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Isle of Wight

$87+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
4月 5 — 4月 121
土 4/5
土 4/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Isle of Wight are usually found in April or September, booked 73 days in advance, depart on a Tuesday or Thursday and return on a Friday

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 3月 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$238
(Mytrip)

One-way from

$87
(Mytrip)

Popular in

July

Cheapest in

April

Average price

$415
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 (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. 7% potential increase in price ($32 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 March 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 3月 31, 2025.

This Mytrip deal was found by Cheapflights users on 3/30. 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.
木 5/84:35 pmORD - ORF
1 stop16h 54mSpirit Airlines
日 5/115:02 pmORF - ORD
2 stops24h 23mSpirit Airlines
Deal found 3/30$238
This Frontier deal was found by Cheapflights users on 3/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
土 7/266:00 amMDW - ORF
1 stop9h 17mFrontier
土 8/25:06 pmORF - MDW
1 stop7h 15mFrontier
Deal found 3/30$240
This Frontier deal was found by Cheapflights users on 3/31. 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.
土 7/265:10 amORD - ORF
1 stop10h 07mFrontier
土 8/25:06 pmORF - ORD
1 stop8h 16mFrontier
Deal found 3/31$240
This CheapOair deal was found by Cheapflights users on 3/31. 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.
水 4/911:45 amORD - ORF
1 stop27h 46mMultiple Airlines
土 4/128:37 pmORF - ORD
1 stop12h 27mMultiple Airlines
Deal found 3/31$254
This Delta deal was found by Cheapflights users on 3/31. 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.
日 5/251:08 pmMDW - ORF
1 stop3h 33mDelta
水 5/286:42 amORF - MDW
1 stop6h 11mDelta
Deal found 3/31$285
This Delta deal was found by Cheapflights users on 3/31. 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.
日 5/257:10 amORD - ORF
1 stop4h 06mDelta
木 5/297:40 pmORF - ORD
1 stop5h 18mDelta
Deal found 3/31$285
This Southwest deal was found by Cheapflights users on 3/31. 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.
水 5/216:20 amMDW - ORF
1 stop6h 30mSouthwest
土 5/246:30 pmORF - MDW
Nonstop2h 10mSouthwest
Deal found 3/31$295
This American Airlines deal was found by Cheapflights users on 3/30. 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.
土 5/246:43 pmORD - ORF
Nonstop2h 27mAmerican Airlines
日 5/257:00 amORF - ORD
Nonstop2h 23mAmerican Airlines
Deal found 3/30$298
This United Airlines deal was found by Cheapflights users on 3/31. 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.
木 4/246:15 pmORD - ORF
Nonstop2h 19mUnited Airlines
月 4/286:10 amORF - ORD
1 stop4h 36mUnited Airlines
Deal found 3/31$315
This Southwest deal was found by Cheapflights users on 3/30. 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.
土 9/67:30 amORD - ORF
1 stop6h 15mSouthwest
土 9/136:20 amORF - ORD
1 stop6h 30mSouthwest
Deal found 3/30$359

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 3月 31, 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

木 5/8

4:35 pm-10:29 am

1 stop16h 54m

Norfolk

日 5/11

5:02 pm-4:25 pm

2 stops24h 23m

$238

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

土 7/26

6:00 am-4:17 pm

1 stop9h 17m

Norfolk

土 8/2

5:06 pm-11:21 pm

1 stop7h 15m

$240

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

木 4/24

4:30 pm-7:32 pm

1 stop26h 02m

Norfolk

日 4/27

8:56 pm-8:04 am

1 stop12h 08m

$240

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

土 5/24

8:04 am-4:24 pm

1 stop7h 20m

Norfolk

月 5/26

5:12 pm-12:17 am

1 stop8h 05m

$249

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

日 5/25

1:08 pm-5:41 pm

1 stop3h 33m

Norfolk

木 5/29

6:00 am-8:40 am

1 stop3h 40m

$285

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

日 5/25

7:10 am-12:16 pm

1 stop4h 06m

Norfolk

木 5/29

7:40 pm-11:58 pm

1 stop5h 18m

$285

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

水 5/21

6:20 am-1:50 pm

1 stop6h 30m

Norfolk

土 5/24

6:30 pm-7:40 pm

Nonstop2h 10m

$295

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

土 5/24

6:43 pm-10:10 pm

Nonstop2h 27m

Norfolk

日 5/25

7:00 am-8:23 am

Nonstop2h 23m

$298

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

木 4/24

6:15 pm-9:34 pm

Nonstop2h 19m

Norfolk

月 4/28

6:10 am-9:46 am

1 stop4h 36m

$315

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

月 6/2

1:50 pm-6:45 pm

1 stop3h 55m

Norfolk

土 6/7

6:00 am-4:25 pm

2 stops11h 25m

$370

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 23 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 March 28, 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 June is currently the most expensive (average of $372). 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 3月 31, 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 30, 2024.

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 at noon 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 3月 31, 2025.

The most flights from CHI to I1W are scheduled on a Monday (22 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (14 on average).

Rainfall in Isle of Wight by month

Plan your trip to Isle of Wight by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Isle of Wight ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Isle of Wight when rainfall is around 2.9 in.

Temperature in Isle of Wight by month

Plan your trip to Isle of Wight by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Isle of Wight, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 3月 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Chicago to Isle of Wight to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Crew

8.7

Overall

8.0

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Crew

8.7

Overall

8.0

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Crew

8.7

Overall

8.0

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,614 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Crew

8.7

Overall

8.0

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Crew

8.7

Overall

8.0

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.1

Crew

8.7

Overall

8.0

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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?

    $87 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and JetBlue, with prices starting from $99 and $101, 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 GoJet (92%), Air Canada (86%) and Air New Zealand (86%).

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

    The cheapest flight price from Chicago to Isle of Wight is $142. On average you can expect to pay $294. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $199.

  • 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 June is currently the most expensive (average of $372). 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 Chicago to Isle of Wight

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Raleigh flights
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Midway to Reagan-National flights
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O'Hare Intl to Blountville flights
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Evansville to Reagan-National flights
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O'Hare Intl to Salisbury flights
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O'Hare Intl to Newport News flights
Bloomington to Richmond flights
Bloomington to Norfolk flights
Springfield to Reagan-National flights
Midway to Blountville flights
Bloomington to Raleigh flights
Moline to Richmond flights

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 3月 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$215FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$123Average$384FlexibilityNo cancel feeOn-time63%
DeltaCheapest$175Average$485FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$200Average$373FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$207Average$414FlexibilityNo cancel feeOn-time69%
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