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Isle of Wight

$106+ Cheap flights from New Windsor (SWF) to Isle of Wight, VA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — RIC
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
1 adult, Economy
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Cheap flight deals from Stewart to Isle of Wight

Cheapest flights from Stewart to Isle of Wight
Explore the most affordable flight options available from Stewart to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 14, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/12. 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 5/811:45 am
SWF
-
ORF
1 stop11h 13m
Multiple Airlines
Sun 5/106:43 pm
ORF
-
SWF
1 stop16h 12m
Multiple Airlines
Deal found 2/12$248
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Thu 3/1910:29 am
SWF
-
ORF
1 stop9h 17m
Multiple Airlines
Sat 3/218:41 pm
ORF
-
SWF
1 stop12h 58m
Multiple Airlines
Deal found 2/11$251
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Thu 3/510:09 am
SWF
-
ORF
1 stop8h 17m
Multiple Airlines
Sat 3/78:44 pm
ORF
-
SWF
1 stop11h 35m
Multiple Airlines
Deal found 2/12$267
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
Thu 3/1210:09 am
SWF
-
ORF
1 stop9h 37m
Multiple Airlines
Sun 3/159:30 pm
ORF
-
SWF
1 stop14h 01m
Multiple Airlines
Deal found 2/13$297
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Thu 5/711:45 am
SWF
-
ORF
1 stop7h 47m
Multiple Airlines
Fri 5/810:08 pm
ORF
-
SWF
2 stops13h 17m
Multiple Airlines
Deal found 2/12$320
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Thu 6/1110:28 am
SWF
-
ORF
1 stop9h 01m
Multiple Airlines
Sun 6/145:48 pm
ORF
-
SWF
1 stop15h 01m
Multiple Airlines
Deal found 2/11$323
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/1210:09 am
SWF
-
ORF
1 stop9h 37m
Multiple Airlines
Thu 3/191:17 pm
ORF
-
SWF
2 stops19h 35m
Multiple Airlines
Deal found 2/10$325
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Thu 6/49:38 am
SWF
-
ORF
1 stop28h 42m
Multiple Airlines
Wed 6/106:05 am
ORF
-
SWF
1 stop26h 53m
Multiple Airlines
Deal found 2/11$347
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 2/2011:04 am
SWF
-
ORF
1 stop10h 46m
Multiple Airlines
Sun 2/229:30 pm
ORF
-
SWF
1 stop14h 01m
Multiple Airlines
Deal found 2/11$358
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 6/512:15 pm
SWF
-
ORF
2 stops10h 23m
Breeze Airways
Sun 6/79:50 pm
ORF
-
SWF
1 stop13h 45m
Breeze Airways
Deal found 2/9$365

Find flight deals from Stewart to Isle of Wight

Keep the following information in mind while searching for Stewart to Isle of Wight flight deals. Data was last updated February 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$248
(Kiwi.com)

One-way from

$106
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$209
Provider with most accurate pricing for New York (NYC)-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Norfolk flights.
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From New Windsor Stewart to Isle of Wight
Search Deals
One-way flight from New Windsor Stewart to Isle of Wight
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Isle of Wight 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 2,558,603 searches. Data last updated February 14, 2026.
Use the filters below to find and compare flights from New Windsor to Isle of Wight that are best for you.

Fly from

Stewart

Fly to

Isle of Wight

Route

Depart

Return

Price

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Fri 5/8

11:45 am-10:58 pm

1 stop11h 13m

Norfolk

Sun 5/10

6:43 pm-10:55 am

1 stop16h 12m

$248

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Thu 3/19

10:29 am-7:46 pm

1 stop9h 17m

Norfolk

Sat 3/21

8:41 pm-9:39 am

1 stop12h 58m

$251

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Thu 3/5

10:09 am-6:26 pm

1 stop8h 17m

Norfolk

Sat 3/7

8:44 pm-8:19 am

1 stop11h 35m

$267

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Thu 3/12

10:09 am-7:46 pm

1 stop9h 37m

Norfolk

Sun 3/15

9:30 pm-11:31 am

1 stop14h 01m

$297

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Thu 5/7

11:45 am-7:32 pm

1 stop7h 47m

Norfolk

Fri 5/8

10:08 pm-11:25 am

2 stops13h 17m

$320

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Thu 3/12

10:09 am-7:46 pm

1 stop9h 37m

Norfolk

Thu 3/19

1:17 pm-8:52 am

2 stops19h 35m

$325

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Fri 2/20

11:04 am-9:50 pm

1 stop10h 46m

Norfolk

Sun 2/22

9:30 pm-11:31 am

1 stop14h 01m

$358

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Thu 3/5

10:09 am-6:26 pm

1 stop8h 17m

Norfolk

Sun 3/8

9:30 pm-11:31 am

1 stop14h 01m

$379

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Wed 2/18

5:46 pm-10:51 am

2 stops17h 05m

Norfolk

Thu 2/19

9:30 pm-11:31 am

1 stop14h 01m

$387

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Fri 4/3

12:11 pm-9:47 pm

2 stops9h 36m

Norfolk

Wed 4/8

8:41 pm-10:55 am

1 stop14h 14m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/13

Showing 1-10 of 19 results
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Best time to book a flight from Stewart to Isle of Wight

Have a flexible travel schedule? Discover the best time to fly to Isle of Wight from Stewart with our price prediction graph.
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 Isle of Wight

What is the cheapest month to book a flight from New Windsor to Isle of Wight?

Currently, May is the cheapest month in which you can book a flight from New Windsor to Isle of Wight (average of $97). Flying from New Windsor to Isle of Wight in March is currently the most expensive (average of $179). 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.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Isle of Wight. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Windsor to Isle of Wight?

    For a flight from New Windsor to Isle of Wight, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city. Stewart is the only New Windsor airport and it handles 0 outbound flights to Isle of Wight per day. 0 airlines have flights to Isle of Wight from New Windsor Stewart on a regular basis.

  • Can I find deals for flights from Stewart to Isle of Wight that include hotel bookings?

    Yes. In addition to deals on Stewart to Isle of Wight flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Isle of Wight?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Isle of Wight.

  • Can I find deals for business class flights from Stewart to Isle of Wight?

    Yes. Cheapflights offers flight deals from Stewart to Isle of Wight by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New Windsor to Isle of Wight?

    Currently, May is the cheapest month in which you can book a flight from New Windsor to Isle of Wight (average of $97). Flying from New Windsor to Isle of Wight in March is currently the most expensive (average of $179). 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.

See more FAQs

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