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Isle of Wight

$89+ 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
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 29, 2025.

Round-trip from

$227
(Southwest)

One-way from

$89
(Frontier)

Popular in

October

Cheapest in

September

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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Highest demand for flights based on searches. 0% potential increase in price ($3 potential increase over avg. RT price).
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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 29, 2025.

This Southwest deal was found by Cheapflights users on 7/29. 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 8/1910:30 amMDW - ORF
Nonstop2h 05mSouthwest
Sat 8/236:20 amORF - MDW
1 stop5h 50mSouthwest
Deal found 7/29$227
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/296:15 amMDW - ORF
1 stop8h 03mFrontier
Mon 9/14:12 pmORF - MDW
1 stop8h 15mFrontier
Deal found 7/27$228
This Delta deal was found by Cheapflights users on 7/29. 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 9/176:30 pmMDW - ORF
1 stop4h 55mDelta
Sat 9/206:00 amORF - MDW
1 stop3h 40mDelta
Deal found 7/29$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 29, 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 8/19

10:30 am-1:35 pm

Nonstop2h 05m

Norfolk

Sat 8/23

6:20 am-11:10 am

1 stop5h 50m

$227

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 8/29

6:15 am-3:18 pm

1 stop8h 03m

Norfolk

Mon 9/1

4:12 pm-11:27 pm

1 stop8h 15m

$228

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 9/17

6:30 pm-12:25 am

1 stop4h 55m

Norfolk

Sat 9/20

6:00 am-8:40 am

1 stop3h 40m

$237

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 10/8

8:00 am-2:27 pm

1 stop5h 27m

$89

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 9/3

10:30 am-1:35 pm

Nonstop2h 05m

$109

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mon 8/25

6:00 am-12:52 pm

1 stop5h 52m

$180

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 8/8

1:11 pm-4:25 pm

3 stops26h 14m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 29, 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 27, 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 29, 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
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $89. 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 $152 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 $205.

  • 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$230Average$379FlexibilityNo cancel feeOn-time63%

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