$44+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Feb 4 — Feb 111
1 adult, Economy
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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 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 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 January 5, 2026.
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 January 5, 2026.
This Expedia deal was found by Cheapflights users on 1/4. 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.
Fri 1/237:20 amORD - ORF
1 stop10h 18mMultiple Airlines
Mon 1/2611:43 amORF - ORD
1 stop12h 03mMultiple Airlines
Deal found 1/4![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 2/37:20 amORD - ORF
1 stop10h 18mMultiple Airlines
Tue 2/101:02 pmORF - ORD
1 stop27h 50mMultiple Airlines
Deal found 1/4![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 1/235:15 amORD - ORF
1 stop12h 23mMultiple Airlines
Fri 1/307:33 pmORF - ORD
1 stop25h 11mMultiple Airlines
Deal found 1/2![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 1/249:25 amORD - ORF
1 stop9h 50mMultiple Airlines
Fri 1/307:33 pmORF - ORD
1 stop25h 11mMultiple Airlines
Deal found 1/2![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 1/3. 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 2/1910:44 amORD - ORF
1 stop6h 44mMultiple Airlines
Sun 2/227:31 pmORF - ORD
1 stop16h 51mMultiple Airlines
Deal found 1/3![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 1/253:05 pmORD - ORF
1 stop26h 33mMultiple Airlines
Fri 1/307:33 pmORF - ORD
1 stop25h 11mMultiple Airlines
Deal found 1/2![Multiple Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 1/235:15 amORD - ORF
1 stop12h 23mMultiple Airlines
Sat 1/316:45 amORF - ORD
1 stop10h 55mMultiple Airlines
Deal found 1/2![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 1/249:25 amORD - ORF
1 stop9h 50mMultiple Airlines
Sat 1/316:45 amORF - ORD
1 stop10h 55mMultiple Airlines
Deal found 1/2![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 1/3. 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 2/238:16 pmORD - ORF
1 stop21h 10mMultiple Airlines
Fri 2/276:45 amORF - ORD
2 stops17h 39mMultiple Airlines
Deal found 1/3![Multiple Airlines logo]()
$150
This CheapOair deal was found by Cheapflights users on 1/4. 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.
Fri 1/235:15 amORD - ORF
1 stop12h 23mSpirit Airlines
Mon 1/266:45 amORF - ORD
1 stop12h 07mSpirit Airlines
Deal found 1/4![Spirit Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 1/231:00 pmMDW - ORF
1 stop7h 50mMultiple Airlines
Mon 1/266:45 amORF - MDW
1 stop14h 13mMultiple Airlines
Deal found 1/2![Multiple Airlines logo]()
$190
This Frontier deal was found by Cheapflights users on 1/3. 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.
Thu 2/197:30 amMDW - ORF
1 stop9h 58mFrontier
Sun 2/2211:32 amORF - MDW
1 stop9h 27mFrontier
Deal found 1/3![Frontier logo]()
$195
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 January 5, 2026.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $112 (Expedia) |
One-way from | $44 (Expedia) |
Popular in | April |
Cheapest in | December |
Average price | $413 |
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 January 5, 2026.
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
Mon 2/23
8:16 pm-6:26 pm
1 stop21h 10m
Norfolk
Fri 2/27
7:31 pm-7:50 pm
1 stop25h 19m
$133
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Tue 2/3
5:32 pm-5:20 pm
2 stops22h 48m
Norfolk
Tue 2/10
1:02 pm-3:52 pm
1 stop27h 50m
$154
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sun 1/25
8:43 pm-6:38 pm
1 stop20h 55m
Norfolk
Sat 1/31
6:45 am-4:40 pm
1 stop10h 55m
$158
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 1/23
1:00 pm-9:50 pm
1 stop7h 50m
Norfolk
Mon 1/26
6:45 am-7:58 pm
1 stop14h 13m
$190
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Sat 1/17
1:55 pm-5:06 pm
Nonstop2h 11m
Norfolk
Tue 1/20
4:45 pm-6:19 pm
Nonstop2h 34m
$235
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 2/14
6:05 pm-9:05 pm
Nonstop2h 00m
Norfolk
Tue 2/17
6:20 am-12:05 pm
1 stop6h 45m
$239
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Tue 2/3
5:30 pm-8:30 pm
Nonstop2h 00m
Norfolk
Tue 2/10
5:35 pm-6:50 pm
Nonstop2h 15m
$263
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Tue 2/3
11:12 am-2:32 pm
Nonstop2h 20m
Norfolk
Tue 2/10
4:45 pm-6:19 pm
Nonstop2h 34m
$263
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 3/25
6:05 pm-9:05 pm
Nonstop2h 00m
Norfolk
Wed 4/1
6:30 pm-7:50 pm
Nonstop2h 20m
$282
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Tue 3/24
6:05 pm-9:05 pm
Nonstop2h 00m
Norfolk
Tue 3/31
6:30 pm-7:50 pm
Nonstop2h 20m
$282
Showing 1-10 of 37 results
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 January 2, 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, February is the cheapest month in which you can book a flight from Chicago to Isle of Wight (average of $123). 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 January 5, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 12% 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 January 3, 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. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 January 5, 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.
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 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 January 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$224 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$207 | Average$400 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$213 | Average$372 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$233 | Average$394 | FlexibilityNo cancel fee | On-time71% |