HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Isle of Wight

$55+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to Isle of Wight 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 Boston Logan Intl to Isle of Wight are usually found in July or June, booked 69 days in advance, depart on a Monday or Friday and return on a Friday

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 September 11, 2025.

Round-trip from

$109
(Southwest)

One-way from

$55
(Southwest)

Popular in

December

Cheapest in

July

Average price

$197
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. 24% potential increase in price ($80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/45:45 amBOS - ORF
1 stop3h 40mSouthwest
Wed 11/56:15 pmORF - BOS
1 stop4h 00mSouthwest
Deal found 9/10$109
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/15:55 pmBOS - ORF
1 stop3h 25mSouthwest
Tue 11/48:30 amORF - BOS
1 stop4h 25mSouthwest
Deal found 9/11$114
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:35 amBOS - ORF
1 stop5h 50mSouthwest
Mon 10/67:10 pmORF - BOS
1 stop5h 30mSouthwest
Deal found 9/10$132
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/245:40 amBOS - ORF
1 stop4h 10mSouthwest
Tue 9/306:05 amORF - BOS
1 stop4h 25mSouthwest
Deal found 9/9$145
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:53 amBOS - ORF
Nonstop1h 44mJetBlue
Mon 10/610:25 amORF - BOS
Nonstop1h 41mJetBlue
Deal found 9/9$147
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:53 amBOS - ORF
Nonstop1h 44mJetBlue
Thu 10/1610:25 amORF - BOS
Nonstop1h 41mJetBlue
Deal found 9/11$152
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:53 amBOS - ORF
Nonstop1h 44mJetBlue
Sat 9/2710:41 amORF - BOS
Nonstop1h 41mJetBlue
Deal found 9/10$157
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:30 amBOS - ORF
1 stop5h 44mAmerican Airlines
Sat 10/46:00 amORF - BOS
1 stop6h 16mAmerican Airlines
Deal found 9/10$167
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/254:23 pmBOS - ORF
1 stop7h 09mUnited Airlines
Thu 10/26:00 amORF - BOS
1 stop5h 07mUnited Airlines
Deal found 9/10$172
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/275:35 amBOS - ORF
1 stop7h 55mSouthwest
Tue 9/306:05 amORF - BOS
1 stop4h 25mSouthwest
Deal found 9/10$175
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2312:30 pmBOS - ORF
1 stop4h 34mAmerican Airlines
Sun 9/286:00 amORF - BOS
1 stop6h 16mAmerican Airlines
Deal found 9/9$177
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/208:00 amBOS - ORF
Nonstop1h 56mJetBlue
Sat 9/2710:41 amORF - BOS
Nonstop1h 41mJetBlue
Deal found 9/11$182

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 September 11, 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

Tue 12/2

9:10 am-11:12 am

Nonstop2h 02m

Norfolk

Mon 12/8

11:52 am-1:35 pm

Nonstop1h 43m

$147

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 12/3

9:10 am-11:12 am

Nonstop2h 02m

Norfolk

Sun 12/7

11:52 am-1:35 pm

Nonstop1h 43m

$147

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 10/9

5:30 am-9:37 am

1 stop4h 07m

Norfolk

Wed 10/15

7:59 pm-11:59 pm

1 stop4h 00m

$167

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sat 10/11

5:19 pm-11:32 pm

1 stop6h 13m

Norfolk

Tue 10/14

6:00 am-11:08 am

1 stop5h 08m

$183

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 9/24

5:40 am-9:50 am

1 stop4h 10m

Norfolk

Tue 9/30

10:40 am-7:10 pm

2 stops8h 30m

$198

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 10/2

6:05 am-11:32 am

1 stop5h 27m

Norfolk

Sat 10/4

5:30 pm-7:26 pm

Nonstop1h 56m

$207

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Tue 12/2

5:45 am-9:25 am

1 stop3h 40m

Norfolk

Mon 12/8

10:05 am-9:05 pm

2 stops11h 00m

$209

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 12/5

5:45 am-11:40 am

1 stop5h 55m

Norfolk

Sun 12/7

6:15 am-9:45 am

1 stop3h 30m

$210

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 9/25

9:29 am-11:18 am

Nonstop1h 49m

Norfolk

Mon 9/29

6:22 pm-10:20 pm

1 stop3h 58m

$212

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 9/24

9:29 am-11:18 am

Nonstop1h 49m

Norfolk

Tue 9/30

12:13 pm-7:05 pm

1 stop6h 52m

$212

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 23 results
1
2
3

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 August 29, 2025.

The best time to book flights from Boston to Isle of Wight is 69 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, January is the cheapest month in which you can book a flight from Boston to Isle of Wight (average of $281). Flying from Boston 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 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 September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Boston to Isle of Wight as you normally would.

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 September 7, 2025.

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

Weekly flight availability from Boston to Isle of Wight

Explore weekly flight availability from Boston to Isle of Wight. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

The most flights from BOS to I1W are scheduled on a Thursday (32 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Boston to Isle of Wight?

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 September 11, 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
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,913 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Allegiant Air
7.2
Good
702 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 are 2 daily outbound flights to Isle of Wight from 8 different airlines.

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

    A quick flight from Boston to Isle of Wight can take about 2h 02m. Delta provides one of the quickest options available for as low as $147. 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%), Delta (85%) and Republic Airways (85%).

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

    While on average a flight from Boston to Isle of Wight is generally $285, our data shows the cheapest flight currently is $78. When looking at the most popular route, (Boston Logan Intl - Norfolk), you can expect to pay $109 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, January is the cheapest month in which you can book a flight from Boston to Isle of Wight (average of $281). Flying from Boston 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Boston to Isle of Wight

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Reagan-National flights
Boston to Dulles Intl flights
Boston to Raleigh flights
Hartford to Dulles Intl flights
Boston to Richmond flights
Hartford to Reagan-National flights
Boston to Norfolk flights
Hartford to Raleigh flights
Boston to Greensboro flights
Albany to Reagan-National flights
Boston to Charlottesville flights
Albany to Dulles Intl flights
Hartford to Richmond flights
Hartford to Norfolk flights
Boston to Roanoke flights
Hartford to Roanoke flights
Albany to Raleigh flights
Hartford to Greensboro flights
Albany to Norfolk flights
Albany to Greensboro flights
Boston to Newport News flights
Worcester to Raleigh flights
Hartford to Charlottesville flights
Albany to Richmond flights
Hartford to Blountville flights
Boston to Salisbury flights
Hyannis to Reagan-National flights
Albany to Roanoke flights
West Tisbury to Raleigh flights
Hyannis to Raleigh flights
Albany to Charlottesville flights
Boston to Lynchburg flights
West Tisbury to Reagan-National flights
Albany to Blountville flights
Boston to Blountville flights
Nantucket to Reagan-National flights
Worcester to Dulles Intl flights
Boston to Staunton flights
Hartford to Salisbury flights
Hyannis to Dulles Intl flights
Hyannis to Richmond flights
Nantucket to Dulles Intl flights
Hartford to Newport News flights
Hartford to Lynchburg flights
Provincetown to Richmond flights
Albany to Newport News flights
Provincetown to Raleigh flights
West Tisbury to Richmond flights
Provincetown to Reagan-National flights
New Bedford to Raleigh flights

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$49Average$82FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$59Average$189FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$91Average$135FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$104Average$226FlexibilityNo cancel feeOn-time62%
DeltaCheapest$106Average$313FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$156Average$326FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$175Average$325FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$196Average$387FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.