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Isle of Wight

$58+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
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 April or August, booked 68 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap 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 octubre 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$110
(Priceline)

One-way from

$58
(Mytrip)

Popular in

February

Cheapest in

April

Average price

$375
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. 4% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 octubre 30, 2025.

This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/135:25 amORD - ORF
1 stop6h 50mFrontier
jue. 11/133:20 pmORF - ORD
1 stop9h 51mFrontier
Deal found 10/29$110
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/135:25 amORD - ORF
1 stop6h 50mFrontier
lun. 11/1711:29 amORF - ORD
1 stop6h 27mFrontier
Deal found 10/30$127
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/65:01 amORD - ORF
1 stop4h 45mFrontier
jue. 11/133:20 pmORF - ORD
1 stop9h 51mFrontier
Deal found 10/29$143
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/1210:52 amORD - ORF
1 stop7h 06mMultiple Airlines
jue. 11/133:20 pmORF - ORD
1 stop9h 51mMultiple Airlines
Deal found 10/29$158
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/237:09 pmORD - ORF
1 stop13h 34mMultiple Airlines
mar. 12/29:26 pmORF - ORD
1 stop19h 37mMultiple Airlines
Deal found 10/29$167
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/206:23 pmORD - ORF
1 stop25h 08mMultiple Airlines
mar. 12/29:26 pmORF - ORD
1 stop19h 37mMultiple Airlines
Deal found 10/29$172
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
jue. 12/46:15 amORD - ORF
1 stop12h 01mMultiple Airlines
jue. 12/118:38 amORF - ORD
1 stop6h 43mMultiple Airlines
Deal found 10/28$174
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/237:09 pmORD - ORF
1 stop13h 34mMultiple Airlines
lun. 12/19:26 pmORF - ORD
1 stop26h 40mMultiple Airlines
Deal found 10/29$179
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/246:48 amORD - ORF
1 stop12h 43mSpirit Airlines
mar. 12/29:26 pmORF - ORD
1 stop19h 37mSpirit Airlines
Deal found 10/29$181
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/206:23 pmORD - ORF
1 stop25h 08mMultiple Airlines
lun. 12/19:26 pmORF - ORD
1 stop26h 40mMultiple Airlines
Deal found 10/29$183
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/135:25 amORD - ORF
1 stop6h 50mFrontier
dom. 11/161:06 pmORF - ORD
1 stop24h 10mFrontier
Deal found 10/30$185

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 octubre 30, 2025.
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

jue. 11/13

5:11 am-2:25 pm

1 stop8h 14m

Norfolk

lun. 11/17

11:29 am-4:56 pm

1 stop6h 27m

$150

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

sáb. 12/6

7:10 am-7:16 pm

1 stop11h 06m

Norfolk

lun. 12/8

8:38 am-2:21 pm

1 stop6h 43m

$212

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

jue. 12/11

5:00 am-7:16 pm

1 stop13h 16m

Norfolk

jue. 12/18

3:01 pm-12:30 am

1 stop10h 29m

$217

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

jue. 11/13

12:17 pm-6:58 pm

3 stops29h 41m

Norfolk

lun. 11/17

7:53 pm-6:34 pm

2 stops23h 41m

$256

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

mar. 11/25

5:00 am-12:28 pm

1 stop6h 28m

Norfolk

jue. 11/27

9:56 am-2:14 pm

1 stop5h 18m

$296

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

sáb. 12/6

7:10 am-2:25 pm

1 stop6h 15m

Norfolk

lun. 12/8

7:23 am-9:02 am

Nonstop2h 39m

$304

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

jue. 11/27

3:18 pm-6:30 pm

Nonstop2h 12m

Norfolk

jue. 12/4

3:52 pm-7:27 pm

1 stop4h 35m

$305

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

jue. 12/11

5:50 pm-9:00 pm

Nonstop2h 10m

Norfolk

jue. 12/18

6:30 am-8:05 am

Nonstop2h 35m

$313

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

mar. 12/23

5:00 am-2:06 pm

1 stop8h 06m

Norfolk

jue. 1/1

3:01 pm-12:30 am

1 stop10h 29m

$320

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

lun. 1/26

7:00 am-7:37 pm

1 stop11h 37m

$80

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 19 results
1
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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 October 24, 2025.

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 68 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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Isle of Wight (average of $149). Flying from Chicago O'Hare Intl Airport to Isle of Wight in January is currently the most expensive (average of $270). 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 octubre 30, 2025.

It’s typically best to fly out from Chicago O'Hare Intl Airport to Isle of Wight in the evening. Doing so could potentially save you 21% on the flight price compared to flying in the morning, which is usually more expensive.

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 October 26, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Isle of Wight flight should consider departing on Wednesday mornings 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.

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 octubre 30, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Isle of Wight, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

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
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

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
11,035 reviews
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Comfort

7.3

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

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 8h 14m. 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 Spirit Airlines ($95), Frontier ($114), and United Airlines ($129).

  • 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 Republic Airways (92%), Envoy Air (88%) or United Airlines (83%) 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 $322, our data indicates the cheapest price to be $115. The most popular route (Chicago O'Hare Intl - Norfolk), is priced around $141.

  • 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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Isle of Wight (average of $149). Flying from Chicago O'Hare Intl Airport to Isle of Wight in January is currently the most expensive (average of $270). 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 3 airlines flying from O'Hare Intl to Isle of Wight

Discover the top 3 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$218Average$424FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$237Average$395FlexibilityNo cancel feeOn-time71%

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