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Isle of Wight

$67+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Jul 16 — Jul 231
Wed 7/16
Wed 7/23
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 September or April, booked 68 days in advance, depart on a Tuesday or Thursday and return on a Friday

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 July 11, 2025.

Round-trip from

$239
(American Airlines)

One-way from

$67
(Southwest)

Popular in

February

Cheapest in

September

Average price

$397
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. 5% potential increase in price ($19 potential increase over avg. RT price).
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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 July 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 July 11, 2025.

This American Airlines deal was found by Cheapflights users on 7/9. 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.
Fri 9/122:20 pmORD - ORF
Nonstop2h 24mAmerican Airlines
Mon 9/157:01 amORF - ORD
Nonstop2h 34mAmerican Airlines
Deal found 7/9$239
This Booking.com deal was found by Cheapflights users on 7/10. 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.
Fri 7/2510:00 amORD - ORF
1 stop11h 35mSpirit Airlines
Tue 7/295:50 amORF - ORD
1 stop10h 41mSpirit Airlines
Deal found 7/10$240
This Delta deal was found by Cheapflights users on 7/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/25:20 pmORD - ORF
1 stop4h 52mDelta
Mon 8/47:54 pmORF - ORD
1 stop5h 15mDelta
Deal found 7/10$241
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Fri 8/86:22 pmORD - ORF
Nonstop2h 18mUnited Airlines
Sun 8/106:20 amORF - ORD
Nonstop2h 25mUnited Airlines
Deal found 7/9$243
This Southwest deal was found by Cheapflights users on 7/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/182:55 pmORD - ORF
2 stops6h 55mSouthwest
Sat 9/206:20 amORF - ORD
2 stops11h 05mSouthwest
Deal found 7/10$245
This Mytrip deal was found by Cheapflights users on 7/9. 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.
Thu 8/74:36 pmORD - ORF
1 stop15h 54mMultiple Airlines
Tue 8/125:20 pmORF - ORD
3 stops23h 50mMultiple Airlines
Deal found 7/9$250
This Frontier deal was found by Cheapflights users on 7/10. 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.
Sun 8/245:10 amORD - ORF
1 stop9h 08mFrontier
Sun 8/314:12 pmORF - ORD
1 stop8h 42mFrontier
Deal found 7/10$257

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 July 11, 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

Fri 9/12

2:20 pm-5:44 pm

Nonstop2h 24m

Norfolk

Mon 9/15

7:01 am-8:35 am

Nonstop2h 34m

$239

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 7/25

10:00 am-10:35 pm

1 stop11h 35m

Norfolk

Tue 7/29

5:50 am-3:31 pm

1 stop10h 41m

$240

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 8/2

5:20 pm-11:12 pm

1 stop4h 52m

Norfolk

Mon 8/4

7:54 pm-12:09 am

1 stop5h 15m

$241

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 8/8

6:22 pm-9:40 pm

Nonstop2h 18m

Norfolk

Sun 8/10

6:20 am-7:45 am

Nonstop2h 25m

$243

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 9/18

2:55 pm-10:50 pm

2 stops6h 55m

Norfolk

Sat 9/20

6:20 am-4:25 pm

2 stops11h 05m

$245

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 8/7

4:36 pm-9:30 am

1 stop15h 54m

Norfolk

Tue 8/12

5:20 pm-4:10 pm

3 stops23h 50m

$250

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 8/24

5:10 am-3:18 pm

1 stop9h 08m

Norfolk

Sun 8/31

4:12 pm-11:54 pm

1 stop8h 42m

$257

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 9/23

1:50 pm-9:40 pm

1 stop6h 50m

$67

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 8/12

3:40 pm-11:41 pm

1 stop7h 01m

$72

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 7/29

10:00 am-10:35 pm

1 stop11h 35m

$83

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

Showing 1-10 of 14 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 June 27, 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Isle of Wight (average of $281). Flying from Chicago O'Hare Intl Airport to Isle of Wight in March is currently the most expensive (average of $351). 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 July 11, 2025.

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 July 6, 2025.

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

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 July 11, 2025.

The most flights from ORD to I1W are scheduled on a Wednesday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 July 11, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Isle of Wight, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,951 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,846 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Spirit Airlines
6.3
Okay
8,055 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 Southwest ($67), United Airlines ($72), and Spirit Airlines ($83).

  • 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 (92%), Republic Airways (90%) or GoJet (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 $393, our data indicates the cheapest price to be $112. The most popular route (Chicago O'Hare Intl - Norfolk), is priced around $133.

  • 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 $281). Flying from Chicago O'Hare Intl Airport to Isle of Wight in March is currently the most expensive (average of $351). 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 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 July 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$79Average$245FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$366FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$207Average$422FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$213Average$393FlexibilityNo cancel feeOn-time71%

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