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Isle of Wight

$53+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 June 30, 2025.

Round-trip from

$235
(Booking.com)

One-way from

$53
(Priceline)

Popular in

June

Cheapest in

September

Average price

$423
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. 4% potential increase in price ($18 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 June 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 June 30, 2025.

This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/910:31 amMDW - ORF
1 stop5h 38mDelta
Mon 8/115:59 pmORF - MDW
1 stop4h 45mDelta
Deal found 6/30$234
This Booking.com deal was found by Cheapflights users on 6/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1410:00 amORD - ORF
1 stop11h 35mSpirit Airlines
Thu 7/175:20 pmORF - ORD
1 stop7h 33mSpirit Airlines
Deal found 6/30$235
This FlightHub deal was found by Cheapflights users on 6/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/215:05 amORD - ORF
1 stop10h 20mMultiple Airlines
Fri 7/2510:25 amORF - ORD
1 stop14h 57mMultiple Airlines
Deal found 6/29$237
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/294:59 pmORD - ORF
1 stop5h 42mAmerican Airlines
Tue 8/57:30 amORF - ORD
Nonstop2h 30mAmerican Airlines
Deal found 6/30$241
This Mytrip deal was found by Cheapflights users on 6/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/142:55 pmMDW - ORF
1 stop17h 18mFrontier
Thu 8/2110:02 pmORF - MDW
1 stop11h 20mFrontier
Deal found 6/30$242
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1710:30 amMDW - ORF
Nonstop2h 05mSouthwest
Fri 9/196:15 pmORF - MDW
Nonstop2h 05mSouthwest
Deal found 6/30$250
This CheapOair deal was found by Cheapflights users on 6/28. 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.
Thu 8/76:16 pmORD - ORF
1 stop13h 57mFrontier
Sun 8/1012:53 pmORF - ORD
1 stop23h 44mFrontier
Deal found 6/28$256
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1411:55 amORD - ORF
Nonstop2h 19mUnited Airlines
Thu 8/215:00 pmORF - ORD
Nonstop2h 25mUnited Airlines
Deal found 6/30$267
This Southwest deal was found by Cheapflights users on 6/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/157:00 amORD - ORF
1 stop9h 30mSouthwest
Sat 9/206:20 amORF - ORD
2 stops11h 05mSouthwest
Deal found 6/28$289

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 June 30, 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

MDW - ORF

MDWORF

Chicago Midway

Sat 8/9

10:31 am-5:09 pm

1 stop5h 38m

Norfolk

Mon 8/11

5:59 pm-9:44 pm

1 stop4h 45m

$234

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 7/14

10:00 am-10:35 pm

1 stop11h 35m

Norfolk

Thu 7/17

5:20 pm-11:53 pm

1 stop7h 33m

$235

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 7/21

5:05 am-4:25 pm

1 stop10h 20m

Norfolk

Fri 7/25

10:25 am-12:22 am

1 stop14h 57m

$237

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 7/29

5:49 pm-10:56 pm

1 stop4h 07m

Norfolk

Tue 8/5

7:30 am-9:00 am

Nonstop2h 30m

$241

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 8/14

2:55 pm-9:13 am

1 stop17h 18m

Norfolk

Thu 8/21

10:02 pm-8:22 am

1 stop11h 20m

$242

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 9/17

10:30 am-1:35 pm

Nonstop2h 05m

Norfolk

Fri 9/19

6:15 pm-7:20 pm

Nonstop2h 05m

$250

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 8/7

6:16 pm-9:13 am

1 stop13h 57m

Norfolk

Sun 8/10

12:53 pm-11:37 am

1 stop23h 44m

$256

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 8/14

11:55 am-3:14 pm

Nonstop2h 19m

Norfolk

Thu 8/21

5:00 pm-6:25 pm

Nonstop2h 25m

$267

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mon 9/15

7:00 am-5:30 pm

1 stop9h 30m

Norfolk

Sat 9/20

6:20 am-4:25 pm

2 stops11h 05m

$289

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 10/8

8:00 am-2:27 pm

1 stop5h 27m

$53

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 20 results
1
2

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 June 27, 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 June 30, 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 June 29, 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 June 30, 2025.

The most flights from CHI to I1W are scheduled on a Monday (28 on average). You will have fewer flight options on Wednesday, 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 June 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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
4,278 reviews

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

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
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

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
7,969 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

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
8,852 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

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.
JetBlue
7.3
Good
2,920 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

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
4,278 reviews

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

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 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.

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

    $53 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Southwest, with prices starting from $93 and $99, 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 (96%), Envoy Air (90%) and Air Canada (82%).

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

    The cheapest flight price from Chicago to Isle of Wight is $112. On average you can expect to pay $325. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $174.

  • 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 June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$79Average$245FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$366FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$207Average$424FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$213Average$384FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$230Average$378FlexibilityNo cancel feeOn-time63%

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