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Isle of Wight

$139+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — RIC
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$258
(Kiwi.com)

One-way from

$139
(Kiwi.com)

Popular in

December

Cheapest in

June

Average price

$229
From New Windsor Stewart to Isle of Wight
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One-way flight from New Windsor Stewart to Isle of Wight
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Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/2411:31 amSWF - ORF
2 stops24h 56mMultiple Airlines
Mon 10/275:24 amORF - SWF
1 stop8h 47mMultiple Airlines
Deal found 9/8$258
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/3111:31 amSWF - ORF
1 stop11h 15mMultiple Airlines
Sun 11/29:36 pmORF - SWF
1 stop14h 08mMultiple Airlines
Deal found 9/11$268
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/2411:31 amSWF - ORF
1 stop11h 15mMultiple Airlines
Sun 10/267:00 amORF - SWF
1 stop11h 21mMultiple Airlines
Deal found 9/9$293
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/27:11 pmSWF - ORF
2 stops16h 13mMultiple Airlines
Sun 10/57:00 amORF - SWF
1 stop11h 21mMultiple Airlines
Deal found 9/11$326
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 9/2111:43 amSWF - ORF
2 stops23h 41mMultiple Airlines
Sun 9/289:36 pmORF - SWF
1 stop14h 08mMultiple Airlines
Deal found 9/8$351
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/257:12 pmSWF - ORF
2 stops16h 12mMultiple Airlines
Sun 9/289:36 pmORF - SWF
1 stop14h 08mMultiple Airlines
Deal found 9/11$363
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/1912:24 pmSWF - ORF
2 stops20h 12mMultiple Airlines
Sat 9/205:38 pmORF - SWF
1 stop17h 25mMultiple Airlines
Deal found 9/11$475
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/1912:24 pmSWF - ORF
2 stops20h 12mBreeze Airways
Sun 9/219:36 pmORF - SWF
1 stop14h 08mBreeze Airways
Deal found 9/11$487
This Gotogate deal was found by Cheapflights users on 9/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:24 pmSWF - ORF
2 stops9h 38mBreeze Airways
Sun 11/29:36 pmORF - SWF
1 stop14h 08mBreeze Airways
Deal found 9/11$511

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 September 11, 2025.
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 10/24

11:31 am-12:27 pm

2 stops24h 56m

Norfolk

Mon 10/27

5:24 am-2:11 pm

1 stop8h 47m

$258

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Fri 10/31

11:31 am-10:46 pm

1 stop11h 15m

Norfolk

Sun 11/2

9:36 pm-11:44 am

1 stop14h 08m

$268

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Fri 10/24

11:31 am-10:46 pm

1 stop11h 15m

Norfolk

Sun 10/26

7:00 am-6:21 pm

1 stop11h 21m

$293

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Thu 10/2

7:11 pm-11:24 am

2 stops16h 13m

Norfolk

Sun 10/5

7:00 am-6:21 pm

1 stop11h 21m

$326

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Sun 9/21

11:43 am-11:24 am

2 stops23h 41m

Norfolk

Sun 9/28

9:36 pm-11:44 am

1 stop14h 08m

$351

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Thu 9/25

7:12 pm-11:24 am

2 stops16h 12m

Norfolk

Sun 9/28

9:36 pm-11:44 am

1 stop14h 08m

$363

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Fri 9/19

12:24 pm-8:36 am

2 stops20h 12m

Norfolk

Sat 9/20

5:38 pm-11:03 am

1 stop17h 25m

$475

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Fri 9/19

12:24 pm-8:36 am

2 stops20h 12m

Norfolk

Sun 9/21

9:36 pm-11:44 am

1 stop14h 08m

$487

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Wed 11/26

12:17 pm-5:01 pm

2 stops28h 44m

Norfolk

Sun 11/30

9:36 pm-11:44 am

1 stop14h 08m

$558

New WindsorNorfolk

SWF - ORF

SWFORF

New Windsor Stewart

Fri 10/3

12:11 pm-10:48 pm

1 stop10h 37m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 18 results
1
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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, January is the cheapest month in which you can book a flight from New Windsor to Isle of Wight (average of $281). Flying from New Windsor to Isle of Wight in March is currently the most expensive (average of $351). 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 I1W?

Find hourly flight availability from Stewart to Isle of Wight. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

When flying from New Windsor to Isle of Wight, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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, January is the cheapest month in which you can book a flight from New Windsor to Isle of Wight (average of $281). Flying from New Windsor to Isle of Wight in March is currently the most expensive (average of $351). 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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