$65+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Apr 14 — Apr 211
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Isle of Wight with Cheapflights
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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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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 March 15, 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 March 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/116:40 am
MDW
- ORF
1 stop8h 54m
Frontier
Sat 4/1811:27 am
ORF
- MDW
1 stop8h 10m
Frontier
Deal found 3/12![Frontier logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 4/173:29 pm
MDW
- ORF
2 stops19h 46m
Multiple Airlines
Sun 4/1911:27 am
ORF
- MDW
1 stop9h 04m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 3/261:24 pm
MDW
- ORF
1 stop7h 23m
Multiple Airlines
Mon 3/308:41 pm
ORF
- MDW
2 stops25h 13m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 3/13. 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 4/187:25 am
MDW
- ORF
1 stop8h 15m
Southwest
Tue 4/216:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 3/13![Southwest logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/173:29 pm
MDW
- ORF
2 stops18h 03m
Frontier
Sun 4/1912:32 pm
ORF
- MDW
1 stop20h 32m
Frontier
Deal found 3/10![Frontier logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/96:00 am
MDW
- ORF
2 stops25h 38m
Multiple Airlines
Thu 4/1611:27 am
ORF
- MDW
1 stop11h 52m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:25 pm
MDW
- ORF
2 stops39h 13m
Frontier
Sat 4/115:29 pm
ORF
- MDW
1 stop6h 00m
Frontier
Deal found 3/14![Frontier logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 4/55:05 am
MDW
- ORF
1 stop13h 15m
Multiple Airlines
Sat 4/117:00 am
ORF
- MDW
2 stops18h 37m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$321
This Expedia deal was found by Cheapflights users on 3/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:26 am
MDW
- ORF
1 stop10h 20m
Frontier
Sun 4/269:50 am
ORF
- MDW
1 stop23h 14m
Frontier
Deal found 3/14![Frontier logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:33 pm
MDW
- ORF
1 stop21h 10m
Frontier
Mon 4/611:33 am
ORF
- MDW
1 stop11h 46m
Frontier
Deal found 3/14![Frontier logo]()
$326
This Southwest deal was found by Cheapflights users on 3/13. 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 4/255:25 pm
MDW
- ORF
1 stop4h 40m
Southwest
Sat 5/21:15 pm
ORF
- MDW
2 stops7h 50m
Southwest
Deal found 3/13![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 3/11. 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 4/187:50 am
MDW
- ORF
Nonstop2h 00m
Southwest
Mon 4/205:25 pm
ORF
- MDW
1 stop5h 55m
Southwest
Deal found 3/11![Southwest logo]()
$329
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 March 15, 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 March 15, 2026.
This Southwest deal was found by Cheapflights users on 3/11. 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 4/185:25 pm
MDW
- ORF
1 stop4h 40m
Southwest
Mon 4/202:30 pm
ORF
- MDW
2 stops6h 35m
Southwest
Deal found 3/11![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 3/11. 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.
Sat 6/135:59 pm
MDW
- ORF
1 stop4h 34m
Delta
Sat 6/205:50 am
ORF
- MDW
1 stop3h 52m
Delta
Deal found 3/11![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 3/10. 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 3/301:30 pm
MDW
- ORF
Nonstop1h 55m
Southwest
Wed 4/86:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 3/10![Southwest logo]()
$403
This Delta deal was found by Cheapflights users on 3/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:59 pm
MDW
- ORF
1 stop4h 34m
Delta
Thu 6/256:05 pm
ORF
- MDW
1 stop4h 40m
Delta
Deal found 3/14![Delta logo]()
$405
This Southwest deal was found by Cheapflights users on 3/12. 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
Sun 5/315:50 am
ORF
- MDW
2 stops7h 20m
Southwest
Deal found 3/12![Southwest logo]()
$405
This Delta deal was found by Cheapflights users on 3/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:59 am
MDW
- ORF
1 stop5h 22m
Delta
Sun 5/175:20 am
ORF
- MDW
1 stop5h 40m
Delta
Deal found 3/14![Delta logo]()
$416
This Southwest deal was found by Cheapflights users on 3/14. 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.
Thu 6/112:40 pm
MDW
- ORF
2 stops7h 45m
Southwest
Sun 6/147:20 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 3/14![Southwest logo]()
$405
Last-minute flights from Midway to Isle of WightDiscover last-minute flight deals from Midway to Isle of Wight. Data last updated March 15, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Isle of Wight. Data last updated March 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 3/261:24 pm
MDW
- ORF
1 stop7h 23m
Multiple Airlines
Mon 3/308:41 pm
ORF
- MDW
2 stops25h 13m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:33 pm
MDW
- ORF
1 stop21h 10m
Frontier
Mon 4/611:33 am
ORF
- MDW
1 stop11h 46m
Frontier
Deal found 3/14![Frontier logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:25 pm
MDW
- ORF
2 stops39h 13m
Frontier
Sat 4/115:29 pm
ORF
- MDW
1 stop6h 00m
Frontier
Deal found 3/14![Frontier logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 4/55:05 am
MDW
- ORF
1 stop13h 15m
Multiple Airlines
Sat 4/117:00 am
ORF
- MDW
2 stops18h 37m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/96:00 am
MDW
- ORF
2 stops25h 38m
Multiple Airlines
Thu 4/1611:27 am
ORF
- MDW
1 stop11h 52m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/116:40 am
MDW
- ORF
1 stop8h 54m
Frontier
Sat 4/1811:27 am
ORF
- MDW
1 stop8h 10m
Frontier
Deal found 3/12![Frontier logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 4/173:29 pm
MDW
- ORF
2 stops19h 46m
Multiple Airlines
Sun 4/1911:27 am
ORF
- MDW
1 stop9h 04m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/173:29 pm
MDW
- ORF
2 stops18h 03m
Frontier
Sun 4/1912:32 pm
ORF
- MDW
1 stop20h 32m
Frontier
Deal found 3/10![Frontier logo]()
$315
This Southwest deal was found by Cheapflights users on 3/13. 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 4/187:25 am
MDW
- ORF
1 stop8h 15m
Southwest
Tue 4/216:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 3/13![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 3/11. 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 4/187:50 am
MDW
- ORF
Nonstop2h 00m
Southwest
Mon 4/205:25 pm
ORF
- MDW
1 stop5h 55m
Southwest
Deal found 3/11![Southwest logo]()
$329
This Expedia deal was found by Cheapflights users on 3/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:26 am
MDW
- ORF
1 stop10h 20m
Frontier
Sun 4/269:50 am
ORF
- MDW
1 stop23h 14m
Frontier
Deal found 3/14![Frontier logo]()
$325
This Southwest deal was found by Cheapflights users on 3/13. 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 4/255:25 pm
MDW
- ORF
1 stop4h 40m
Southwest
Sat 5/21:15 pm
ORF
- MDW
2 stops7h 50m
Southwest
Deal found 3/13![Southwest logo]()
$328
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 March 15, 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 March 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 5/136:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 3/11![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 5/1212:27 pm
MDW
- ORF
1 stop21h 44m
Frontier
Deal found 3/13![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 4/156:30 am
MDW
- ORF
1 stop27h 02m
Frontier
Deal found 3/13![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 3/13. 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 5/106:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 3/13![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/86:00 am
MDW
- ORF
1 stop27h 24m
Frontier
Deal found 3/10![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1912:27 pm
MDW
- ORF
1 stop21h 44m
Frontier
Deal found 3/14![Frontier logo]()
$88
This Priceline deal was found by Cheapflights users on 3/10. 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 5/99:14 am
MDW
- ORF
1 stop7h 35m
Frontier
Deal found 3/10![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/62:20 pm
MDW
- ORF
1 stop19h 04m
Frontier
Deal found 3/10![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Mon 5/116:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 3/15![Frontier logo]()
$96
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 March 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $295 (Kiwi.com) |
One-way from | $65 (Kiwi.com) |
Popular in | November |
Cheapest in | September |
Average price | $392 |
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 March 15, 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
Sat 4/18
5:25 pm-11:05 pm
1 stop4h 40m
Norfolk
Mon 4/20
2:30 pm-8:05 pm
2 stops6h 35m
$344
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 6/13
5:59 pm-11:33 pm
1 stop4h 34m
Norfolk
Sat 6/20
5:50 am-8:42 am
1 stop3h 52m
$383
Quickest round-trip
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Mon 3/30
1:30 pm-4:25 pm
Nonstop1h 55m
Norfolk
Wed 4/8
6:25 pm-7:35 pm
Nonstop2h 10m
$403
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 6/11
5:59 pm-11:33 pm
1 stop4h 34m
Norfolk
Thu 6/25
6:05 pm-9:45 pm
1 stop4h 40m
$405
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 5/29
7:00 pm-10:00 pm
Nonstop2h 00m
Norfolk
Sun 5/31
5:50 am-12:10 pm
2 stops7h 20m
$405
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 6/11
2:40 pm-11:25 pm
2 stops7h 45m
Norfolk
Sun 6/14
7:20 pm-8:25 pm
Nonstop2h 05m
$405
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 5/14
10:59 am-5:21 pm
1 stop5h 22m
Norfolk
Sun 5/17
5:20 am-10:00 am
1 stop5h 40m
$416
Cheapest one-way
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Tue 5/12
6:00 am-11:11 am
1 stop28h 11m
$75
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 4/17
2:15 pm-10:32 am
1 stop19h 17m
$128
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Thu 5/7
4:09 pm-10:24 am
2 stops17h 15m
$129
Showing 1-10 of 19 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 month to book a flight from Chicago Midway Airport to Isle of Wight?
Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Isle of Wight (average of $155). Flying from Chicago Midway Airport to Isle of Wight in December is currently the most expensive (average of $569). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 March 15, 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 10% on the cost of your flight, compared to a flight at noon.
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 March 14, 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.
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 March 15, 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
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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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 March 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$360 | FlexibilityNo cancel fee | On-time63% |