$79+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chicago to Isle of Wight with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 Wednesday
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 12, 2025.
Round-trip from | $244 (Southwest) |
|---|---|
One-way from | $79 (Southwest) |
Popular in | June |
Cheapest in | September |
Average price | $422 |
Find flight deals from Chicago to Isle of Wight
Cheapest flights from Chicago to Isle of WightExplore 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 12, 2025.
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 12, 2025.
This Southwest deal was found by Cheapflights users on 6/11. 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.
This FlightHub deal was found by Cheapflights users on 6/12. 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.
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 6/11. 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.
This FlightHub deal was found by Cheapflights users on 6/11. 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.
This Southwest deal was found by Cheapflights users on 6/11. 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.
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight 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 June 12, 2025.
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
MDW - ORF
MDWORF
Chicago Midway
Sat 10/11
1:05 pm-4:05 pm
Nonstop2h 00m
Norfolk
Mon 10/13
6:10 am-1:20 pm
2 stops8h 10m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sat 8/9
7:55 pm-11:22 pm
Nonstop2h 27m
Norfolk
Thu 8/14
6:12 pm-7:50 pm
Nonstop2h 38m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Tue 7/8
7:49 pm-10:35 pm
1 stop25h 46m
Norfolk
Sun 7/13
6:30 pm-3:42 pm
2 stops22h 12m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Wed 7/16
5:05 am-8:15 am
1 stop26h 10m
Norfolk
Sun 7/20
9:05 am-8:55 am
1 stop24h 50m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sat 8/9
6:22 pm-9:40 pm
Nonstop2h 18m
Norfolk
Wed 8/13
6:20 am-7:45 am
Nonstop2h 25m
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 8/21
6:04 am-12:52 pm
1 stop5h 48m
Norfolk
Mon 8/25
5:30 am-9:16 am
1 stop4h 46m
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 7/18
10:31 am-4:25 pm
2 stops28h 54m
Norfolk
Sun 7/20
3:54 pm-9:41 am
2 stops18h 47m
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 9/5
6:15 am-2:27 pm
1 stop7h 12m
Norfolk
Sun 9/7
9:52 am-7:39 am
1 stop22h 47m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sat 7/26
5:20 pm-11:12 pm
1 stop4h 52m
Norfolk
Sat 8/2
6:14 pm-12:09 am
1 stop6h 55m
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sat 8/9
7:30 am-2:45 pm
1 stop6h 15m
Norfolk
Sat 8/16
6:20 am-4:25 pm
2 stops11h 05m
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.
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 9, 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 12, 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 8, 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 12, 2025.
The most flights from CHI to I1W are scheduled on a Thursday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 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 June 12, 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.
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
Boarding
Comfort
Entertainment
Overall
Food
Crew
Reviews
John,May 2025
PVD - BNA
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.
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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.
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 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$79 | Average$245 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$142 | Average$366 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$201 | Average$376 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$238 | Average$382 | FlexibilityNo cancel fee | On-time63% |