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Isle of Wight

$43+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Isle of Wight are usually found in September or October, booked 68 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

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 November 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/233:26 pmORD - ORF
1 stop21h 40mMultiple Airlines
Wed 12/3111:44 amORF - ORD
1 stop11h 40mMultiple Airlines
Deal found 11/17$266
This Mytrip deal was found by Cheapflights users on 11/18. 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.
Sat 12/612:09 pmORD - ORF
3 stops30h 07mSpirit Airlines
Mon 12/88:11 pmORF - ORD
2 stops18h 47mSpirit Airlines
Deal found 11/18$267
This Southwest deal was found by Cheapflights users on 11/20. 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.
Tue 12/96:05 pmMDW - ORF
Nonstop2h 00mSouthwest
Tue 12/165:30 pmORF - MDW
Nonstop2h 10mSouthwest
Deal found 11/20$269
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Tue 12/95:50 pmORD - ORF
Nonstop2h 10mUnited Airlines
Wed 12/241:05 pmORF - ORD
Nonstop2h 34mUnited Airlines
Deal found 11/19$269
This Mytrip deal was found by Cheapflights users on 11/18. 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.
Wed 12/32:01 pmORD - ORF
3 stops28h 15mSpirit Airlines
Sun 12/78:11 pmORF - ORD
2 stops19h 10mSpirit Airlines
Deal found 11/18$270
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Sat 12/209:09 pmORD - ORF
2 stops15h 57mSpirit Airlines
Wed 12/243:01 pmORF - ORD
1 stop10h 29mSpirit Airlines
Deal found 11/19$271
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/217:57 pmORD - ORF
2 stops17h 09mMultiple Airlines
Tue 12/237:40 pmORF - ORD
1 stop15h 38mMultiple Airlines
Deal found 11/19$272
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/236:14 amMDW - ORF
1 stop27h 18mFrontier
Wed 12/3111:44 amORF - MDW
1 stop11h 28mFrontier
Deal found 11/17$273
This American Airlines deal was found by Cheapflights users on 11/20. 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 12/37:04 pmORD - ORF
Nonstop2h 17mAmerican Airlines
Sat 12/62:55 pmORF - ORD
1 stop5h 32mAmerican Airlines
Deal found 11/20$273
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 11/3011:23 amORD - ORF
1 stop21h 20mMultiple Airlines
Wed 12/38:02 pmORF - ORD
1 stop18h 55mMultiple Airlines
Deal found 11/19$275
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Tue 12/94:38 pmORD - ORF
3 stops38h 05mSpirit Airlines
Tue 12/168:11 pmORF - ORD
2 stops17h 28mSpirit Airlines
Deal found 11/20$278
This United Airlines deal was found by Cheapflights users on 11/20. 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.
Tue 12/911:20 amORD - ORF
Nonstop2h 14mUnited Airlines
Tue 12/166:00 amORF - ORD
1 stop5h 44mUnited Airlines
Deal found 11/20$279

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 November 20, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$265
(Kiwi.com)

One-way from

$43
(CheapOair)

Popular in

June

Cheapest in

September

Average price

$409
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. 3% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 20, 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

Tue 12/9

6:05 pm-9:05 pm

Nonstop2h 00m

Norfolk

Tue 12/16

5:30 pm-6:40 pm

Nonstop2h 10m

$269

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 1/16

9:43 am-5:06 pm

1 stop6h 23m

Norfolk

Mon 1/19

11:17 am-10:19 pm

1 stop12h 02m

$269

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 12/9

5:50 pm-9:00 pm

Nonstop2h 10m

Norfolk

Tue 12/16

4:45 pm-6:13 pm

Nonstop2h 28m

$269

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 1/7

7:35 am-3:30 pm

1 stop6h 55m

Norfolk

Wed 1/14

5:35 pm-6:50 pm

Nonstop2h 15m

$273

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 1/7

11:05 am-2:25 pm

Nonstop2h 20m

Norfolk

Wed 1/14

6:30 am-12:05 pm

1 stop6h 35m

$273

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 12/9

6:00 am-11:58 am

1 stop4h 58m

Norfolk

Wed 12/24

1:05 pm-2:39 pm

Nonstop2h 34m

$279

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 12/6

1:16 pm-6:34 pm

1 stop4h 18m

Norfolk

Sat 12/13

1:00 pm-4:22 pm

1 stop4h 22m

$283

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 12/3

1:13 pm-6:34 pm

1 stop4h 21m

Norfolk

Wed 12/10

4:58 pm-8:35 pm

1 stop4h 37m

$283

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 1/7

6:05 am-3:30 pm

1 stop8h 25m

Norfolk

Wed 1/14

4:10 pm-9:50 pm

1 stop6h 40m

$283

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 12/19

7:20 am-6:45 pm

1 stop10h 25m

Norfolk

Mon 12/22

7:40 pm-9:02 am

1 stop14h 22m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 42 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 November 14, 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 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, February is the cheapest month in which you can book a flight from Chicago to Isle of Wight (average of $118). Flying from Chicago to Isle of Wight in January is currently the most expensive (average of $270). 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 November 20, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 19% on flights from Chicago to Isle of Wight by exploring options for tickets in the evening.

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 November 2, 2025.

Travelers seeking maximum savings on their Chicago to Isle of Wight flight should consider departing on Wednesday mornings 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 November 20, 2025.

The most flights from CHI to I1W are scheduled on a Thursday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 November 20, 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
4,249 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

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
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

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
9,029 reviews
Southwest
8.0
Very good
4,249 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

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
11,045 reviews
Southwest
8.0
Very good
4,249 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

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
3,106 reviews
Southwest
8.0
Very good
4,249 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

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?

    Southwest, United Airlines, and Delta can get you from Chicago to Isle of Wight in just under 2h. Your travel time can differ by up to 2h 18m. 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?

    $87 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 $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 Republic Airways (88%), Envoy Air (85%) and United Airlines (82%).

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

    The cheapest flight price from Chicago to Isle of Wight is $115. On average you can expect to pay $349. The most popular route, (Chicago O'Hare Intl - Norfolk), can usually be booked for $146.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Isle of Wight (average of $118). Flying from Chicago to Isle of Wight in January is currently the most expensive (average of $270). 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.
O'Hare Intl to Reagan-National flights
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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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$217Average$424FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$230Average$363FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$237Average$396FlexibilityNo cancel feeOn-time71%

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