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Isle of Wight

$43+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORD
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
1 adult, Economy
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What to know about flights from Isle of Wight

Discover essential information about flights departing from Isle of Wight, including flight schedules, destinations, airlines operating at the Isle of Wight airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated November 19, 2025.

Cheapest one-way flight

$39

Cheapest round-trip flight

$83

Cheapest airline

American Airlines

Most popular destination

Atlanta Hartsfield-Jackson (ATL)
The cheapest one-way flight from Isle of Wight is currently to Orlando.
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The cheapest round-trip flight from Isle of Wight is currently to Boston Logan Intl.
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On average, American Airlines currently has the cheapest one-way flight from Isle of Wight (avg. price of $254).
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Atlanta Hartsfield-Jackson (ATL) is currently the most popular flight destination from Isle of Wight (average round-trip price of $266).
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Find flights from Isle of Wight

Cheapest flights from Isle of Wight
Explore the most affordable flight options available from Isle of Wight. Find the lowest fares based on data from user searches, with prices last updated on November 19, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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.
Wed 12/38:02 pmORF - EWR
1 stop13h 00mSpirit Airlines
Sat 12/612:01 pmEWR - ORF
1 stop7h 15mSpirit Airlines
Deal found 11/19$86
This Super.com deal was found by Cheapflights users on 11/19. 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 12/217:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
Wed 12/244:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 11/19$90
This Priceline deal was found by Cheapflights users on 11/17. 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.
Mon 12/158:38 amORF - MCO
Nonstop2h 12mMultiple Airlines
Wed 12/174:51 pmMCO - ORF
Nonstop2h 10mMultiple Airlines
Deal found 11/17$91
This Super.com deal was found by Cheapflights users on 11/17. 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.
Sat 1/37:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
Wed 1/74:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 11/17$92
This Super.com deal was found by Cheapflights users on 11/18. 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.
Fri 12/58:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
Mon 12/85:46 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 11/18$93
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 1/112:29 pmORF - MCO
Nonstop2h 15mFrontier
Sun 1/1811:17 amMCO - ORF
Nonstop2h 06mFrontier
Deal found 11/19$94
This Super.com deal was found by Cheapflights users on 11/17. 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.
Mon 12/158:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
Mon 12/224:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 11/17$95
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:40 pmORF - MCO
1 stop6h 41mFrontier
Sun 12/2112:12 pmMCO - ORF
Nonstop2h 02mFrontier
Deal found 11/19$96
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
Sat 1/249:10 pmORF - MCO
Nonstop2h 15mFrontier
Sun 2/15:25 amMCO - ORF
1 stop5h 23mFrontier
Deal found 11/17$97
This Breeze Airways deal was found by Cheapflights users on 11/18. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:15 amORF - MCO
Nonstop2h 15mBreeze Airways
Fri 12/193:00 pmMCO - ORF
Nonstop2h 10mBreeze Airways
Deal found 11/18$98
This Super.com deal was found by Cheapflights users on 11/19. 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.
Fri 12/58:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
Sun 12/75:46 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 11/19$99
This Priceline deal was found by Cheapflights users on 11/18. 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.
Wed 12/39:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
Thu 12/45:46 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 11/18$100

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 November 19, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

O'Hare Intl

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 12/15

6:15 am-8:30 am

Nonstop2h 15m

Orlando

Fri 12/19

3:00 pm-5:10 pm

Nonstop2h 10m

$98

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 12/14

8:38 am-10:50 am

Nonstop2h 12m

Orlando

Mon 12/22

4:40 pm-6:45 pm

Nonstop2h 05m

$100

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 11/22

5:15 pm-7:30 pm

Nonstop2h 15m

Orlando

Mon 11/24

7:52 pm-10:02 pm

Nonstop2h 10m

$113

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 12/18

7:40 pm-9:58 pm

Nonstop2h 18m

Orlando

Sun 12/21

12:12 pm-2:14 pm

Nonstop2h 02m

$116

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 2/11

4:00 pm-6:10 pm

Nonstop2h 10m

Orlando

Sun 2/15

9:15 am-11:10 am

Nonstop1h 55m

$117

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 12/5

12:00 pm-5:27 pm

1 stop5h 27m

Orlando

Mon 12/15

5:46 am-7:43 am

Nonstop1h 57m

$117

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 12/6

8:11 pm-7:45 am

1 stop11h 34m

Orlando

Fri 12/12

5:46 am-7:43 am

Nonstop1h 57m

$119

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 12/4

8:38 am-10:50 am

Nonstop2h 12m

Orlando

Mon 12/8

5:46 am-7:43 am

Nonstop1h 57m

$120

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 12/3

9:26 pm-11:29 pm

Nonstop2h 03m

Orlando

Thu 12/4

10:02 am-4:47 pm

1 stop6h 45m

$122

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 2/17

7:31 pm-11:54 pm

1 stop4h 23m

Orlando

Sat 2/21

7:50 pm-9:50 pm

Nonstop2h 00m

$127

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 60 results
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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.

When is the best time to book a flight from Isle of Wight?

Use this chart to determine the optimal time to book a round-trip flight from Isle of Wight to O'Hare Intl. Price data was last updated on November 14, 2025.

To ensure you get the cheapest price possible for a flight from Isle of Wight, you should look to book at least 67 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, May is the cheapest month in which you can book a flight from Isle of Wight (average of $108). Flying from Isle of Wight in July will prove the most costly (average of $265). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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 O'Hare Intl. Price data was last updated on November 2, 2025.

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

Which airlines fly from Isle of Wight?

For flights departing from Isle of Wight check dates and pricing for the following: American Airlines, United Airlines, Frontier, Spirit Airlines. These airlines depart to the following popular destinations: Chicago.

American Airlines
American Airlines
From $164
Delta
Delta
From $88
United Airlines
United Airlines
From $150
Southwest
Southwest
From $152

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 November 19, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
See what other customers who have flown with United Airlines, American Airlines, and Spirit Airlines from Isle of Wight have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,019 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,019 reviews
United Airlines
7.4
Good
9,019 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,045 reviews
United Airlines
7.4
Good
9,019 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Spirit Airlines
6.3
Okay
8,151 reviews
United Airlines
7.4
Good
9,019 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Frontier
5.8
Fair
3,105 reviews
United Airlines
7.4
Good
9,019 reviews

Crew

8.1

Boarding

7.7

Overall

7.4

Food

6.6

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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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 November 19, 2025.

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

    Istanbul airport offers the cheapest routes to Cairo, 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.

  • What is the cheapest month to fly from Isle of Wight?

    May is currently the cheapest month to fly from Isle of Wight. At this moment in time July is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • 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 Cheongju to Jeju City from $24 round trip
    Fly from Medellín to Bogotá from $29 round trip
    Fly from Venice to Tirana from $30 round trip
    Fly from Bogotá to Medellín from $33 round trip

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