegiant Air logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:39 pm -
1 stop11h 03m
Fri 10/307:20 am -
1 stop4h 16m
Deal found 9/26![Breeze Airways logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:39 pm -
1 stop11h 03m
Wed 11/47:05 am -
1 stop4h 34m
Deal found 9/28![Breeze Airways logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:39 pm -
1 stop11h 03m
Sun 11/17:20 am -
Nonstop2h 56m
Deal found 9/27![Breeze Airways logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:39 pm -
1 stop11h 03m
Mon 11/27:20 am -
1 stop4h 16m
Deal found 9/29![Breeze Airways logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:39 pm -
1 stop4h 33m
Sun 11/17:20 am -
Nonstop2h 56m
Deal found 9/24![Breeze Airways logo]()
$165
One-way flights from Stewart to OrlandoSearch for one-way flight options from Stewart to Orlando. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
Search for one-way flight options from Stewart to Orlando. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:04 pm -
Nonstop2h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Allegiant Air logo]()
$56
This CheapOair deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:03 am -
Nonstop2h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Allegiant Air logo]()
$58
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:01 pm -
Nonstop2h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Allegiant Air logo]()
$61
This CheapOair deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:04 pm -
Nonstop2h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Allegiant Air logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:29 am -
Nonstop2h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Allegiant Air logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:03 am -
Nonstop2h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Allegiant Air logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1311:06 am -
Nonstop3h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Breeze Airways logo]()
$73
This Booking.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/611:06 am -
Nonstop3h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Breeze Airways logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:39 pm -
1 stop11h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Breeze Airways logo]()
$79
This CheapOair deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:39 pm -
1 stop11h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Breeze Airways logo]()
$81
This CheapOair deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:16 pm -
1 stop4h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Breeze Airways logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:39 pm -
1 stop11h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Breeze Airways logo]()
$86
Find flight deals from Stewart to Orlando
Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Orlando (ORL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $130 (CheapOair) |
One-way from | $56 (Kiwi.com) |
Popular in | March |
Cheapest in | May |
Average price | $182 |
Cheapflights Fare Finder
Customize your flight search to find flights from Stewart to Orlando that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 29, 2026.
Use the filters below to find and compare flights from New Windsor to Orlando that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New WindsorOrlando
SWF New Windsor Stewart - SFB Orlando Sanford Intl
SWFSFB
New Windsor Stewart
Mon 11/16
7:04 pm-9:53 pm
Nonstop2h 49m
Orlando Sanford Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$64
New WindsorOrlando
SWF New Windsor Stewart - SFB Orlando Sanford Intl
SWFSFB
New Windsor Stewart
Mon 11/9
7:04 pm-9:53 pm
Nonstop2h 49m
Orlando Sanford Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$71
New WindsorOrlando
SWF New Windsor Stewart - SFB Orlando Sanford Intl
SWFSFB
New Windsor Stewart
Mon 11/23
11:29 am-2:24 pm
Nonstop2h 55m
Orlando Sanford Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$73
New WindsorOrlando
SWF New Windsor Stewart - SFB Orlando Sanford Intl
SWFSFB
New Windsor Stewart
Mon 10/26
7:01 pm-9:50 pm
Nonstop2h 49m
Orlando Sanford Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$82
New WindsorOrlando
SWF New Windsor Stewart - SFB Orlando Sanford Intl
SWFSFB
New Windsor Stewart
Fri 11/20
11:29 am-2:24 pm
Nonstop2h 55m
Orlando Sanford Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$111
New WindsorOrlando
SWF New Windsor Stewart - MCO Orlando
SWFMCO
New Windsor Stewart
Sat 11/21
12:39 pm-11:42 pm
1 stop11h 03m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$113
New WindsorOrlando
SWF New Windsor Stewart - MCO Orlando
SWFMCO
New Windsor Stewart
Sun 11/22
10:56 am-2:15 pm
Nonstop3h 19m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$119
New WindsorOrlando
SWF New Windsor Stewart - MCO Orlando
SWFMCO
New Windsor Stewart
Thu 12/10
11:06 am-2:25 pm
Nonstop3h 19m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$119
New WindsorOrlando
SWF New Windsor Stewart - MCO Orlando
SWFMCO
New Windsor Stewart
Wed 10/21
12:39 pm-11:42 pm
1 stop11h 03m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$125
New WindsorOrlando
SWF New Windsor Stewart - MCO Orlando
SWFMCO
New Windsor Stewart
Sat 10/24
12:39 pm-9:30 pm
2 stops8h 51m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$132
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Stewart to Orlando
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Orlando in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on New Windsor-Orlando flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Orlando flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Orlando flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on New Windsor-Orlando flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Orlando flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Stewart to Orlando
Have a flexible travel schedule? Discover the best time to fly to Orlando from Stewart with our price prediction graph.
SWF-ORL
SWF-SFB
SWF-MCO
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from New Windsor to Orlando
SWF-ORL
SWF-SFB
SWF-MCO
What is the cheapest month to book a flight from New Windsor to Orlando?
Currently, May is the cheapest month in which you can book a flight from New Windsor to Orlando (average of $183). Flying from New Windsor to Orlando in March is currently the most expensive (average of $292). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SWF to ORL?
Find hourly flight availability from Stewart to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 29, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 56% on flights from New Windsor to Orlando by exploring options for tickets in the morning.
How much does it cost to fly round-trip from New Windsor to Orlando?
Airfare is below average for this route at the moment.
New Windsor to Orlando flights typically cost between $152 and $276 in November.The cheapest round-trip price found within the last 5 days was $130 on Allegiant Air (Nov 16-Nov 20).
How far ahead should I book a flight from New Windsor to Orlando?
The best time to book flights from New Windsor to Orlando is 75 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Orlando
Get insights into the airlines that provide service to Orlando. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orlando. Reviews last updated September 29, 2026.
Read through reviews of airlines operating flights from New Windsor to Orlando, such as Breeze Airways,Allegiant Air, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
6.8
Boarding
8.4
Crew
8.8
Overall
8.2
Entertainment
6.8
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.8
Boarding
8.4
Crew
8.8
Overall
8.2
Entertainment
6.8
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.8
Boarding
8.4
Crew
8.8
Overall
8.2
Entertainment
6.8
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.8
Boarding
8.4
Crew
8.8
Overall
8.2
Entertainment
6.8
Comfort
8.2
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
Find useful and relevant information for your journey from Stewart to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Search flights from Stewart to Orlando by cabin class
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Other flights to Orlando
Explore flights to Orlando departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 29, 2026.
Stewart and Orlando flights
Browse other Stewart and Orlando flight options. Last updated on September 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Stewart to Orlando
Discover the top 3 airlines that operate flights from Stewart to Orlando. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$185 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$161 | Average$258 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$268 | FlexibilityNo cancel fee | On-time62% |