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Isle of Wight

$64+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap 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 December 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/306:14 amMDW - ORF
2 stops30h 52mMultiple Airlines
Sat 1/33:01 pmORF - MDW
1 stop6h 52mMultiple Airlines
Deal found 12/14$501
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/306:14 amMDW - ORF
1 stop27h 18mFrontier
Sat 1/33:01 pmORF - MDW
1 stop6h 52mFrontier
Deal found 12/14$502
This Trip.com deal was found by Cheapflights users on 12/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:12 amMDW - ORF
1 stop6h 27mFrontier
Mon 12/292:04 pmORF - MDW
1 stop9h 08mFrontier
Deal found 12/16$509
This Trip.com deal was found by Cheapflights users on 12/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:12 amMDW - ORF
1 stop6h 27mFrontier
Tue 12/303:11 pmORF - MDW
1 stop7h 47mFrontier
Deal found 12/15$510
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:05 pmMDW - ORF
Nonstop2h 00mSouthwest
Mon 12/295:40 amORF - MDW
Nonstop2h 10mSouthwest
Deal found 12/16$513
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:05 pmMDW - ORF
Nonstop2h 00mSouthwest
Sun 12/288:05 pmORF - MDW
Nonstop2h 10mSouthwest
Deal found 12/16$524
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/246:12 amMDW - ORF
2 stops30h 54mMultiple Airlines
Mon 12/292:04 pmORF - MDW
1 stop9h 08mMultiple Airlines
Deal found 12/16$566
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/256:12 amMDW - ORF
2 stops11h 33mMultiple Airlines
Sat 12/275:47 pmORF - MDW
1 stop5h 25mMultiple Airlines
Deal found 12/15$592
This Southwest deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:50 amMDW - ORF
1 stop6h 55mSouthwest
Sat 12/279:45 amORF - MDW
1 stop8h 30mSouthwest
Deal found 12/15$616

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 December 16, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$175
(Kiwi.com)

One-way from

$64
(Priceline)

Popular in

November

Cheapest in

September

Average price

$569
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Norfolk flights.
Search Deals
From Chicago Midway to Isle of Wight
Search Deals
One-way flight from Chicago Midway to Isle of Wight
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($73 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 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

Thu 1/8

6:10 am-9:50 pm

2 stops14h 40m

Norfolk

Mon 1/12

6:45 am-11:09 pm

1 stop17h 24m

$194

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 2/19

12:25 pm-10:37 am

1 stop21h 12m

Norfolk

Sat 2/21

6:45 am-2:55 pm

1 stop9h 10m

$195

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 1/22

5:01 pm-10:48 am

1 stop16h 47m

Norfolk

Sun 1/25

11:43 am-10:19 pm

1 stop11h 36m

$214

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 3/12

11:00 am-5:48 pm

1 stop5h 48m

Norfolk

Sat 3/14

3:26 pm-11:32 pm

1 stop9h 06m

$231

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 1/13

11:21 am-5:28 pm

1 stop5h 07m

Norfolk

Tue 1/20

1:25 pm-5:29 pm

1 stop5h 04m

$269

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 1/15

9:13 am-9:50 pm

2 stops11h 37m

Norfolk

Fri 1/23

11:43 am-10:19 pm

1 stop11h 36m

$279

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 1/24

4:30 pm-12:16 am

1 stop6h 46m

Norfolk

Tue 2/3

5:35 am-8:52 am

1 stop4h 17m

$283

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 2/19

6:10 pm-9:10 pm

Nonstop2h 00m

Norfolk

Sat 2/21

5:50 am-7:05 am

Nonstop2h 15m

$293

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 3/7

6:15 am-2:31 pm

1 stop7h 16m

Norfolk

Sat 3/14

3:26 pm-11:32 pm

1 stop9h 06m

$300

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sun 1/18

5:59 pm-12:16 am

1 stop5h 17m

Norfolk

Fri 1/23

3:36 pm-10:22 pm

1 stop7h 46m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 22 results
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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, 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 December 16, 2025.

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 16% on the cost of your flight, compared to a flight in the afternoon.

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 December 13, 2025.

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 December 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
7.9
Good
4,250 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

7.9

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

7.9

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 $269, Frontier can have you in Isle of Wight from Chicago Midway Airport in 5h 07m. Airlines will cover a distance of 702 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    On average you can expect to pay $344 for a flight from Chicago Midway Airport to Isle of Wight. The cheapest flight overall is $165 while the most popular route, (Chicago Midway - Norfolk) is currently priced at $195.

  • 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, 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.

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

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