$90+ Cheap flights from Chicago (CHI) to Isle of Wight, VA
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Oct 22 — Oct 291
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 58 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
Cheap flight deals from Chicago to Isle of Wight
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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 September 22, 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 September 22, 2026.
This Priceline deal was found by Cheapflights users on 9/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:55 am -
1 stop9h 54m
Tue 11/246:24 pm -
1 stop7h 18m
Deal found 9/20![Frontier logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Wed 10/217:44 pm -
1 stop15h 54m
Mon 10/263:48 pm -
2 stops27h 57m
Deal found 9/19![Frontier logo]()
$300
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/52:32 pm -
Nonstop2h 29m
Sat 10/106:29 pm -
Nonstop2h 51m
Deal found 9/17![American Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:00 am -
2 stops13h 43m
Sun 11/81:31 pm -
1 stop20h 46m
Deal found 9/18![Multiple Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/118:03 pm -
Nonstop2h 26m
Sat 1/912:11 pm -
Nonstop2h 48m
Deal found 9/17![American Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:09 pm -
1 stop6h 36m
Mon 11/25:25 pm -
1 stop6h 08m
Deal found 9/17![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/52:29 pm -
1 stop6h 57m
Sat 10/105:25 pm -
1 stop7h 32m
Deal found 9/17![Delta logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 11/196:16 am -
1 stop5h 30m
Sat 11/217:34 pm -
1 stop18h 59m
Deal found 9/21![Frontier logo]()
$305
This Frontier deal was found by Cheapflights users on 9/21. 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.
Sat 11/77:15 am -
1 stop6h 39m
Sun 11/151:31 pm -
1 stop6h 14m
Deal found 9/21![Frontier logo]()
$305
This Mytrip deal was found by Cheapflights users on 9/19. 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.
Wed 10/148:04 am -
2 stops27h 34m
Sat 10/173:50 pm -
2 stops20h 31m
Deal found 9/19![Frontier logo]()
$306
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:46 pm -
2 stops23h 02m
Thu 10/81:39 pm -
1 stop11h 04m
Deal found 9/17![Frontier logo]()
$307
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:45 am -
Nonstop2h 30m
Thu 10/86:15 am -
1 stop6h 33m
Deal found 9/17![United Airlines logo]()
$307
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 September 22, 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 September 22, 2026.
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:09 pm -
1 stop6h 36m
Mon 11/25:25 pm -
1 stop6h 08m
Deal found 9/17![Delta logo]()
$304
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:45 am -
Nonstop2h 30m
Thu 10/86:15 am -
1 stop6h 33m
Deal found 9/17![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 9/21. 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 11/186:25 pm -
Nonstop2h 05m
Sat 11/217:15 pm -
Nonstop2h 15m
Deal found 9/21![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:29 pm -
1 stop5h 03m
Mon 11/23:13 pm -
1 stop4h 58m
Deal found 9/17![Delta logo]()
$304
This United Airlines deal was found by Cheapflights users on 9/21. 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 12/246:10 pm -
1 stop4h 20m
Wed 12/306:00 am -
Nonstop2h 45m
Deal found 9/21![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:40 pm -
1 stop5h 50m
Mon 10/127:00 pm -
Nonstop2h 10m
Deal found 9/19![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 9/20. 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.
Fri 10/168:45 am -
Nonstop2h 30m
Mon 10/195:01 pm -
Nonstop2h 29m
Deal found 9/20![United Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:20 pm -
2 stops6h 55m
Mon 11/233:25 pm -
2 stops8h 20m
Deal found 9/19![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:25 pm -
Nonstop2h 05m
Sun 11/227:30 am -
Nonstop2h 15m
Deal found 9/19![Southwest logo]()
$365
This Southwest deal was found by Cheapflights users on 9/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:25 am -
1 stop5h 10m
Mon 10/195:50 pm -
1 stop7h 05m
Deal found 9/18![Southwest logo]()
$371
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2011:57 am -
Nonstop2h 19m
Thu 10/226:15 am -
1 stop6h 31m
Deal found 9/18![United Airlines logo]()
$419
This Southwest deal was found by Cheapflights users on 9/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:10 pm -
Nonstop2h 05m
Tue 12/13:05 pm -
2 stops5h 40m
Deal found 9/19![Southwest logo]()
$380
This KAYAK deal was found by Cheapflights users on 9/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:51 pm -
1 stop7h 32m
Wed 10/712:00 pm -
1 stop6h 20m
Deal found 9/21![Delta logo]()
$518
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:10 pm -
2 stops14h 56m
Sat 1/98:00 pm -
1 stop4h 59m
Deal found 9/17![United Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 9/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:20 pm -
2 stops6h 20m
Sun 11/13:30 pm -
2 stops6h 00m
Deal found 9/17![Southwest logo]()
$405
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:57 am -
Nonstop2h 19m
Sat 10/106:20 am -
Nonstop2h 33m
Deal found 9/18![United Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 9/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:20 pm -
2 stops6h 20m
Sun 10/257:55 pm -
1 stop5h 15m
Deal found 9/17![Southwest logo]()
$416
This United Airlines deal was found by Cheapflights users on 9/21. 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 10/158:45 am -
Nonstop2h 30m
Sun 10/186:20 am -
Nonstop2h 33m
Deal found 9/21![United Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:50 pm -
2 stops17h 22m
Mon 11/26:15 am -
1 stop4h 30m
Deal found 9/17![United Airlines logo]()
$492
Last-minute flights from Chicago to Isle of WightDiscover last-minute flight deals from Chicago to Isle of Wight. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Isle of Wight. Data last updated September 22, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/52:32 pm -
Nonstop2h 29m
Sat 10/106:29 pm -
Nonstop2h 51m
Deal found 9/17![American Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/52:29 pm -
1 stop6h 57m
Sat 10/105:25 pm -
1 stop7h 32m
Deal found 9/17![Delta logo]()
$304
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:46 pm -
2 stops23h 02m
Thu 10/81:39 pm -
1 stop11h 04m
Deal found 9/17![Frontier logo]()
$307
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:45 am -
Nonstop2h 30m
Thu 10/86:15 am -
1 stop6h 33m
Deal found 9/17![United Airlines logo]()
$307
This Frontier deal was found by Cheapflights users on 9/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:21 am -
1 stop5h 23m
Sun 10/111:19 pm -
1 stop5h 26m
Deal found 9/17![Frontier logo]()
$310
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:59 pm -
Nonstop2h 27m
Tue 10/137:01 am -
Nonstop2h 39m
Deal found 9/17![American Airlines logo]()
$303
This Mytrip deal was found by Cheapflights users on 9/19. 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.
Wed 10/148:04 am -
2 stops27h 34m
Sat 10/173:50 pm -
2 stops20h 31m
Deal found 9/19![Frontier logo]()
$306
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:40 am -
2 stops27h 58m
Sun 10/181:19 pm -
2 stops19h 12m
Deal found 9/17![Frontier logo]()
$312
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:45 am -
Nonstop2h 30m
Mon 10/196:20 am -
Nonstop2h 33m
Deal found 9/17![United Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Wed 10/217:44 pm -
1 stop15h 54m
Mon 10/263:48 pm -
2 stops27h 57m
Deal found 9/19![Frontier logo]()
$300
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:09 pm -
1 stop6h 36m
Mon 11/25:25 pm -
1 stop6h 08m
Deal found 9/17![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 9/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:00 am -
Nonstop2h 00m
Mon 11/29:55 am -
2 stops9h 25m
Deal found 9/17![Southwest logo]()
$312
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 September 22, 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 September 22, 2026.
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:15 am -
1 stop6h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$90
This Priceline deal was found by Cheapflights users on 9/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:15 am -
1 stop9h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/206:00 am -
1 stop5h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 12/168:15 am -
1 stop9h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:28 pm -
1 stop16h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$108
This Super.com deal was found by Cheapflights users on 9/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:25 am -
1 stop6h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/136:21 am -
1 stop5h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Sat 11/146:42 pm -
1 stop17h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 12/157:32 pm -
1 stop22h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$115
This Frontier deal was found by Cheapflights users on 9/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:21 am -
1 stop5h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 11/186:42 pm -
1 stop17h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 9/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:16 am -
1 stop5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$118
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (Priceline) |
One-way from | $90 (CheapOair) |
Popular in | March |
Cheapest in | December |
Average price | $363 |
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 7,457,451 searches. Data last updated September 22, 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 Chicago Midway - ORF Norfolk
MDWORF
Chicago Midway
Tue 11/17
6:25 pm-9:30 pm
Nonstop2h 05m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
ChicagoNorfolk
MDW Chicago Midway - ORF Norfolk
MDWORF
Chicago Midway
Sat 11/7
8:25 am-11:35 am
Nonstop2h 10m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
ChicagoNorfolk
ORD Chicago O'Hare Intl - ORF Norfolk
ORDORF
Chicago O'Hare Intl
Sat 11/7
4:40 pm-10:34 pm
1 stop4h 54m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$140
ChicagoNorfolk
MDW Chicago Midway - ORF Norfolk
MDWORF
Chicago Midway
Mon 10/26
6:44 pm-11:32 pm
1 stop3h 48m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
ChicagoNorfolk
MDW Chicago Midway - ORF Norfolk
MDWORF
Chicago Midway
Thu 10/15
6:44 pm-11:32 pm
1 stop3h 48m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
ChicagoNorfolk
ORD Chicago O'Hare Intl - ORF Norfolk
ORDORF
Chicago O'Hare Intl
Wed 11/18
7:29 am-10:53 am
Nonstop2h 24m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
ChicagoNorfolk
ORD Chicago O'Hare Intl - ORF Norfolk
ORDORF
Chicago O'Hare Intl
Mon 10/26
7:00 am-11:45 am
1 stop3h 45m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$169
ChicagoNorfolk
ORD Chicago O'Hare Intl - ORF Norfolk
ORDORF
Chicago O'Hare Intl
Wed 10/21
10:05 am-5:46 pm
1 stop6h 41m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$169
ChicagoNorfolk
MDW Chicago Midway - ORF Norfolk
MDWORF
Chicago Midway
Tue 10/20
6:21 am-6:46 pm
2 stops35h 25m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$171
ChicagoNorfolk
MDW Chicago Midway - ORF Norfolk
MDWORF
Chicago Midway
Fri 10/16
6:44 pm-11:32 pm
1 stop3h 48m
Norfolk
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
Showing 1-10 of 35 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.
MDW-ORF
ORD-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
MDW-ORF
ORD-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 September 22, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 6% 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 September 22, 2026.
The most flights from CHI to I1W are scheduled on a Monday (27 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?
Airfare is typical for this route at the moment.
Chicago to Isle of Wight flights typically cost between $298 and $453 in November.The cheapest round-trip price found within the last 5 days was $299 on Frontier (Nov 21-Nov 24).
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 September 19, 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. Tuesday 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 September 22, 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.
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Food
7.0
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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Alternative routes for Chicago to Isle of Wight
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Complete your trip
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Find flights from Chicago to Isle of Wight, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Isle of Wight flights
Browse other Chicago and Isle of Wight flight options. Last updated on September 22, 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 September 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$396 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$226 | Average$320 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$263 | Average$418 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$265 | Average$466 | FlexibilityNo cancel fee | On-time71% |