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Isle of Wight

$54+ Cheap flights from O'Hare Intl (ORD) 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Isle of Wight are usually found in January or March, booked 75 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from O'Hare Intl to Isle of Wight

Cheapest flights from O'Hare Intl to Isle of Wight
Explore the most affordable flight options available from O'Hare Intl to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sat 2/284:42 pm
ORD
-
ORF
1 stop16h 55m
Frontier
Mon 3/211:39 am
ORF
-
ORD
1 stop12h 00m
Frontier
Deal found 1/28$135
This Mytrip deal was found by Cheapflights users on 1/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:00 am
ORD
-
ORF
1 stop10h 26m
Spirit Airlines
Wed 2/257:31 pm
ORF
-
ORD
1 stop16h 51m
Spirit Airlines
Deal found 1/28$143
This Mytrip deal was found by Cheapflights users on 1/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:15 am
ORD
-
ORF
1 stop12h 11m
Spirit Airlines
Wed 3/188:41 pm
ORF
-
ORD
1 stop15h 40m
Spirit Airlines
Deal found 1/28$144
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 3/106:36 pm
ORD
-
ORF
1 stop22h 50m
Multiple Airlines
Wed 3/188:41 pm
ORF
-
ORD
1 stop15h 40m
Multiple Airlines
Deal found 1/27$147
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:00 am
ORD
-
ORF
1 stop11h 49m
Multiple Airlines
Mon 2/2311:39 am
ORF
-
ORD
1 stop12h 00m
Multiple Airlines
Deal found 1/28$148
This Mytrip deal was found by Cheapflights users on 1/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:00 am
ORD
-
ORF
1 stop11h 49m
Spirit Airlines
Mon 2/237:31 pm
ORF
-
ORD
1 stop16h 51m
Spirit Airlines
Deal found 1/28$149
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:00 am
ORD
-
ORF
1 stop11h 49m
Multiple Airlines
Thu 2/2611:46 am
ORF
-
ORD
1 stop11h 53m
Multiple Airlines
Deal found 1/28$153
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/195:05 am
ORD
-
ORF
1 stop28h 32m
Frontier
Mon 2/2311:39 am
ORF
-
ORD
1 stop12h 00m
Frontier
Deal found 1/27$154
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:00 am
ORD
-
ORF
1 stop10h 26m
Spirit Airlines
Sun 3/87:31 pm
ORF
-
ORD
1 stop24h 40m
Spirit Airlines
Deal found 1/27$155
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/238:16 pm
ORD
-
ORF
1 stop21h 10m
Multiple Airlines
Fri 2/2711:32 am
ORF
-
ORD
1 stop24h 19m
Multiple Airlines
Deal found 1/27$161

Find flight deals from O'Hare Intl to Isle of Wight

Keep the following information in mind while searching for O'Hare Intl to Isle of Wight flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$135
(Kiwi.com)

One-way from

$54
(Priceline)

Popular in

November

Cheapest in

January

Average price

$270
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Norfolk flights.
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From Chicago O'Hare Intl to Isle of Wight
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One-way flight from Chicago O'Hare Intl to Isle of Wight
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Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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 January 29, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Isle of Wight that are best for you.

Fly from

O'Hare Intl

Fly to

Isle of Wight

Route

Depart

Return

Price

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 3/10

7:00 am-6:26 pm

1 stop10h 26m

Norfolk

Wed 3/18

6:45 am-7:46 pm

2 stops14h 01m

$160

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 3/4

5:15 am-9:50 pm

2 stops15h 35m

Norfolk

Mon 3/9

7:31 pm-11:22 am

1 stop16h 51m

$170

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 2/11

6:02 pm-10:51 am

1 stop15h 49m

Norfolk

Fri 2/13

11:32 am-10:39 pm

1 stop12h 07m

$181

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 3/24

6:36 pm-7:46 pm

1 stop24h 10m

Norfolk

Mon 3/30

11:33 am-8:23 am

1 stop21h 50m

$191

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 4/17

1:27 pm-7:29 pm

1 stop29h 02m

Norfolk

Mon 4/20

8:24 pm-11:27 am

1 stop16h 03m

$201

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 3/12

9:15 am-7:46 pm

1 stop9h 31m

Norfolk

Sun 3/15

8:41 pm-11:21 am

1 stop15h 40m

$209

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 2/11

5:15 am-5:20 pm

2 stops11h 05m

Norfolk

Fri 2/13

11:32 am-10:39 pm

1 stop12h 07m

$225

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 4/17

5:30 am-4:53 pm

1 stop10h 23m

Norfolk

Mon 4/20

8:24 pm-11:27 am

1 stop16h 03m

$226

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 4/29

1:27 pm-7:29 pm

1 stop29h 02m

Norfolk

Sun 5/3

8:24 pm-10:44 am

2 stops15h 20m

$244

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 2/24

7:00 am-6:26 pm

1 stop10h 26m

$54

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 21 results
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Best time to book a flight from O'Hare Intl to Isle of Wight

Have a flexible travel schedule? Discover the best time to fly to Isle of Wight from O'Hare Intl 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 Chicago O'Hare Intl Airport to Isle of Wight

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Isle of Wight?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Isle of Wight. Price data was last updated on January 23, 2026.

The price you pay for your flight from Chicago O'Hare Intl Airport to Isle of Wight may vary depending on when you book. For the best chance of a lower fare, look to book 75 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Isle of Wight?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Isle of Wight (average of $134). Flying from Chicago O'Hare Intl Airport to Isle of Wight in December is currently the most expensive (average of $265). 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 ORD to I1W?

Find hourly flight availability from O'Hare Intl 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 January 29, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport to Isle of Wight as you normally would.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Isle of Wight?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Isle of Wight. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Isle of Wight flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Isle of Wight

Explore weekly flight availability from O'Hare Intl 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 January 29, 2026.

The most flights from ORD to I1W are scheduled on a Thursday (19 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (13 on average).

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 January 29, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Isle of Wight, such as United Airlines, American Airlines, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,215 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,205 reviews
United Airlines
7.4
Good
9,215 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Frontier
5.7
Fair
3,056 reviews
United Airlines
7.4
Good
9,215 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl 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.

  • How long is the flight from Chicago O'Hare Intl Airport to Isle of Wight?

    Departing from Chicago O'Hare Intl Airport to Isle of Wight will take you 10h 26m. Chicago O'Hare Intl Airport and Isle of Wight are separated by a distance of 715 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Isle of Wight one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Isle of Wight are Frontier ($93), American Airlines ($118), and United Airlines ($132).

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Isle of Wight?

    No one likes to see their flight delayed. When booking a flight from Chicago O'Hare Intl Airport to Isle of Wight consider choosing Envoy Air (78%), Republic Airways (66%) or ANA (62%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Isle of Wight?

    Looking for the cheapest flight from Chicago O'Hare Intl Airport to Isle of Wight? While on average our users pay $383, our data indicates the cheapest price to be $124. The most popular route (Chicago O'Hare Intl - Norfolk), is priced around $143.

  • Can I find deals for flights from O'Hare Intl to Isle of Wight that include hotel bookings?

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

  • How can I find direct flights from O'Hare Intl 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 O'Hare Intl to Isle of Wight.

  • Can I find deals for business class flights from O'Hare Intl to Isle of Wight?

    Yes. Cheapflights offers flight deals from O'Hare Intl 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 Chicago O'Hare Intl Airport to Isle of Wight?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Isle of Wight (average of $134). Flying from Chicago O'Hare Intl Airport to Isle of Wight in December is currently the most expensive (average of $265). 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

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Alternative routes for O'Hare Intl to Isle of Wight

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from O'Hare Intl to Isle of Wight

Discover the top 4 airlines that operate flights from O'Hare Intl 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
FrontierCheapest$102Average$234FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$207Average$396FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$237Average$394FlexibilityNo cancel feeOn-time71%

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