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Isle of Wight

$82+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — RIC
May 31 — Jun 71
Sun 5/31
Sun 6/7
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 63 days in advance, depart on a Monday or Friday and return on a Friday

Cheap 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 May 1, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 6/18:15 am
BOS
-
ORF
Nonstop1h 45m
JetBlue
Wed 6/310:50 am
ORF
-
BOS
Nonstop1h 41m
JetBlue
Deal found 4/30$192
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Mon 6/17:00 am
BOS
-
ORF
1 stop13h 17m
Multiple Airlines
Wed 6/312:06 pm
ORF
-
BOS
1 stop13h 18m
Multiple Airlines
Deal found 4/28$193
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 6/112:01 pm
BOS
-
ORF
1 stop23h 10m
Frontier
Sat 6/612:00 pm
ORF
-
BOS
1 stop13h 24m
Frontier
Deal found 5/1$194
This JetBlue deal was found by Cheapflights users on 4/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/168:39 am
BOS
-
ORF
Nonstop1h 42m
JetBlue
Tue 5/1911:48 am
ORF
-
BOS
Nonstop1h 40m
JetBlue
Deal found 4/27$197
This CheapOair deal was found by Cheapflights users on 5/1. 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 6/18:15 am
BOS
-
ORF
Nonstop1h 45m
JetBlue
Sat 6/610:50 am
ORF
-
BOS
Nonstop1h 39m
JetBlue
Deal found 5/1$198
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 6/38:44 am
BOS
-
ORF
2 stops26h 27m
Frontier
Mon 6/812:06 pm
ORF
-
BOS
1 stop13h 18m
Frontier
Deal found 4/28$201
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Mon 6/14:15 pm
BOS
-
ORF
2 stops7h 29m
United Airlines
Sat 6/65:45 am
ORF
-
BOS
1 stop4h 08m
United Airlines
Deal found 5/1$202
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:47 am
BOS
-
ORF
1 stop4h 55m
American Airlines
Sat 5/161:49 pm
ORF
-
BOS
1 stop4h 28m
American Airlines
Deal found 4/29$207
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/296:00 am
BOS
-
ORF
1 stop29h 15m
Multiple Airlines
Thu 6/49:12 pm
ORF
-
BOS
1 stop24h 30m
Multiple Airlines
Deal found 4/28$210
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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.
Tue 6/28:15 am
BOS
-
ORF
Nonstop1h 45m
JetBlue
Tue 6/165:59 pm
ORF
-
BOS
Nonstop1h 45m
JetBlue
Deal found 5/1$212
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/296:00 am
BOS
-
ORF
1 stop29h 15m
Frontier
Mon 6/112:06 pm
ORF
-
BOS
1 stop19h 43m
Frontier
Deal found 5/1$213
This Super.com deal was found by Cheapflights users on 5/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/78:05 am
BOS
-
ORF
Nonstop1h 44m
JetBlue
Sat 6/135:59 pm
ORF
-
BOS
Nonstop1h 45m
JetBlue
Deal found 5/1$214

Find 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 May 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$192
(Cheapflightsfares)

One-way from

$82
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$213
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. 13% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 1, 2026.
Use the filters below to find and compare flights from Boston to Isle of Wight that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Thu 6/4

6:08 am-7:50 am

Nonstop1h 42m

Norfolk

Mon 6/8

10:50 am-12:29 pm

Nonstop1h 39m

$197

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 6/17

3:21 pm-5:04 pm

Nonstop1h 43m

Norfolk

Wed 6/24

5:59 pm-7:42 pm

Nonstop1h 43m

$237

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Sun 9/6

9:00 am-10:55 am

Nonstop1h 55m

Norfolk

Fri 9/11

6:50 pm-11:22 pm

1 stop4h 32m

$267

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 5/27

5:45 am-9:39 am

1 stop3h 54m

Norfolk

Wed 5/27

5:02 pm-1:14 am

1 stop8h 12m

$267

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 6/12

4:00 pm-10:42 pm

1 stop6h 42m

Norfolk

Sun 6/14

5:54 pm-7:50 pm

Nonstop1h 56m

$267

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 9/11

6:00 am-11:29 am

1 stop5h 29m

Norfolk

Sun 9/13

6:00 am-9:54 am

1 stop3h 54m

$277

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Wed 6/17

6:06 am-11:27 am

1 stop5h 21m

Norfolk

Sun 6/21

11:44 am-1:40 pm

Nonstop1h 56m

$278

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 7/3

9:20 am-11:14 am

Nonstop1h 54m

Norfolk

Fri 7/10

7:09 pm-11:31 pm

1 stop4h 22m

$287

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 6/19

6:00 pm-10:42 pm

1 stop4h 42m

Norfolk

Fri 6/26

7:03 pm-11:27 pm

1 stop4h 24m

$298

BostonNorfolk

BOS - ORF

BOSORF

Boston Logan Intl

Fri 6/19

12:01 pm-11:21 am

1 stop23h 20m

Norfolk

Sun 6/21

12:21 pm-7:52 am

1 stop19h 31m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 24 resultsSorted by cheapest first
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

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 May 1, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 42% 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 April 25, 2026.

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. Sunday mornings 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 May 1, 2026.

The most flights from BOS to I1W are scheduled on a Monday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 May 1, 2026.
Read reviews from past customers who have flown Southwest,Delta, andAllegiant Air 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.
Southwest
8.0
Very good
4,317 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,317 reviews
Southwest
8.0
Very good
4,317 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,464 reviews
Southwest
8.0
Very good
4,317 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Allegiant Air
7.3
Good
707 reviews
Southwest
8.0
Very good
4,317 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,969 reviews
Southwest
8.0
Very good
4,317 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,684 reviews
Southwest
8.0
Very good
4,317 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 7 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 2 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 45m. JetBlue provides one of the quickest options available for as low as $192. Boston and Isle of Wight are separated by a distance of 468 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Boston to Isle of Wight one-way?

    One-way options have recently been found by users for as low as $48 on Allegiant Air. Other airlines that offer cheap prices include Spirit Airlines from $81 and Delta from $83 one-way.

  • 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 Kenya Airways (100%), EL AL (97%) and LATAM Airlines (87%).

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

    While on average a flight from Boston to Isle of Wight is generally $392, our data shows the cheapest flight currently is $113. When looking at the most popular route, (Boston Logan Intl - Norfolk), you can expect to pay $192 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.

See more FAQs

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Top 7 airlines flying from Boston to Isle of Wight

Discover the top 7 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 May 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$48Average$75FlexibilityNo cancel feeOn-time88%
DeltaCheapest$85Average$279FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$97Average$246FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$106Average$159FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$156Average$303FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$296FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$359FlexibilityNo cancel feeOn-time71%

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