$71+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
May 31 — Jun 71
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 May 1, 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 May 1, 2026.
This Southwest deal was found by Cheapflights users on 4/26. 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.
Sat 7/256:25 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Sat 8/16:55 pm
ORF
- MDW
1 stop5h 25m
Southwest
Deal found 4/26![Southwest logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Thu 6/252:46 pm
MDW
- ORF
2 stops17h 27m
Multiple Airlines
Sun 6/2812:21 pm
ORF
- MDW
1 stop23h 48m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 7/2512:11 pm
MDW
- ORF
1 stop22h 10m
Multiple Airlines
Sat 8/110:31 pm
ORF
- MDW
2 stops46h 59m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$309
This Expedia deal was found by Cheapflights users on 4/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:21 am
MDW
- ORF
1 stop10h 25m
Frontier
Tue 5/512:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 4/26![Frontier logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/143:07 pm
MDW
- ORF
2 stops26h 42m
Multiple Airlines
Wed 5/2012:06 pm
ORF
- MDW
1 stop10h 56m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/2512:27 pm
MDW
- ORF
1 stop21h 59m
Frontier
Mon 6/2912:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Deal found 4/30![Frontier logo]()
$314
This Southwest deal was found by Cheapflights users on 5/1. 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 5/276:05 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Wed 6/36:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 5/1![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 6/206:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Sun 6/289:35 pm
ORF
- MDW
2 stops38h 37m
Frontier
Deal found 4/26![Frontier logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 7/2412:11 pm
MDW
- ORF
1 stop22h 03m
Frontier
Mon 7/2712:21 pm
ORF
- MDW
1 stop10h 47m
Frontier
Deal found 4/30![Frontier logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 5/216:00 am
MDW
- ORF
2 stops13h 17m
Frontier
Mon 5/2512:06 pm
ORF
- MDW
1 stop11h 16m
Frontier
Deal found 4/27![Frontier logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 5/224:28 pm
MDW
- ORF
2 stops25h 21m
Multiple Airlines
Tue 5/2612:06 pm
ORF
- MDW
1 stop10h 56m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 6/2711:59 am
MDW
- ORF
2 stops20h 14m
Multiple Airlines
Sun 7/512:21 pm
ORF
- MDW
1 stop23h 46m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$326
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 May 1, 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 May 1, 2026.
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Mon 7/63:30 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 4/28![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:22 am
MDW
- ORF
1 stop5h 40m
Delta
Mon 5/258:00 am
ORF
- MDW
1 stop4h 56m
Delta
Deal found 4/27![Delta logo]()
$375
This Southwest deal was found by Cheapflights users on 4/26. 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.
Fri 5/297:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Tue 6/26:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 4/26![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sat 7/47:10 am
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 4/28![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 4/29. 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 7/912:45 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Sun 7/197:20 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 4/29![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 4/30. 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.
Mon 6/82:40 pm
MDW
- ORF
2 stops7h 45m
Southwest
Wed 6/1012:25 pm
ORF
- MDW
2 stops8h 30m
Southwest
Deal found 4/30![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 4/30. 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 5/287:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Sun 5/318:35 pm
ORF
- MDW
1 stop4h 45m
Southwest
Deal found 4/30![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 4/27. 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.
Sun 7/197:45 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sun 7/267:45 pm
ORF
- MDW
1 stop5h 35m
Southwest
Deal found 4/27![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 4/30. 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 6/257:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Mon 6/2912:15 pm
ORF
- MDW
1 stop5h 55m
Southwest
Deal found 4/30![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 5/1. 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 7/186:30 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Sat 7/257:30 am
ORF
- MDW
1 stop8h 40m
Southwest
Deal found 5/1![Southwest logo]()
$373
Last-minute flights from Midway to Isle of WightDiscover last-minute flight deals from Midway to Isle of Wight. Data last updated May 1, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Isle of Wight. Data last updated May 1, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:21 am
MDW
- ORF
1 stop10h 25m
Frontier
Tue 5/512:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 4/26![Frontier logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/143:07 pm
MDW
- ORF
2 stops26h 42m
Multiple Airlines
Wed 5/2012:06 pm
ORF
- MDW
1 stop10h 56m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 5/1412:19 pm
MDW
- ORF
1 stop21h 52m
Frontier
Sun 5/178:49 pm
ORF
- MDW
1 stop20h 08m
Frontier
Deal found 4/27![Frontier logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 5/216:00 am
MDW
- ORF
2 stops13h 17m
Frontier
Mon 5/2512:06 pm
ORF
- MDW
1 stop11h 16m
Frontier
Deal found 4/27![Frontier logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 5/224:28 pm
MDW
- ORF
2 stops25h 21m
Multiple Airlines
Tue 5/2612:06 pm
ORF
- MDW
1 stop10h 56m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 5/2212:04 pm
MDW
- ORF
1 stop22h 11m
Frontier
Wed 6/312:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 4/29![Frontier logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/2212:04 pm
MDW
- ORF
1 stop22h 11m
Frontier
Mon 5/2512:06 pm
ORF
- MDW
1 stop24h 06m
Frontier
Deal found 4/30![Frontier logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/2311:59 am
MDW
- ORF
1 stop22h 12m
Frontier
Mon 5/2512:06 pm
ORF
- MDW
1 stop11h 16m
Frontier
Deal found 4/28![Frontier logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/2311:59 am
MDW
- ORF
1 stop22h 12m
Frontier
Tue 5/2612:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 4/30![Frontier logo]()
$328
This Southwest deal was found by Cheapflights users on 4/26. 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.
Sat 5/237:50 am
MDW
- ORF
Nonstop2h 00m
Southwest
Tue 5/266:25 am
ORF
- MDW
1 stop6h 45m
Southwest
Deal found 4/26![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 5/1. 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 5/276:05 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Wed 6/36:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 5/1![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 4/26. 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.
Fri 5/297:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Tue 6/26:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 4/26![Southwest logo]()
$340
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 May 1, 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 May 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/276:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 4/27![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/266:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 4/29![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Thu 5/286:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 4/29![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sun 6/286:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 4/29![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/16:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 4/29![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/256:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 4/30![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 7/2512:11 pm
MDW
- ORF
1 stop22h 10m
Frontier
Deal found 4/28![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/2312:27 pm
MDW
- ORF
1 stop21h 59m
Frontier
Deal found 4/29![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 4/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:52 pm
MDW
- ORF
1 stop24h 37m
Frontier
Deal found 4/27![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Sun 5/2412:27 pm
MDW
- ORF
1 stop21h 44m
Frontier
Deal found 4/27![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/296:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 4/29![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 7/1812:11 pm
MDW
- ORF
1 stop22h 10m
Frontier
Deal found 4/28![Frontier logo]()
$108
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 May 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (Southwest) |
One-way from | $71 (Kiwi.com) |
Popular in | November |
Cheapest in | September |
Average price | $381 |
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 May 1, 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
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 7/1
7:55 am-11:05 am
Nonstop2h 10m
Norfolk
Mon 7/6
3:30 pm-4:35 pm
Nonstop2h 05m
$340
Quickest round-trip
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 5/29
7:00 pm-10:00 pm
Nonstop2h 00m
Norfolk
Tue 6/2
6:25 pm-7:35 pm
Nonstop2h 10m
$340
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 7/1
7:55 am-11:05 am
Nonstop2h 10m
Norfolk
Sat 7/4
7:10 am-8:15 am
Nonstop2h 05m
$340
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 7/9
12:45 pm-3:50 pm
Nonstop2h 05m
Norfolk
Sun 7/19
7:20 pm-8:25 pm
Nonstop2h 05m
$363
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Mon 6/8
2:40 pm-11:25 pm
2 stops7h 45m
Norfolk
Wed 6/10
12:25 pm-7:55 pm
2 stops8h 30m
$366
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 5/28
7:00 pm-10:00 pm
Nonstop2h 00m
Norfolk
Sun 5/31
8:35 pm-12:20 am
1 stop4h 45m
$369
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sun 7/19
7:45 am-10:55 am
Nonstop2h 10m
Norfolk
Sun 7/26
7:45 pm-12:20 am
1 stop5h 35m
$373
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 6/25
7:40 am-10:45 am
Nonstop2h 05m
Norfolk
Mon 6/29
12:15 pm-5:10 pm
1 stop5h 55m
$373
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 7/18
6:30 pm-9:30 pm
Nonstop2h 00m
Norfolk
Sat 7/25
7:30 am-3:10 pm
1 stop8h 40m
$373
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 5/21
9:22 am-4:02 pm
1 stop5h 40m
Norfolk
Mon 5/25
8:00 am-11:56 am
1 stop4h 56m
$375
Showing 1-10 of 21 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 May 1, 2026.
It’s optimal to fly from Chicago Midway Airport to Isle of Wight in the morning. By choosing this option you can save up to 6% on the cost of your flight, compared to a flight in the evening.
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 April 25, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Isle of Wight flight should consider departing on Sunday mornings 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.
How much does it cost to fly round-trip from Chicago Midway Airport to Isle of Wight?
Reviews of airlines servicing Isle of Wight
Get insights into the airlines that provide service to Isle of Wight. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Isle of Wight. Reviews last updated May 1, 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.
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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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Alternative routes for Midway to Isle of Wight
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Isle of Wight by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Isle of Wight by cabin class
Find flights from Midway to Isle of Wight, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Isle of Wight flights
Browse other Midway and Isle of Wight flight options. Last updated on May 1, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on May 1, 2026.
Popular flight searches
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Midway to Isle of Wight flights
Consider these flights traveling from Midway to Isle of Wight.
Top 2 airlines flying from Midway to Isle of Wight
Discover the top 2 airlines 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 May 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$265 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$174 | Average$354 | FlexibilityNo cancel fee | On-time63% |