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Isle of Wight

$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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 September 16, 2025.

Round-trip from

$199
(Kiwi.com)

One-way from

$71
(Kiwi.com)

Popular in

October

Cheapest in

September

Average price

$254
From Chicago Midway to Isle of Wight
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One-way flight from Chicago Midway to Isle of Wight
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Highest demand for flights based on searches. 7% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Isle of Wight

Cheapest flights from Midway to Isle of Wight
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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 10/148:05 amMDW - ORF
1 stop7h 44mFrontier
Tue 10/216:15 pmORF - MDW
1 stop20h 23mFrontier
Deal found 9/15$199
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/1611:49 amMDW - ORF
1 stop27h 50mMultiple Airlines
Thu 10/235:38 pmORF - MDW
1 stop23h 42mMultiple Airlines
Deal found 9/16$203
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/111:36 amMDW - ORF
1 stop24h 40mFrontier
Sun 11/23:49 pmORF - MDW
1 stop27h 00mFrontier
Deal found 9/16$207
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/411:21 amMDW - ORF
1 stop28h 36mFrontier
Mon 10/612:19 pmORF - MDW
1 stop12h 22mFrontier
Deal found 9/15$212
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/236:20 amMDW - ORF
1 stop7h 34mMultiple Airlines
Mon 10/275:24 amORF - MDW
2 stops11h 45mMultiple Airlines
Deal found 9/15$218
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 10/148:05 amMDW - ORF
1 stop7h 44mMultiple Airlines
Mon 10/204:57 pmORF - MDW
2 stops21h 41mMultiple Airlines
Deal found 9/15$227
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 10/21:49 pmMDW - ORF
2 stops20h 35mFrontier
Sun 10/55:47 pmORF - MDW
1 stop14h 36mFrontier
Deal found 9/14$232
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 9/197:15 amMDW - ORF
1 stop9h 35mFrontier
Sun 9/215:47 pmORF - MDW
2 stops25h 56mFrontier
Deal found 9/15$236
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/186:15 amMDW - ORF
1 stop5h 12mMultiple Airlines
Mon 10/205:38 pmORF - MDW
2 stops21h 00mMultiple Airlines
Deal found 9/15$239

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 September 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Isle of Wight that are best for you.

Fly from

Midway

Fly to

Isle of Wight

Route

Depart

Return

Price

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 10/14

8:05 am-4:49 pm

1 stop7h 44m

Norfolk

Tue 10/21

6:15 pm-1:38 pm

1 stop20h 23m

$199

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 10/14

8:05 am-4:49 pm

1 stop7h 44m

Norfolk

Mon 10/20

4:57 pm-1:38 pm

2 stops21h 41m

$227

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 10/23

6:20 am-2:54 pm

1 stop7h 34m

Norfolk

Mon 10/27

7:00 am-4:09 pm

1 stop10h 09m

$241

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 10/14

8:05 am-4:49 pm

1 stop7h 44m

Norfolk

Sun 10/19

7:05 am-11:46 pm

2 stops17h 41m

$249

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 10/14

6:05 pm-9:05 pm

Nonstop2h 00m

Norfolk

Tue 10/21

5:35 am-6:45 am

Nonstop2h 10m

$275

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 10/15

6:05 pm-9:05 pm

Nonstop2h 00m

Norfolk

Sat 11/1

3:15 pm-4:25 pm

Nonstop2h 10m

$275

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 10/15

1:25 pm-4:25 pm

Nonstop2h 00m

Norfolk

Wed 10/22

6:25 pm-7:35 pm

Nonstop2h 10m

$275

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 10/8

8:05 am-10:03 pm

2 stops12h 58m

Norfolk

Thu 10/9

4:14 pm-11:46 pm

1 stop8h 32m

$289

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 10/18

1:05 pm-4:05 pm

Nonstop2h 00m

Norfolk

Mon 10/20

5:30 am-6:40 am

Nonstop2h 10m

$294

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 12/3

6:05 pm-9:05 pm

Nonstop2h 00m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 16 results
1
2

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.
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

What is the cheapest month to book a flight from Chicago Midway Airport to Isle of Wight?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Isle of Wight (average of $281). Flying from Chicago Midway Airport to Isle of Wight in March is currently the most expensive (average of $351). 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 September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Isle of Wight as you normally would.

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 September 14, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Isle of Wight flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Isle of Wight

Get insights into the airlines that provide service to Isle of Wight. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Isle of Wight. Reviews last updated September 16, 2025.
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.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago Midway Airport to Isle of Wight?

    For as low as $199, Frontier can have you in Isle of Wight from Chicago Midway Airport in 7h 44m. Airlines will cover a distance of 702 mi.

  • What are the cheapest flights from Chicago Midway Airport to Isle of Wight?

    On average you can expect to pay $342 for a flight from Chicago Midway Airport to Isle of Wight. The cheapest flight overall is $78 while the most popular route, (Chicago Midway - Norfolk) is currently priced at $192.

  • Can I find deals for flights from Midway to Isle of Wight that include hotel bookings?

    Yes. In addition to deals on Midway to Isle of Wight flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Isle of Wight?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Isle of Wight.

  • Can I find deals for business class flights from Midway to Isle of Wight?

    Yes. Cheapflights offers flight deals from Midway to Isle of Wight by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Isle of Wight?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Isle of Wight (average of $281). Flying from Chicago Midway Airport to Isle of Wight in March is currently the most expensive (average of $351). 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.

See more FAQs

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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.
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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$213Average$369FlexibilityNo cancel feeOn-time63%

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