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Isle of Wight

$63+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Mrz 30 — Apr 61
Mo 3/30
Mo 4/6
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 70 days in advance, depart on a Wednesday or Tuesday 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 Februar 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/24. 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.
Do 4/233:15 pm
ORD
-
ORF
1 stop18h 02m
Multiple Airlines
Sa 4/2511:27 am
ORF
-
ORD
1 stop8h 27m
Multiple Airlines
Deal found 2/24$145
This Priceline deal was found by Cheapflights users on 2/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 4/179:14 am
MDW
-
ORF
1 stop7h 13m
Frontier
So 4/1911:27 am
ORF
-
MDW
1 stop9h 04m
Frontier
Deal found 2/24$160
This Frontier deal was found by Cheapflights users on 2/25. 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.
Sa 4/258:00 am
ORD
-
ORF
1 stop9h 21m
Frontier
Mo 4/2711:27 am
ORF
-
ORD
1 stop12h 12m
Frontier
Deal found 2/25$160
This Kiwi.com deal was found by Cheapflights users on 2/24. 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.
Mi 4/152:15 pm
MDW
-
ORF
1 stop19h 17m
Frontier
Mo 4/2011:27 am
ORF
-
MDW
1 stop9h 04m
Frontier
Deal found 2/24$166
This Kiwi.com deal was found by Cheapflights users on 2/24. 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.
Do 5/72:20 pm
MDW
-
ORF
1 stop19h 04m
Frontier
Mo 5/1111:19 am
ORF
-
MDW
1 stop9h 12m
Frontier
Deal found 2/24$172
This Expedia deal was found by Cheapflights users on 2/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 4/176:04 pm
ORD
-
ORF
1 stop23h 17m
Frontier
So 4/1912:32 pm
ORF
-
ORD
1 stop12h 27m
Frontier
Deal found 2/24$181
This CheapOair deal was found by Cheapflights users on 2/25. 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.
Fr 4/176:04 pm
ORD
-
ORF
1 stop23h 17m
Frontier
Mo 4/2011:27 am
ORF
-
ORD
1 stop12h 12m
Frontier
Deal found 2/25$192
This CheapOair deal was found by Cheapflights users on 2/24. 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.
Fr 4/173:31 pm
ORD
-
ORF
1 stop6h 27m
Multiple Airlines
Sa 4/1811:27 am
ORF
-
ORD
1 stop12h 12m
Multiple Airlines
Deal found 2/24$193
This Frontier deal was found by Cheapflights users on 2/24. 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.
Fr 5/89:14 am
MDW
-
ORF
1 stop7h 35m
Frontier
So 5/1011:19 am
ORF
-
MDW
1 stop12h 00m
Frontier
Deal found 2/24$202
This Frontier deal was found by Cheapflights users on 2/25. 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.
Fr 5/86:57 am
ORD
-
ORF
1 stop9h 52m
Frontier
So 5/1011:19 am
ORF
-
ORD
1 stop12h 20m
Frontier
Deal found 2/25$202
This Mytrip deal was found by Cheapflights users on 2/24. 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.
Di 3/107:00 am
ORD
-
ORF
1 stop10h 26m
Spirit Airlines
Di 3/318:41 pm
ORF
-
ORD
2 stops16h 09m
Spirit Airlines
Deal found 2/24$206
This Kiwi.com deal was found by Cheapflights users on 2/24. 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.
Do 4/237:30 am
MDW
-
ORF
2 stops14h 28m
Multiple Airlines
Sa 4/2511:27 am
ORF
-
MDW
1 stop8h 10m
Multiple Airlines
Deal found 2/24$207

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 Februar 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$145
(Kiwi.com)

One-way from

$63
(Kiwi.com)

Popular in

April

Cheapest in

December

Average price

$361
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. 6% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 Februar 28, 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

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mi 4/15

5:48 pm-9:08 pm

Nonstop2h 20m

Norfolk

Mo 4/20

5:00 pm-6:31 pm

Nonstop2h 31m

$252

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fr 4/10

11:00 am-2:20 pm

Nonstop2h 20m

Norfolk

Mo 4/13

6:11 am-11:51 am

1 stop6h 40m

$265

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mi 4/15

8:00 am-5:50 pm

2 stops8h 50m

Norfolk

Mo 4/20

2:30 pm-8:35 pm

2 stops7h 05m

$289

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sa 5/2

1:55 pm-11:05 pm

2 stops8h 10m

Norfolk

Sa 5/9

6:10 am-3:30 pm

2 stops10h 20m

$295

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fr 4/3

11:00 am-2:20 pm

Nonstop2h 20m

Norfolk

Di 4/7

6:04 am-10:43 am

1 stop5h 39m

$300

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sa 3/28

5:45 pm-8:54 pm

Nonstop2h 09m

Norfolk

Di 3/31

10:27 am-4:49 pm

1 stop7h 22m

$303

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sa 8/1

6:00 am-6:00 pm

1 stop11h 00m

Norfolk

Sa 8/8

1:25 pm-9:20 pm

1 stop8h 55m

$320

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Mo 6/22

12:22 pm-3:43 pm

Nonstop2h 21m

Norfolk

Fr 6/26

8:00 am-9:32 am

Nonstop2h 32m

$334

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fr 3/27

5:45 pm-8:54 pm

Nonstop2h 09m

Norfolk

Mi 4/1

10:15 am-11:46 am

Nonstop2h 31m

$340

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sa 5/23

5:25 pm-11:05 pm

1 stop4h 40m

Norfolk

Sa 5/30

7:00 pm-10:35 pm

1 stop4h 35m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/24

Showing 1-10 of 39 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

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 February 20, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to Isle of Wight, you should look to book at least 68 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 $130). Flying from Chicago to Isle of Wight in December is currently the most expensive (average of $265). 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 Februar 28, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 14% 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 February 21, 2026.

Travelers seeking maximum savings on their Chicago to Isle of Wight flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday 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 Februar 28, 2026.

The most flights from CHI to I1W are scheduled on a Friday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 Februar 28, 2026.
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
4,303 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Southwest
8.0
Very good
4,303 reviews
Southwest
8.0
Very good
4,303 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
United Airlines
7.4
Good
9,362 reviews
Southwest
8.0
Very good
4,303 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
American Airlines
7.2
Good
11,367 reviews
Southwest
8.0
Very good
4,303 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Frontier
5.7
Fair
3,041 reviews
Southwest
8.0
Very good
4,303 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

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 20m. Your travel time can differ by up to 6h 30m. 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?

    $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 $132, 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 Envoy Air (83%), GoJet (81%) and Republic Airways (81%).

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

    The cheapest flight price from Chicago to Isle of Wight is $148. On average you can expect to pay $345. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $160.

  • 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 $130). Flying from Chicago to Isle of Wight in December is currently the most expensive (average of $265). 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.
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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 Februar 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$245FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$174Average$366FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$207Average$391FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$237Average$394FlexibilityNo cancel feeOn-time71%

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