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Isle of Wight

$69+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Jun 10 — Jun 171
Wed 6/10
Wed 6/17
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Isle of Wight are usually found in December or September, booked 61 days in advance, depart on a Wednesday or Saturday and return on a Thursday

Cheap 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 May 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:00 am
MDW
-
ORF
1 stop28h 26m
Frontier
Sat 6/2712:06 pm
ORF
-
MDW
1 stop11h 05m
Frontier
Deal found 5/9$307
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Mon 6/16:55 am
ORD
-
ORF
1 stop27h 16m
Frontier
Fri 6/512:06 pm
ORF
-
ORD
1 stop8h 23m
Frontier
Deal found 5/10$307
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 5/2712:04 pm
MDW
-
ORF
2 stops9h 38m
Multiple Airlines
Sat 6/612:00 pm
ORF
-
MDW
1 stop11h 02m
Multiple Airlines
Deal found 5/10$309
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 7/129:57 pm
ORD
-
ORF
2 stops36h 24m
Frontier
Sun 7/1912:21 pm
ORF
-
ORD
1 stop20h 32m
Frontier
Deal found 5/7$310
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Fri 6/266:00 am
MDW
-
ORF
1 stop28h 21m
Frontier
Tue 6/307:25 pm
ORF
-
MDW
2 stops16h 44m
Frontier
Deal found 5/6$313
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 5/281:50 pm
ORD
-
ORF
1 stop20h 21m
Frontier
Sat 5/3012:00 pm
ORF
-
ORD
2 stops12h 13m
Frontier
Deal found 5/8$313
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 5/266:00 am
MDW
-
ORF
1 stop28h 11m
Frontier
Thu 5/2812:06 pm
ORF
-
MDW
1 stop24h 03m
Frontier
Deal found 5/6$314
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:50 pm
ORD
-
ORF
1 stop20h 21m
Frontier
Mon 6/112:06 pm
ORF
-
ORD
2 stops25h 18m
Frontier
Deal found 5/9$314
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Sat 7/2512:11 pm
MDW
-
ORF
1 stop22h 10m
Frontier
Fri 7/319:35 pm
ORF
-
MDW
2 stops25h 33m
Frontier
Deal found 5/7$315
This CheapOair deal was found by Cheapflights users on 5/8. 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.
Wed 5/275:11 pm
ORD
-
ORF
1 stop26h 06m
Frontier
Sat 5/3012:00 pm
ORF
-
ORD
1 stop8h 41m
Frontier
Deal found 5/8$315
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 6/146:00 am
MDW
-
ORF
1 stop28h 26m
Frontier
Sun 6/2112:21 pm
ORF
-
MDW
1 stop23h 48m
Frontier
Deal found 5/7$316
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Sun 6/76:55 am
ORD
-
ORF
1 stop27h 16m
Frontier
Sun 6/1412:21 pm
ORF
-
ORD
1 stop20h 42m
Frontier
Deal found 5/10$317

Find 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 May 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$307
(Kiwi.com)

One-way from

$69
(Kiwi.com)

Popular in

March

Cheapest in

December

Average price

$393
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Norfolk flights.
Search Deals
From Chicago (CHI) to Isle of Wight
Search Deals
One-way flight from Chicago (CHI) to Isle of Wight
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 11, 2026.
Use the filters below to find and compare flights from Chicago to Isle of Wight that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 6/16

6:45 am-10:07 am

Nonstop2h 22m

Norfolk

Wed 6/24

8:00 am-9:32 am

Nonstop2h 32m

$337

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 6/2

9:29 pm-12:57 am

Nonstop2h 28m

Norfolk

Tue 6/9

10:48 am-12:27 pm

Nonstop2h 39m

$337
Quickest round-trip

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sun 6/14

7:00 pm-10:00 pm

Nonstop2h 00m

Norfolk

Wed 6/17

11:40 am-12:45 pm

Nonstop2h 05m

$350

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 7/7

6:45 am-10:07 am

Nonstop2h 22m

Norfolk

Sun 7/12

6:00 am-7:28 am

Nonstop2h 28m

$350

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 6/2

7:07 am-12:58 pm

1 stop4h 51m

Norfolk

Wed 6/3

4:39 pm-9:53 pm

1 stop6h 14m

$357

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 8/5

6:25 pm-9:30 pm

Nonstop2h 05m

Norfolk

Sun 8/9

6:25 pm-9:55 pm

1 stop4h 30m

$360

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 7/1

7:55 am-11:05 am

Nonstop2h 10m

Norfolk

Sun 7/5

6:15 pm-11:40 pm

1 stop6h 25m

$360

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 10/30

7:55 am-11:05 am

Nonstop2h 10m

Norfolk

Sun 11/1

7:30 am-8:45 am

Nonstop2h 15m

$363

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 9/18

2:00 pm-5:18 pm

Nonstop2h 18m

Norfolk

Sun 9/20

8:10 am-9:42 am

Nonstop2h 32m

$363

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 10/30

9:30 pm-12:52 am

Nonstop2h 22m

Norfolk

Sun 11/1

11:36 am-1:15 pm

Nonstop2h 39m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

Showing 1-10 of 40 resultsSorted by cheapest first
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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

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 May 11, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 6% on flights from Chicago to Isle of Wight by exploring options for tickets in the morning.

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 May 9, 2026.

Travelers seeking maximum savings on their Chicago to Isle of Wight flight should consider departing on Sunday mornings when fares are most often at their lowest. Monday afternoons 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 May 11, 2026.

The most flights from CHI to I1W are scheduled on a Monday (27 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (24 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 May 11, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican 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
4,296 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,296 reviews
Southwest
8.0
Very good
4,296 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,701 reviews
Southwest
8.0
Very good
4,296 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,664 reviews
Southwest
8.0
Very good
4,296 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,951 reviews
Southwest
8.0
Very good
4,296 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 Delta can get you from Chicago to Isle of Wight in just under 2h. Your travel time can differ by up to 2h 51m. The distance from Chicago to Isle of Wight is about 702 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?

    $93 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $130 and $133, 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 (83%), United Airlines (74%) and Air Canada (74%).

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

    The cheapest flight price from Chicago to Isle of Wight is $118. On average you can expect to pay $350. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $213.

  • 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.

See more FAQs

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Top 4 airlines flying from Chicago to Isle of Wight

Discover the top 4 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 May 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$265FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$174Average$354FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$217Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$426FlexibilityNo cancel feeOn-time71%

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