$122+ Cheap flights from Midway (MDW) 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Aug 19 — Aug 261
Round-trip
1 adult, Economy
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Find cheap flights from Midway 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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Isle of Wight
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Cheapest flights from Midway to Isle of WightExplore the most affordable flight options available from Midway to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 20, 2026.
Explore the most affordable flight options available from Midway to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Fri 8/711:06 am
MDW
- ORF
1 stop23h 15m
Frontier
Sun 8/912:10 pm
ORF
- MDW
1 stop22h 41m
Frontier
Deal found 7/17![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Fri 8/711:06 am
MDW
- ORF
1 stop23h 15m
Frontier
Tue 8/1112:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/17![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/46:05 am
MDW
- ORF
1 stop28h 10m
Frontier
Sat 8/812:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Deal found 7/17![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/412:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Wed 8/1212:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/17![Frontier logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Sun 10/116:40 am
MDW
- ORF
1 stop28h 22m
Frontier
Sun 10/1812:57 pm
ORF
- MDW
1 stop10h 01m
Frontier
Deal found 7/17![Frontier logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/2511:50 am
MDW
- ORF
2 stops29h 36m
Multiple Airlines
Sun 8/301:20 pm
ORF
- MDW
1 stop10h 27m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Fri 9/1112:03 pm
MDW
- ORF
2 stops11h 15m
Multiple Airlines
Sun 9/1312:57 pm
ORF
- MDW
1 stop10h 01m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 9/167:25 am
MDW
- ORF
2 stops14h 04m
Multiple Airlines
Sun 9/2012:57 pm
ORF
- MDW
1 stop10h 01m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 9/111:50 am
MDW
- ORF
2 stops29h 36m
Multiple Airlines
Sun 9/61:20 pm
ORF
- MDW
1 stop10h 27m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Tue 8/412:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Thu 8/612:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/18![Frontier logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Thu 8/209:26 pm
MDW
- ORF
2 stops37h 59m
Frontier
Mon 8/241:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/17![Frontier logo]()
$313
Best flights from Midway to Isle of WightDiscover carefully curated flight deals from Midway 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 20, 2026.
Discover carefully curated flight deals from Midway 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 20, 2026.
This KAYAK deal was found by Cheapflights users on 7/15. 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.
Tue 8/186:25 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Thu 8/206:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 7/15![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 7/15. 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 8/297:45 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sat 9/54:00 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 7/15![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 7/18. 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.
Sat 8/227:45 am
MDW
- ORF
Nonstop2h 10m
Southwest
Mon 8/318:00 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/18![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 7/17. 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 8/206:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Mon 8/246:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 7/17![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 7/16. 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.
Sun 8/238:50 am
MDW
- ORF
Nonstop2h 15m
Southwest
Thu 8/271:05 pm
ORF
- MDW
1 stop6h 10m
Southwest
Deal found 7/16![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 7/19. 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 8/276:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Thu 9/310:10 am
ORF
- MDW
1 stop7h 05m
Southwest
Deal found 7/19![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 7/18. 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 9/109:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sun 9/136:30 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 7/18![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 7/19. 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.
Tue 8/189:00 am
MDW
- ORF
2 stops5h 55m
Southwest
Sat 8/222:50 pm
ORF
- MDW
1 stop5h 30m
Southwest
Deal found 7/19![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 7/17. 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 8/135:30 am
MDW
- ORF
2 stops6h 00m
Southwest
Tue 8/186:15 am
ORF
- MDW
2 stops6h 50m
Southwest
Deal found 7/17![Southwest logo]()
$367
Last-minute flights from Midway to Isle of WightDiscover last-minute flight deals from Midway to Isle of Wight. Data last updated July 20, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Isle of Wight. Data last updated July 20, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/46:05 am
MDW
- ORF
1 stop28h 10m
Frontier
Sat 8/812:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Deal found 7/17![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/412:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Wed 8/1212:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/17![Frontier logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Tue 8/412:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Thu 8/612:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/18![Frontier logo]()
$310
This Southwest deal was found by Cheapflights users on 7/15. 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 8/66:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Mon 8/106:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 7/15![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Fri 8/711:06 am
MDW
- ORF
1 stop23h 15m
Frontier
Sun 8/912:10 pm
ORF
- MDW
1 stop22h 41m
Frontier
Deal found 7/17![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Fri 8/711:06 am
MDW
- ORF
1 stop23h 15m
Frontier
Tue 8/1112:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/17![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Sun 8/96:05 am
MDW
- ORF
1 stop28h 10m
Multiple Airlines
Thu 8/1312:59 pm
ORF
- MDW
2 stops21h 52m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Mon 8/106:05 am
MDW
- ORF
2 stops34h 27m
Multiple Airlines
Sat 8/1512:16 pm
ORF
- MDW
1 stop10h 47m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/1111:06 am
MDW
- ORF
2 stops32h 33m
Frontier
Sat 8/1512:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Deal found 7/17![Frontier logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Thu 8/209:26 pm
MDW
- ORF
2 stops37h 59m
Frontier
Mon 8/241:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/17![Frontier logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/2511:50 am
MDW
- ORF
2 stops29h 36m
Multiple Airlines
Sun 8/301:20 pm
ORF
- MDW
1 stop10h 27m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$299
One-way flights from Midway to Isle of WightSearch for one-way flight options from Midway to Isle of Wight. Find affordable one-way fares based on user searches. Data last updated July 20, 2026.
Search for one-way flight options from Midway to Isle of Wight. Find affordable one-way fares based on user searches. Data last updated July 20, 2026.
This Priceline deal was found by Cheapflights users on 7/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/19![Frontier logo]()
$122
This Trip.com deal was found by Cheapflights users on 7/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/18![Frontier logo]()
$126
This Trip.com deal was found by Cheapflights users on 7/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/17![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 8/76:05 am
MDW
- ORF
1 stop28h 16m
Frontier
Deal found 7/16![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 7/15. 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 8/146:05 am
MDW
- ORF
1 stop28h 16m
Frontier
Deal found 7/15![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 9/177:25 am
MDW
- ORF
1 stop27h 37m
Frontier
Deal found 7/16![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Tue 8/46:05 am
MDW
- ORF
1 stop28h 10m
Frontier
Deal found 7/19![Frontier logo]()
$156
This Southwest deal was found by Cheapflights users on 7/14. 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 8/157:45 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/14![Southwest logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Sat 10/1712:03 pm
MDW
- ORF
1 stop22h 59m
Frontier
Deal found 7/18![Frontier logo]()
$166
This Southwest deal was found by Cheapflights users on 7/19. 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 9/176:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/19![Southwest logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 9/147:25 am
MDW
- ORF
2 stops15h 53m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$170
Find flight deals from Midway to Isle of Wight
Keep the following information in mind while searching for Midway to Isle of Wight flight deals. Data was last updated July 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $280 (Kiwi.com) |
One-way from | $122 (Priceline) |
Popular in | December |
Cheapest in | October |
Average price | $372 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway 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 20, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport 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
Tue 8/18
6:25 pm-9:30 pm
Nonstop2h 05m
Norfolk
Thu 8/20
6:45 pm-7:50 pm
Nonstop2h 05m
$317
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 8/29
7:45 am-10:55 am
Nonstop2h 10m
Norfolk
Sat 9/5
4:00 pm-5:05 pm
Nonstop2h 05m
$317
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 8/22
7:45 am-10:55 am
Nonstop2h 10m
Norfolk
Mon 8/31
8:00 am-9:00 am
Nonstop2h 00m
$337
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 8/20
6:50 pm-9:55 pm
Nonstop2h 05m
Norfolk
Mon 8/24
6:45 pm-7:50 pm
Nonstop2h 05m
$337
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sun 8/23
8:50 am-12:05 pm
Nonstop2h 15m
Norfolk
Thu 8/27
1:05 pm-6:15 pm
1 stop6h 10m
$350
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 8/27
6:50 pm-9:55 pm
Nonstop2h 05m
Norfolk
Thu 9/3
10:10 am-4:15 pm
1 stop7h 05m
$353
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 9/10
9:00 am-12:10 pm
Nonstop2h 10m
Norfolk
Sun 9/13
6:30 pm-7:35 pm
Nonstop2h 05m
$359
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Tue 8/18
9:00 am-3:55 pm
2 stops5h 55m
Norfolk
Sat 8/22
2:50 pm-7:20 pm
1 stop5h 30m
$362
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 8/13
5:30 am-12:30 pm
2 stops6h 00m
Norfolk
Tue 8/18
6:15 am-12:05 pm
2 stops6h 50m
$367
Cheapest one-way
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 8/15
7:45 am-10:55 am
Nonstop2h 10m
$159
Showing 1-10 of 17 resultsSorted by cheapest first
Best time to book a flight from Midway to Isle of Wight
Have a flexible travel schedule? Discover the best time to fly to Isle of Wight from Midway with our price prediction graph.
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 Midway Airport to Isle of Wight
MDW-I1W
MDW-ORF
What is the cheapest time of day to fly from MDW to I1W?
Find hourly flight availability from Midway 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 20, 2026.
It’s optimal to fly from Chicago Midway Airport to Isle of Wight in the afternoon. By choosing this option you can save up to 14% on the cost of your flight, compared to a flight in the evening.
How much does it cost to fly round-trip from Chicago Midway Airport to Isle of Wight?
What is the cheapest day to fly from Chicago Midway Airport to Isle of Wight?
Use this chart to determine the cheapest time to fly round-trip from Midway to Isle of Wight. Price data was last updated on July 18, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Isle of Wight flight should consider departing on Wednesday at noon when fares are most often at their lowest. Monday afternoons 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 20, 2026.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to Isle of Wight to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
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 Midway 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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Midway and Isle of Wight flights
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Top airline flying from Midway to Isle of Wight
Discover the top airline that operate flights from Midway 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 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$377 | FlexibilityNo cancel fee | On-time63% |