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Isle of Wight

$56+ Cheap flights from Isle of Wight

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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Jul 22 — Jul 291
Wed 7/22
Wed 7/29
1 adult, Economy
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Find flights from Isle of Wight within your budget

 
Find flights departing from Isle of Wight that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on June 22, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 8/27

6:00 am-9:48 am

1 stop3h 48m

Boston Logan Intl

Thu 9/3

5:45 am-9:34 am

1 stop3h 49m

$207

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Mon 10/19

6:00 am-12:43 pm

1 stop6h 43m

Boston Logan Intl

Tue 10/20

5:45 am-9:42 am

1 stop3h 57m

$207

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 7/23

11:55 am-1:48 pm

Nonstop1h 53m

Boston Logan Intl

Thu 7/30

9:20 am-11:11 am

Nonstop1h 51m

$227

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Sat 9/5

7:59 pm-11:59 pm

1 stop4h 00m

Boston Logan Intl

Tue 9/8

6:00 am-9:53 am

1 stop3h 53m

$227

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Fri 12/4

6:00 am-10:39 am

1 stop4h 39m

Boston Logan Intl

Mon 12/7

6:00 am-9:35 am

1 stop3h 35m

$233

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 9/10

7:09 am-11:18 am

1 stop4h 09m

Boston Logan Intl

Mon 9/14

9:05 am-10:58 am

Nonstop1h 53m

$242
Quickest round-trip

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

Tue 8/4

9:26 am-10:59 am

Nonstop1h 33m

New York LaGuardia

Tue 8/11

12:29 pm-2:01 pm

Nonstop1h 32m

$243

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Tue 7/28

10:31 am-2:23 pm

1 stop3h 52m

Boston Logan Intl

Tue 8/4

9:20 am-11:11 am

Nonstop1h 51m

$247

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Fri 7/3

6:45 pm-8:37 pm

Nonstop1h 52m

Boston Logan Intl

Sun 7/5

3:15 pm-5:14 pm

Nonstop1h 59m

$247

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Sat 8/29

5:44 pm-7:40 pm

Nonstop1h 56m

Boston Logan Intl

Mon 8/31

9:00 am-2:01 pm

1 stop5h 01m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Isle of Wight

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

Travel insights for flights from Isle of Wight

Get recent, data-driven insights about flights from Isle of Wight including ideal travel times, pricing trends, and more.

Which airlines fly from Isle of Wight?

For flights departing from Isle of Wight check dates and pricing for the following: Frontier, Southwest, Breeze Airways, American Airlines, Delta. These airlines depart to the following popular destinations: Orlando.

American Airlines
American Airlines
From $152
Delta
Delta
From $88
United Airlines
United Airlines
From $126
Breeze Airways
Breeze Airways
From $56

When is the cheapest time to fly from Isle of Wight?

Use this chart to determine the cheapest time to fly round-trip from Isle of Wight to Orlando. Price data was last updated on June 20, 2026.

Those who are seeking the cheapest fare on flights departing from Isle of Wight would be wise to consider leaving during Wednesday at noon when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Friday at noon when fares are usually the most expensive.

Airline reviews for flights from Isle of Wight

Read reviews and ratings of airlines operating flights from Isle of Wight. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Isle of Wight travel. Please note that the reviews are sourced from user searches and were last updated on June 22, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
See what other customers who have flown with Breeze Airways,Southwest, andDelta from Isle of Wight have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
293 reviews

Overall

8.2

Entertainment

6.7

Food

6.7

Crew

8.8

Boarding

8.4

Comfort

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.2
Very good
293 reviews
Breeze Airways
8.2
Very good
293 reviews

Overall

8.2

Entertainment

6.7

Food

6.7

Crew

8.8

Boarding

8.4

Comfort

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Southwest
7.9
Good
4,241 reviews
Breeze Airways
8.2
Very good
293 reviews

Overall

8.2

Entertainment

6.7

Food

6.7

Crew

8.8

Boarding

8.4

Comfort

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Delta
7.8
Good
8,424 reviews
Breeze Airways
8.2
Very good
293 reviews

Overall

8.2

Entertainment

6.7

Food

6.7

Crew

8.8

Boarding

8.4

Comfort

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
American Airlines
7.1
Good
11,741 reviews
Breeze Airways
8.2
Very good
293 reviews

Overall

8.2

Entertainment

6.7

Food

6.7

Crew

8.8

Boarding

8.4

Comfort

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Frontier
5.6
Fair
2,870 reviews
Breeze Airways
8.2
Very good
293 reviews

Overall

8.2

Entertainment

6.7

Food

6.7

Crew

8.8

Boarding

8.4

Comfort

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

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Related info for your journey

Access useful and relevant information related to your journey from Isle of Wight. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated June 22, 2026.

  • What is the cheapest airport to fly out of Isle of Wight?

    Istanbul airport offers the cheapest routes to Atlanta, from $23; whereas Cheongju airport is typically cheaper if you're flying to Jeju City, from $24. It's best to make sure you are flexible on dates to find the cheapest possible flight options for your journey.

  • Where are the cheapest places to fly to from Isle of Wight?

    Check out the cheapest flights from Isle of Wight to embark to:
    Fly from Istanbul to Ankara from $23 round trip
    Fly from Medellín to Santa Marta from $24 round trip
    Fly from Cheongju to Jeju City from $24 round trip
    Fly from Santa Marta to Medellín from $24 round trip
    Fly from Medellín to Cartagena from $27 round trip

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