$92+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Aug 28 — Sep 41
Round-trip
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 January, booked 61 days in advance, depart on a Saturday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Isle of Wight
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Best
Last-minute
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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 July 29, 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 July 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 9/126:25 am
MDW
- ORF
1 stop8h 25m
Frontier
Sat 9/194:45 pm
ORF
- MDW
1 stop26h 01m
Frontier
Deal found 7/29![Frontier logo]()
$277
This Frontier deal was found by Cheapflights users on 7/25. 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.
Fri 10/236:05 am
ORD
- ORF
1 stop10h 25m
Frontier
Sun 10/2512:57 pm
ORF
- ORD
1 stop8h 31m
Frontier
Deal found 7/25![Frontier logo]()
$280
This Priceline deal was found by Cheapflights users on 7/24. 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.
Fri 8/216:05 am
ORD
- ORF
1 stop9h 06m
Frontier
Sun 8/235:06 pm
ORF
- ORD
1 stop7h 02m
Frontier
Deal found 7/24![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 11/127:25 am
MDW
- ORF
2 stops12h 20m
Multiple Airlines
Mon 11/1612:57 pm
ORF
- MDW
1 stop23h 01m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 9/38:30 pm
ORD
- ORF
2 stops14h 55m
Frontier
Sun 9/61:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Deal found 7/26![Frontier logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/216:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Sun 8/231:20 pm
ORF
- MDW
1 stop22h 35m
Frontier
Deal found 7/27![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/141:50 pm
ORD
- ORF
1 stop20h 31m
Frontier
Mon 8/1712:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Deal found 7/25![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/208:05 am
ORD
- ORF
2 stops14h 48m
Multiple Airlines
Sun 8/231:20 pm
ORF
- ORD
1 stop19h 33m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:25 am
MDW
- ORF
1 stop27h 37m
Frontier
Mon 11/212:57 pm
ORF
- MDW
1 stop9h 56m
Frontier
Deal found 7/25![Frontier logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:03 pm
MDW
- ORF
1 stop22h 59m
Frontier
Sat 10/2412:57 pm
ORF
- MDW
1 stop10h 01m
Frontier
Deal found 7/25![Frontier logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:46 pm
ORD
- ORF
2 stops20h 16m
Frontier
Thu 11/1912:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Deal found 7/25![Frontier logo]()
$286
This CheapOair deal was found by Cheapflights users on 7/28. 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.
Thu 8/207:44 pm
ORD
- ORF
1 stop19h 27m
Frontier
Sun 8/235:06 pm
ORF
- ORD
1 stop7h 02m
Frontier
Deal found 7/28![Frontier logo]()
$287
Best flights from Chicago to Isle of WightDiscover carefully curated flight deals from Chicago to Isle of Wight that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 29, 2026.
Discover carefully curated flight deals from Chicago to Isle of Wight that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 29, 2026.
This Southwest deal was found by Cheapflights users on 7/27. 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.
Thu 8/206:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Mon 8/248:00 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/27![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Mon 8/247:30 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Mon 8/316:00 am
ORF
- ORD
Nonstop2h 34m
United Airlines
Deal found 7/28![United Airlines logo]()
$317
This CheapOair deal was found by Cheapflights users on 7/24. 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.
Fri 9/49:10 pm
ORD
- ORF
1 stop18h 01m
Multiple Airlines
Thu 9/107:27 pm
ORF
- ORD
2 stops15h 31m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 7/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:45 am
ORD
- ORF
Nonstop2h 19m
American Airlines
Mon 8/1710:40 am
ORF
- ORD
1 stop6h 20m
American Airlines
Deal found 7/24![American Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 7/26. 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.
Wed 9/96:25 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Wed 9/168:05 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/26![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 7/26. 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.
Thu 9/310:55 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Sun 9/612:34 pm
ORF
- ORD
Nonstop2h 29m
United Airlines
Deal found 7/26![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 7/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:45 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Mon 11/27:30 am
ORF
- MDW
Nonstop2h 15m
Southwest
Deal found 7/25![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 7/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:15 pm
ORD
- ORF
1 stop4h 28m
United Airlines
Wed 9/165:02 pm
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 7/24![United Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/26. 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.
Fri 9/47:30 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Sun 9/612:34 pm
ORF
- ORD
Nonstop2h 29m
United Airlines
Deal found 7/26![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 7/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Thu 9/310:10 am
ORF
- MDW
1 stop7h 05m
Southwest
Deal found 7/25![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 7/26. 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.
Thu 1/76:15 pm
ORD
- ORF
Nonstop2h 17m
United Airlines
Sun 1/176:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 7/26![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sat 9/125:00 am
MDW
- ORF
2 stops9h 00m
Southwest
Sat 9/199:55 am
ORF
- MDW
2 stops8h 10m
Southwest
Deal found 7/29![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 7/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:00 am
MDW
- ORF
1 stop5h 35m
Southwest
Mon 10/57:45 am
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 7/25![Southwest logo]()
$348
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Thu 12/316:07 pm
ORD
- ORF
1 stop4h 09m
United Airlines
Sat 1/27:50 pm
ORF
- ORD
1 stop4h 32m
United Airlines
Deal found 7/29![United Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 7/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:15 pm
ORD
- ORF
Nonstop2h 33m
United Airlines
Wed 8/196:15 am
ORF
- ORD
1 stop6h 38m
United Airlines
Deal found 7/25![United Airlines logo]()
$407
Last-minute flights from Chicago to Isle of WightDiscover last-minute flight deals from Chicago to Isle of Wight. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Isle of Wight. Data last updated July 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Thu 8/138:52 pm
ORD
- ORF
2 stops37h 29m
Frontier
Mon 8/1712:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Deal found 7/24![Frontier logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/141:50 pm
ORD
- ORF
1 stop20h 31m
Frontier
Mon 8/1712:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Deal found 7/25![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/151:50 pm
ORD
- ORF
1 stop20h 25m
Frontier
Wed 8/191:20 pm
ORF
- ORD
1 stop7h 48m
Frontier
Deal found 7/27![Frontier logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/208:05 am
ORD
- ORF
2 stops14h 48m
Multiple Airlines
Sun 8/231:20 pm
ORF
- ORD
1 stop19h 33m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$284
This CheapOair deal was found by Cheapflights users on 7/28. 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.
Thu 8/207:44 pm
ORD
- ORF
1 stop19h 27m
Frontier
Sun 8/235:06 pm
ORF
- ORD
1 stop7h 02m
Frontier
Deal found 7/28![Frontier logo]()
$287
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 8/209:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Mon 8/248:00 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/29![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/206:05 am
MDW
- ORF
1 stop5h 20m
Multiple Airlines
Mon 8/2412:04 pm
ORF
- MDW
2 stops11h 43m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$334
This Priceline deal was found by Cheapflights users on 7/24. 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.
Fri 8/216:05 am
ORD
- ORF
1 stop9h 06m
Frontier
Sun 8/235:06 pm
ORF
- ORD
1 stop7h 02m
Frontier
Deal found 7/24![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/216:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Sun 8/231:20 pm
ORF
- MDW
1 stop22h 35m
Frontier
Deal found 7/27![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/277:44 pm
ORD
- ORF
2 stops39h 41m
Frontier
Thu 9/31:20 pm
ORF
- ORD
1 stop7h 44m
Frontier
Deal found 7/28![Frontier logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/279:26 pm
MDW
- ORF
2 stops37h 59m
Frontier
Thu 9/31:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/28![Frontier logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/287:05 am
ORD
- ORF
2 stops15h 03m
Multiple Airlines
Sun 8/301:20 pm
ORF
- ORD
1 stop19h 33m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$307
One-way flights from Chicago to Isle of WightSearch for one-way flight options from Chicago to Isle of Wight. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
Search for one-way flight options from Chicago to Isle of Wight. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:05 am
ORD
- ORF
2 stops9h 21m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/251:59 pm
ORD
- ORF
1 stop21h 26m
Frontier
Deal found 7/28![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:11 am
ORD
- ORF
2 stops27h 48m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/307:05 am
ORD
- ORF
1 stop28h 20m
Frontier
Deal found 7/28![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/267:05 am
ORD
- ORF
1 stop28h 20m
Frontier
Deal found 7/28![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 9/287:11 am
ORD
- ORF
2 stops27h 48m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 10/269:33 pm
ORD
- ORF
1 stop13h 29m
Frontier
Deal found 7/29![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/176:05 am
MDW
- ORF
1 stop29h 20m
Frontier
Deal found 7/28![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/297:11 am
ORD
- ORF
1 stop28h 14m
Frontier
Deal found 7/26![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 8/256:05 am
MDW
- ORF
1 stop29h 20m
Frontier
Deal found 7/29![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 7/25. 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.
Thu 8/276:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/25![Frontier logo]()
$123
This iWofly deal was found by Cheapflights users on 7/24. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/24![Frontier logo]()
$124
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 July 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $280 (Frontier) |
One-way from | $92 (Kiwi.com) |
Popular in | March |
Cheapest in | December |
Average price | $443 |
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 July 29, 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
Cheapest round-trip
Quickest round-trip
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 8/20
6:50 pm-9:55 pm
Nonstop2h 05m
Norfolk
Mon 8/24
8:00 am-9:00 am
Nonstop2h 00m
$317
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Mon 8/24
7:30 am-11:00 am
Nonstop2h 30m
Norfolk
Mon 8/31
6:00 am-7:34 am
Nonstop2h 34m
$317
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 9/9
6:25 pm-9:35 pm
Nonstop2h 10m
Norfolk
Wed 9/16
8:05 am-9:05 am
Nonstop2h 00m
$317
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Thu 9/3
10:55 am-2:17 pm
Nonstop2h 22m
Norfolk
Sun 9/6
12:34 pm-2:03 pm
Nonstop2h 29m
$322
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 10/30
6:45 pm-9:45 pm
Nonstop2h 00m
Norfolk
Mon 11/2
7:30 am-8:45 am
Nonstop2h 15m
$322
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Wed 9/9
6:15 pm-11:43 pm
1 stop4h 28m
Norfolk
Wed 9/16
5:02 pm-6:30 pm
Nonstop2h 28m
$327
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Fri 9/4
7:30 am-11:00 am
Nonstop2h 30m
Norfolk
Sun 9/6
12:34 pm-2:03 pm
Nonstop2h 29m
$343
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Thu 1/7
6:15 pm-9:32 pm
Nonstop2h 17m
Norfolk
Sun 1/17
6:00 am-7:28 am
Nonstop2h 28m
$345
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 8/27
9:00 am-12:10 pm
Nonstop2h 10m
Norfolk
Thu 9/3
10:10 am-4:15 pm
1 stop7h 05m
$347
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 9/12
5:00 am-3:00 pm
2 stops9h 00m
Norfolk
Sat 9/19
9:55 am-5:05 pm
2 stops8h 10m
$347
Showing 1-10 of 36 resultsSorted by cheapest first
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.
ORD-ORF
MDW-ORF
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
CHI-I1W
ORD-ORF
MDW-ORF
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 July 29, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 5% on flights from Chicago to Isle of Wight by exploring options for tickets in the morning.
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 July 29, 2026.
The most flights from CHI to I1W are scheduled on a Monday (26 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (15 on average).
How much does it cost to fly round-trip from Chicago to Isle of Wight?
Airfare is typical for this route at the moment.
Chicago to Isle of Wight flights typically cost between $277 and $520 in October.The cheapest round-trip price found within the last 5 days was $280 on Frontier (Oct 23-Oct 25).
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 July 25, 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. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 July 29, 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.
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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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Complete your trip
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Chicago and Isle of Wight flights
Browse other Chicago and Isle of Wight flight options. Last updated on July 29, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on July 29, 2026.
Popular flight searches
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Chicago to Isle of Wight flights
Consider these flights traveling from Chicago to Isle of Wight.
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 July 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$102 | Average$267 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$174 | Average$383 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$219 | Average$411 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$453 | FlexibilityNo cancel fee | On-time71% |