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Isle of Wight

$81+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Jul 21 — Jul 281
Mon 7/21
Mon 7/28
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 July 16, 2025.

Round-trip from

$231
(Mytrip)

One-way from

$81
(Priceline)

Popular in

October

Cheapest in

November

Average price

$513
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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High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 6% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 16, 2025.

This Mytrip deal was found by Cheapflights users on 7/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/286:15 amMDW - ORF
1 stop8h 03mFrontier
Thu 9/412:19 pmORF - MDW
1 stop12h 01mFrontier
Deal found 7/14$231
This Southwest deal was found by Cheapflights users on 7/15. 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 9/46:30 amMDW - ORF
2 stops6h 35mSouthwest
Mon 9/85:30 amORF - MDW
Nonstop2h 00mSouthwest
Deal found 7/15$232
This Delta deal was found by Cheapflights users on 7/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/66:00 amMDW - ORF
1 stop4h 33mDelta
Tue 8/126:00 amORF - MDW
1 stop3h 35mDelta
Deal found 7/16$237

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 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 8/28

6:15 am-3:18 pm

1 stop8h 03m

Norfolk

Thu 9/4

12:19 pm-11:20 pm

1 stop12h 01m

$231

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 9/4

6:30 am-2:05 pm

2 stops6h 35m

Norfolk

Mon 9/8

5:30 am-6:30 am

Nonstop2h 00m

$232

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 8/6

6:00 am-11:33 am

1 stop4h 33m

Norfolk

Tue 8/12

6:00 am-8:35 am

1 stop3h 35m

$237

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 10/8

8:00 am-2:27 pm

1 stop5h 27m

$81

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mon 8/18

11:10 am-2:15 pm

Nonstop2h 05m

$109

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 8/13

6:04 am-2:35 pm

1 stop7h 31m

$119

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 8/22

9:32 am-10:34 pm

2 stops12h 02m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/14

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 July 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 July 13, 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 July 16, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Frontier 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
4,241 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,959 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,256 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Isle of Wight one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $81. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago Midway Airport to Isle of Wight for a low price.

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

    On average you can expect to pay $220 for a flight from Chicago Midway Airport to Isle of Wight. The cheapest flight overall is $53 while the most popular route, (Chicago Midway - Norfolk) is currently priced at $217.

  • 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.

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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 July 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$230Average$379FlexibilityNo cancel feeOn-time63%

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