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Isle of Wight

$68+ Cheap flights from Boston (BOS) 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Isle of Wight are usually found in June or July, booked 73 days in advance, depart on a Monday or Friday and return on a Friday

Find flight deals from Boston to Isle of Wight

Cheapest flights from Boston to Isle of Wight
Explore the most affordable flight options available from Boston to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Southwest deal was found by Cheapflights users on 10/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/105:35 amBOS - ORF
1 stop3h 50mSouthwest
Mon 11/104:15 pmORF - BOS
1 stop4h 30mSouthwest
Deal found 10/27$177
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:16 amBOS - ORF
1 stop12h 42mSpirit Airlines
Thu 11/139:03 pmORF - BOS
1 stop15h 01mSpirit Airlines
Deal found 10/27$183
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/115:45 amBOS - ORF
1 stop3h 40mSouthwest
Sat 11/154:10 pmORF - BOS
1 stop3h 25mSouthwest
Deal found 10/28$184
This Southwest deal was found by Cheapflights users on 10/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/165:35 amBOS - ORF
1 stop3h 50mSouthwest
Wed 11/196:15 pmORF - BOS
1 stop4h 00mSouthwest
Deal found 10/27$194
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/1712:20 pmBOS - ORF
2 stops29h 18mMultiple Airlines
Mon 1/128:32 pmORF - BOS
1 stop13h 36mMultiple Airlines
Deal found 10/27$195
This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:55 pmBOS - ORF
1 stop3h 40mSouthwest
Mon 11/176:15 pmORF - BOS
1 stop4h 00mSouthwest
Deal found 10/29$197
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:48 amBOS - ORF
Nonstop1h 59mDelta
Sun 12/1412:27 pmORF - BOS
Nonstop1h 43mDelta
Deal found 10/28$199
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:48 amBOS - ORF
Nonstop1h 59mDelta
Mon 12/812:27 pmORF - BOS
Nonstop1h 43mDelta
Deal found 10/28$200
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/126:16 amBOS - ORF
1 stop12h 42mMultiple Airlines
Thu 11/133:20 pmORF - BOS
2 stops17h 08mMultiple Airlines
Deal found 10/27$202
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/196:16 amBOS - ORF
2 stops15h 47mMultiple Airlines
Sun 11/232:10 pmORF - BOS
1 stop19h 54mMultiple Airlines
Deal found 10/28$206
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/191:35 pmBOS - ORF
1 stop7h 30mSouthwest
Sat 11/221:50 pmORF - BOS
1 stop9h 00mSouthwest
Deal found 10/28$209
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 11/205:45 pmBOS - ORF
1 stop26h 46mSpirit Airlines
Wed 12/39:26 pmORF - BOS
1 stop12h 37mSpirit Airlines
Deal found 10/27$212

Cheap flight deals from Boston to Isle of Wight

Keep the following information in mind while searching for Boston to Isle of Wight flight deals. Data was last updated October 29, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$168
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$247
Provider with most accurate pricing for Boston Logan Intl-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Norfolk flights.
Search Deals
From Boston Logan Intl to Isle of Wight
Search Deals
One-way flight from Boston Logan Intl to Isle of Wight
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston 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 October 29, 2025.
Use the filters below to find and compare flights from Boston to Isle of Wight that are best for you.

Fly from

Boston

Fly to

Isle of Wight

Route

Depart

Return

Price

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sun 11/16

5:35 am-9:25 am

1 stop3h 50m

Norfolk

Wed 11/19

6:15 pm-10:15 pm

1 stop4h 00m

$194

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 11/14

7:55 pm-11:35 pm

1 stop3h 40m

Norfolk

Sat 11/15

4:10 pm-9:55 pm

1 stop5h 45m

$197

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 12/11

9:48 am-11:47 am

Nonstop1h 59m

Norfolk

Sun 12/14

12:27 pm-2:10 pm

Nonstop1h 43m

$199

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Tue 12/2

9:48 am-11:47 am

Nonstop1h 59m

Norfolk

Sat 12/6

1:15 pm-3:08 pm

Nonstop1h 53m

$199

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 12/12

9:48 am-11:47 am

Nonstop1h 59m

Norfolk

Sun 12/14

12:27 pm-2:10 pm

Nonstop1h 43m

$199

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sat 12/13

5:35 am-9:15 am

1 stop3h 40m

Norfolk

Mon 12/15

10:05 am-7:20 pm

2 stops9h 15m

$222

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 12/3

9:48 am-11:47 am

Nonstop1h 59m

Norfolk

Sun 12/7

5:40 am-11:59 am

1 stop6h 19m

$228

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 11/27

6:05 am-11:29 am

1 stop5h 24m

Norfolk

Wed 12/3

12:27 pm-2:10 pm

Nonstop1h 43m

$228

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 12/4

9:48 am-11:47 am

Nonstop1h 59m

Norfolk

Mon 12/8

4:58 pm-11:55 pm

1 stop6h 57m

$229

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 11/19

1:35 pm-9:05 pm

1 stop7h 30m

$76

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 21 results
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Best time to book a flight from Boston to Isle of Wight

Have a flexible travel schedule? Discover the best time to fly to Isle of Wight from Boston 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 Boston to Isle of Wight

How far ahead should I book a flight from Boston to Isle of Wight?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Isle of Wight. Price data was last updated on October 24, 2025.

The best time to book flights from Boston to Isle of Wight is 73 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.

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

Currently, July is the cheapest month in which you can book a flight from Boston to Isle of Wight (average of $52). Flying from Boston to Isle of Wight in October is currently the most expensive (average of $103). 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 BOS to I1W?

Find hourly flight availability from Boston 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 October 29, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 43% on flights from Boston to Isle of Wight by exploring options for tickets in the evening.

What is the cheapest day to fly from Boston to Isle of Wight?

Use this chart to determine the cheapest time to fly round-trip from Boston to Isle of Wight. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Boston to Isle of Wight flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Isle of Wight

Get insights into the airlines that provide service to Isle of Wight. 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 Isle of Wight. Reviews last updated October 29, 2025.
Read reviews from past customers who have flown Delta, American Airlines, and JetBlue from Boston to Isle of Wight. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,993 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,993 reviews
Delta
7.9
Good
7,993 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,030 reviews
Delta
7.9
Good
7,993 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
JetBlue
7.2
Good
2,907 reviews
Delta
7.9
Good
7,993 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Allegiant Air
7.2
Good
695 reviews
Delta
7.9
Good
7,993 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,113 reviews
Delta
7.9
Good
7,993 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Boston 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 Boston to Isle of Wight?

    Located just 2.6 mi from the city center, Boston Logan Intl is the airport most travelers will use when flying to Isle of Wight from Boston. Booking flights from Logan Intl (BOS) to Isle of Wight should be relatively easy as there is 1 daily outbound flight to Isle of Wight from 8 different airlines.

  • How popular is this Boston to Isle of Wight flight route?

    The Boston Logan Intl to Isle of Wight flight path was viewed by 1 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Boston to Isle of Wight?

    A quick flight from Boston to Isle of Wight can take about 1h 59m. Southwest provides one of the quickest options available for as low as $199. Boston and Isle of Wight are separated by a distance of 468 mi. This flight may include one or multiple stops.

  • What are the most reliable airlines from Boston to Isle of Wight?

    The top 3 most reliable airlines when flying from Boston to Isle of Wight are Aeromexico (100%), ITA Airways (81%) and Delta (77%).

  • What are the cheapest flights from Boston to Isle of Wight?

    While on average a flight from Boston to Isle of Wight is generally $244, our data shows the cheapest flight currently is $88. When looking at the most popular route, (Boston Logan Intl - Norfolk), you can expect to pay $168 for that flight.

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

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

  • How can I find direct flights from Boston 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 Boston to Isle of Wight.

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

    Yes. Cheapflights offers flight deals from Boston 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 Boston to Isle of Wight?

    Currently, July is the cheapest month in which you can book a flight from Boston to Isle of Wight (average of $52). Flying from Boston to Isle of Wight in October is currently the most expensive (average of $103). 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.

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Top 8 airlines flying from Boston to Isle of Wight

Discover the top 8 airlines that operate flights from Boston to Isle of Wight. 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 2,558,603 searches. Data last updated October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$82FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$59Average$200FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$91Average$159FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$104Average$310FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$105Average$226FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$156Average$316FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$358FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$166Average$334FlexibilityNo cancel feeOn-time71%

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