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Isle of Wight

$56+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
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 April, 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 December 16, 2025.

This Priceline deal was found by Cheapflights users on 12/14. 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 12/226:00 amORD - ORF
1 stop6h 09mFrontier
Fri 12/262:34 pmORF - ORD
1 stop8h 50mFrontier
Deal found 12/14$337
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Thu 12/252:50 pmORD - ORF
Nonstop2h 13mAmerican Airlines
Sun 12/287:23 amORF - ORD
Nonstop2h 32mAmerican Airlines
Deal found 12/14$355
This Trip.com deal was found by Cheapflights users on 12/14. 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.
Mon 12/296:00 amORD - ORF
1 stop6h 09mFrontier
Wed 12/3111:44 amORF - ORD
1 stop11h 40mFrontier
Deal found 12/14$363
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/317:25 amORD - ORF
Nonstop2h 13mUnited Airlines
Sun 1/46:30 amORF - ORD
Nonstop2h 35mUnited Airlines
Deal found 12/16$421
This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:00 amORD - ORF
1 stop6h 09mFrontier
Fri 1/22:34 pmORF - ORD
1 stop8h 50mFrontier
Deal found 12/14$442
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/308:00 amORD - ORF
1 stop29h 06mMultiple Airlines
Sat 1/39:39 pmORF - ORD
2 stops14h 59mMultiple Airlines
Deal found 12/15$464
This Priceline deal was found by Cheapflights users on 12/13. 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.
Fri 12/196:00 amORD - ORF
1 stop6h 39mFrontier
Sat 1/35:47 pmORF - ORD
1 stop5h 59mFrontier
Deal found 12/13$467

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 December 16, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$122
(Kiwi.com)

One-way from

$56
(Spirit)

Popular in

December

Cheapest in

January

Average price

$425
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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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 16, 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

Mon 1/12

7:20 am-6:38 pm

1 stop10h 18m

Norfolk

Sat 1/24

6:45 am-5:52 pm

1 stop12h 07m

$162

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 1/5

12:09 pm-6:45 pm

1 stop29h 36m

Norfolk

Sun 1/11

7:33 pm-11:22 am

1 stop16h 49m

$168

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 1/24

12:44 pm-9:50 pm

1 stop8h 06m

Norfolk

Mon 2/2

11:43 am-10:46 pm

1 stop12h 03m

$186

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 1/31

11:05 am-2:25 pm

Nonstop2h 20m

Norfolk

Sat 1/31

7:45 pm-11:39 pm

1 stop4h 54m

$273

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 1/10

11:05 am-2:25 pm

Nonstop2h 20m

Norfolk

Thu 1/22

4:45 pm-6:19 pm

Nonstop2h 34m

$293

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 1/31

7:25 pm-10:32 pm

Nonstop2h 07m

Norfolk

Sat 2/28

7:38 am-9:25 am

Nonstop2h 47m

$300

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 1/29

3:35 pm-11:27 pm

1 stop6h 52m

Norfolk

Sat 1/31

4:45 pm-6:20 pm

Nonstop2h 35m

$303

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 1/7

6:10 pm-9:32 pm

Nonstop2h 22m

Norfolk

Thu 1/22

7:45 pm-11:39 pm

1 stop4h 54m

$303

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 2/21

11:05 am-2:22 pm

Nonstop2h 17m

Norfolk

Mon 2/23

6:00 am-10:49 am

1 stop5h 49m

$303

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 2/27

6:02 pm-9:11 pm

Nonstop2h 09m

Norfolk

Tue 3/3

10:15 am-11:50 am

Nonstop2h 35m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 18 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 December 12, 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 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, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Isle of Wight (average of $121). Flying from Chicago O'Hare Intl Airport to Isle of Wight in December is currently the most expensive (average of $266). 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 December 16, 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 20% 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 December 13, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Isle of Wight flight should consider departing on Saturday evenings 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 December 16, 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
9,092 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,092 reviews
United Airlines
7.4
Good
9,092 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,049 reviews
United Airlines
7.4
Good
9,092 reviews

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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 2h 20m. 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 ($115), 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 (75%), ANA (71%) or United Airlines (71%) 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 $412, our data indicates the cheapest price to be $119. The most popular route (Chicago O'Hare Intl - Norfolk), is priced around $130.

  • 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 $121). Flying from Chicago O'Hare Intl Airport to Isle of Wight in December is currently the most expensive (average of $266). 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.

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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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$207Average$400FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$235Average$394FlexibilityNo cancel feeOn-time71%

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