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Isle of Wight

$59+ Cheap flights from Chicago (CHI) 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Isle of Wight are usually found in September or November, booked 73 days in advance, depart on a Tuesday or Thursday and return on a Thursday

Cheap flight deals from Chicago to Isle of Wight

Keep the following information in mind while searching for Chicago to Isle of Wight flight deals. Data was last updated September 11, 2025.

Round-trip from

$199
(United Airlines)

One-way from

$59
(Southwest)

Popular in

June

Cheapest in

September

Average price

$312
From Chicago (CHI) to Isle of Wight
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One-way flight from Chicago (CHI) to Isle of Wight
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Highest demand for flights based on searches. 3% potential increase in price ($14 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 September 2025
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Find flight deals from Chicago to Isle of Wight

Cheapest flights from Chicago to Isle of Wight
Explore the most affordable flight options available from Chicago to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/11. 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.
Thu 10/211:20 amORD - ORF
Nonstop2h 20mUnited Airlines
Sun 10/56:30 amORF - ORD
Nonstop2h 25mUnited Airlines
Deal found 9/11$199
This CheapOair deal was found by Cheapflights users on 9/11. 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 9/276:30 amORD - ORF
1 stop9h 13mSpirit Airlines
Mon 10/65:24 amORF - ORD
1 stop6h 26mSpirit Airlines
Deal found 9/11$200
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:10 amORD - ORF
Nonstop2h 32mUnited Airlines
Thu 10/1610:33 amORF - ORD
1 stop7h 10mUnited Airlines
Deal found 9/10$201
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/285:10 amORD - ORF
1 stop5h 09mFrontier
Thu 10/25:12 pmORF - ORD
2 stops19h 46mFrontier
Deal found 9/11$202
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:22 amORD - ORF
Nonstop2h 32mUnited Airlines
Sun 10/56:30 amORF - ORD
Nonstop2h 25mUnited Airlines
Deal found 9/10$204
This Southwest deal was found by Cheapflights users on 9/10. 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.
Wed 10/89:05 amMDW - ORF
2 stops7h 40mSouthwest
Wed 10/159:45 amORF - MDW
2 stops8h 05mSouthwest
Deal found 9/10$205
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/25:10 amORD - ORF
1 stop5h 14mMultiple Airlines
Mon 10/66:53 pmORF - ORD
2 stops24h 45mMultiple Airlines
Deal found 9/11$209
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Wed 10/82:21 pmORD - ORF
Nonstop2h 22mAmerican Airlines
Mon 10/137:00 amORF - ORD
Nonstop2h 29mAmerican Airlines
Deal found 9/11$210
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/42:20 pmORD - ORF
Nonstop2h 24mAmerican Airlines
Mon 10/66:13 pmORF - ORD
Nonstop2h 37mAmerican Airlines
Deal found 9/10$212
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/611:20 amORD - ORF
Nonstop2h 14mUnited Airlines
Mon 12/86:53 pmORF - ORD
1 stop5h 39mUnited Airlines
Deal found 9/10$213
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:58 pmORD - ORF
1 stop13h 04mMultiple Airlines
Mon 10/205:24 amORF - ORD
2 stops19h 20mMultiple Airlines
Deal found 9/10$215
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/255:10 amORD - ORF
1 stop5h 14mFrontier
Mon 9/296:53 pmORF - ORD
2 stops27h 35mFrontier
Deal found 9/11$217

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 September 11, 2025.
Use the filters below to find and compare flights from Chicago to Isle of Wight that are best for you.

Fly from

Chicago

Fly to

Isle of Wight

Route

Depart

Return

Price

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 10/9

6:15 pm-9:38 pm

Nonstop2h 23m

Norfolk

Thu 10/16

7:59 pm-11:15 pm

1 stop4h 16m

$199

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 10/2

4:00 pm-11:32 pm

1 stop6h 32m

Norfolk

Sun 10/5

6:30 am-7:55 am

Nonstop2h 25m

$204

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 10/8

9:05 am-5:45 pm

2 stops7h 40m

Norfolk

Wed 10/15

9:45 am-4:50 pm

2 stops8h 05m

$205

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 12/4

6:00 am-11:58 am

1 stop4h 58m

Norfolk

Sun 12/7

8:10 pm-11:43 pm

1 stop4h 33m

$209

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 12/7

6:30 pm-9:50 pm

Nonstop2h 20m

Norfolk

Tue 12/9

6:10 am-9:36 am

1 stop4h 26m

$210

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 12/6

11:23 am-2:42 pm

Nonstop2h 19m

Norfolk

Mon 12/8

6:00 am-10:42 am

1 stop5h 42m

$220

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 10/24

6:00 am-4:39 pm

1 stop9h 39m

Norfolk

Sun 10/26

12:39 pm-1:24 am

1 stop13h 45m

$220

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 10/15

1:25 pm-4:25 pm

Nonstop2h 00m

Norfolk

Mon 10/20

7:10 pm-8:20 pm

Nonstop2h 10m

$220

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 11/3

4:45 pm-10:52 pm

1 stop5h 07m

Norfolk

Wed 11/5

2:15 pm-3:46 pm

Nonstop2h 31m

$220

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 10/24

6:00 am-4:39 pm

1 stop9h 39m

Norfolk

Mon 10/27

5:24 am-10:50 am

1 stop6h 26m

$226

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 39 results
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Best time to book a flight from Chicago to Isle of Wight

Have a flexible travel schedule? Discover the best time to fly to Isle of Wight from Chicago 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 to Isle of Wight

How far ahead should I book a flight from Chicago to Isle of Wight?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Isle of Wight. Price data was last updated on August 29, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Isle of Wight, you should look to book at least 73 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 Chicago to Isle of Wight?

Currently, January is the cheapest month in which you can book a flight from Chicago to Isle of Wight (average of $281). Flying from Chicago 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 CHI to I1W?

Find hourly flight availability from Chicago 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 September 11, 2025.

When flying from Chicago to Isle of Wight, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Isle of Wight?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Isle of Wight. Price data was last updated on September 7, 2025.

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

Weekly flight availability from Chicago to Isle of Wight

Explore weekly flight availability from Chicago 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 September 11, 2025.

The most flights from CHI to I1W are scheduled on a Thursday (28 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (18 on average).

How much does it cost to fly round-trip from Chicago to Isle of Wight?

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 September 11, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Chicago to Isle of Wight by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 to Isle of Wight?

    United Airlines, Southwest, and American Airlines can get you from Chicago to Isle of Wight in just under 2h 19m. Your travel time can differ by up to 5h 21m. The distance from Chicago to Isle of Wight is about 715 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Isle of Wight one-way?

    $59 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $59 and $74, respectively.

  • What are the most reliable airlines from Chicago to Isle of Wight?

    The top 3 most reliable airlines when flying from Chicago to Isle of Wight are Republic Airways (80%), GoJet (77%) and United Airlines (75%).

  • What are the cheapest flights from Chicago to Isle of Wight?

    The cheapest flight price from Chicago to Isle of Wight is $96. On average you can expect to pay $334. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $117.

  • Can I find deals for flights from Chicago to Isle of Wight that include hotel bookings?

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

  • How can I find direct flights from Chicago 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 Chicago to Isle of Wight.

  • Can I find deals for business class flights from Chicago to Isle of Wight?

    Yes. Cheapflights offers flight deals from Chicago 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 to Isle of Wight?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Isle of Wight (average of $281). Flying from Chicago 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.

See more FAQs

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Alternative routes for Chicago to Isle of Wight

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Isle of Wight

Discover the top 5 airlines that operate flights from Chicago 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$245FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$366FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$213Average$369FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$217Average$437FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$396FlexibilityNo cancel feeOn-time71%

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