$116+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Aug 28 — Sep 41
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
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.Cheap flight deals from Midway to Isle of Wight
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Best
Last-minute
One-way
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 29, 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 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:25 am
MDW
- ORF
2 stops12h 20m
Multiple Airlines
Mon 11/1612:57 pm
ORF
- MDW
1 stop23h 01m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Sun 8/231:20 pm
ORF
- MDW
1 stop22h 35m
Frontier
Deal found 7/27![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:25 am
MDW
- ORF
1 stop27h 37m
Frontier
Mon 11/212:57 pm
ORF
- MDW
1 stop9h 56m
Frontier
Deal found 7/25![Frontier logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:03 pm
MDW
- ORF
1 stop22h 59m
Frontier
Sat 10/2412:57 pm
ORF
- MDW
1 stop10h 01m
Frontier
Deal found 7/25![Frontier logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:05 am
MDW
- ORF
2 stops35h 43m
Frontier
Tue 9/151:18 pm
ORF
- MDW
1 stop5h 28m
Frontier
Deal found 7/28![Frontier logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1411:06 am
MDW
- ORF
1 stop23h 15m
Frontier
Mon 8/1712:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/24![Frontier logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:50 am
MDW
- ORF
2 stops23h 25m
Multiple Airlines
Tue 9/151:18 pm
ORF
- MDW
1 stop5h 28m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:50 am
MDW
- ORF
2 stops29h 36m
Multiple Airlines
Sun 9/61:20 pm
ORF
- MDW
1 stop22h 35m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:25 am
MDW
- ORF
1 stop5h 04m
Frontier
Sat 9/1912:57 pm
ORF
- MDW
1 stop5h 54m
Frontier
Deal found 7/25![Frontier logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:50 am
MDW
- ORF
2 stops27h 21m
Frontier
Mon 9/71:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/26![Frontier logo]()
$308
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 29, 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 29, 2026.
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:15 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Sat 9/194:00 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 7/28![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:05 am
MDW
- ORF
1 stop4h 57m
Delta
Mon 9/285:02 pm
ORF
- MDW
1 stop6h 42m
Delta
Deal found 7/28![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:25 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Wed 9/168:05 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/26![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:05 am
MDW
- ORF
Nonstop2h 00m
Southwest
Sat 10/246:25 am
ORF
- MDW
1 stop5h 15m
Southwest
Deal found 7/25![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/83:05 pm
MDW
- ORF
1 stop4h 50m
Southwest
Tue 9/156:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 7/28![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
MDW
- ORF
1 stop3h 55m
Southwest
Mon 8/248:00 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/27![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:50 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Tue 9/88:05 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/28![Southwest logo]()
$338
Last-minute flights from Midway to Isle of WightDiscover last-minute flight deals from Midway to Isle of Wight. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Isle of Wight. Data last updated July 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1411:06 am
MDW
- ORF
1 stop23h 15m
Frontier
Mon 8/1712:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/24![Frontier logo]()
$294
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Mon 8/248:00 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/28![Southwest logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 am
MDW
- ORF
1 stop5h 20m
Multiple Airlines
Mon 8/2412:04 pm
ORF
- MDW
2 stops11h 43m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 am
MDW
- ORF
1 stop5h 40m
Delta
Mon 8/246:14 pm
ORF
- MDW
1 stop5h 22m
Delta
Deal found 7/28![Delta logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Sun 8/231:20 pm
ORF
- MDW
1 stop22h 35m
Frontier
Deal found 7/27![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:26 pm
MDW
- ORF
2 stops37h 59m
Frontier
Thu 9/31:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/28![Frontier logo]()
$316
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Thu 9/36:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 7/27![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Sun 8/306:30 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 7/25![Southwest logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Sun 8/305:06 pm
ORF
- MDW
2 stops30h 41m
Frontier
Deal found 7/28![Frontier 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 July 29, 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 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:05 am
MDW
- ORF
1 stop29h 20m
Frontier
Deal found 7/28![Frontier logo]()
$116
This Super.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/25![Frontier logo]()
$123
This iWofly deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/24![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:25 am
MDW
- ORF
1 stop28h 04m
Frontier
Deal found 7/27![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:25 am
MDW
- ORF
1 stop5h 04m
Frontier
Deal found 7/26![Frontier logo]()
$127
This Trip.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/28![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:25 am
MDW
- ORF
1 stop28h 37m
Frontier
Deal found 7/26![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/25![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:25 am
MDW
- ORF
1 stop27h 37m
Frontier
Deal found 7/24![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:40 am
MDW
- ORF
1 stop28h 22m
Frontier
Deal found 7/24![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:05 am
MDW
- ORF
1 stop28h 10m
Frontier
Deal found 7/26![Frontier logo]()
$139
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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $282 (Kiwi.com) |
One-way from | $116 (Kiwi.com) |
Popular in | November |
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 29, 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
Sat 9/12
3:15 pm-6:20 pm
Nonstop2h 05m
Norfolk
Sat 9/19
4:00 pm-5:05 pm
Nonstop2h 05m
$317
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 9/9
6:25 pm-9:35 pm
Nonstop2h 10m
Norfolk
Wed 9/16
8:05 am-9:05 am
Nonstop2h 00m
$317
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 10/10
8:05 am-11:05 am
Nonstop2h 00m
Norfolk
Sat 10/24
6:25 am-10:40 am
1 stop5h 15m
$327
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Tue 9/8
3:05 pm-8:55 pm
1 stop4h 50m
Norfolk
Tue 9/15
6:15 pm-7:20 pm
Nonstop2h 05m
$327
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 8/20
1:00 pm-5:55 pm
1 stop3h 55m
Norfolk
Mon 8/24
8:00 am-9:00 am
Nonstop2h 00m
$327
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 9/24
6:05 am-12:02 pm
1 stop4h 57m
Norfolk
Mon 9/28
5:02 pm-10:44 pm
1 stop6h 42m
$337
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 9/4
6:50 pm-10:00 pm
Nonstop2h 10m
Norfolk
Tue 9/8
8:05 am-9:05 am
Nonstop2h 00m
$338
Cheapest one-way
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 9/3
6:50 pm-10:00 pm
Nonstop2h 10m
$159
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Mon 8/24
9:00 am-12:10 pm
Nonstop2h 10m
$159
Quickest one-way
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Tue 10/27
6:10 pm-9:05 pm
Nonstop1h 55m
$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 29, 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?
Airfare is below average for this route at the moment.
Chicago Midway Airport to Isle of Wight flights typically cost between $287 and $339 in November.The cheapest round-trip price found within the last 5 days was $282 on Multiple Airlines (Nov 12-Nov 16).
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 25, 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. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Isle of Wight
Get insights into the airlines that provide service to Isle of Wight. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Isle of Wight. Reviews last updated July 29, 2026.
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.
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
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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Complete your trip
Complete your trip to Isle of Wight by adding a car rental and/or hotel reservation to your travel itinerary.
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Midway and Isle of Wight flights
Browse other Midway and Isle of Wight flight options. Last updated on July 29, 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 July 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Isle of Wight flights
Consider these flights traveling from Midway to Isle of Wight.
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 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$383 | FlexibilityNo cancel fee | On-time63% |