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Isle of Wight

$61+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$110
(Frontier)

One-way from

$61
(Priceline)

Popular in

October

Cheapest in

September

Average price

$666
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Norfolk flights.
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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. 2% potential increase in price ($11 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 October 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 October 30, 2025.

This Frontier deal was found by Cheapflights users on 10/30. 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.
Thu 11/136:30 amMDW - ORF
1 stop6h 55mFrontier
Mon 11/1711:29 amORF - MDW
1 stop11h 42mFrontier
Deal found 10/30$110
This Frontier deal was found by Cheapflights users on 10/30. 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.
Mon 12/86:15 amMDW - ORF
1 stop9h 05mFrontier
Fri 12/1212:00 pmORF - MDW
1 stop8h 42mFrontier
Deal found 10/30$166
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/122:06 pmMDW - ORF
2 stops22h 09mMultiple Airlines
Sun 11/169:03 pmORF - MDW
1 stop12h 29mMultiple Airlines
Deal found 10/27$187
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/133:40 pmMDW - ORF
2 stops19h 44mMultiple Airlines
Mon 11/1711:29 amORF - MDW
1 stop25h 09mMultiple Airlines
Deal found 10/29$206
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/256:05 amMDW - ORF
1 stop7h 50mMultiple Airlines
Mon 12/19:26 pmORF - MDW
2 stops36h 20mMultiple Airlines
Deal found 10/28$256
This Southwest deal was found by Cheapflights users on 10/28. 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 12/131:25 pmMDW - ORF
Nonstop1h 55mSouthwest
Sat 1/1011:15 amORF - MDW
1 stop6h 40mSouthwest
Deal found 10/28$285
This Southwest deal was found by Cheapflights users on 10/28. 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 12/46:05 pmMDW - ORF
Nonstop2h 00mSouthwest
Sat 12/65:30 pmORF - MDW
Nonstop2h 10mSouthwest
Deal found 10/28$294
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 11/246:48 pmMDW - ORF
1 stop3h 34mDelta
Tue 12/26:02 pmORF - MDW
1 stop6h 45mDelta
Deal found 10/29$296
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/256:05 amMDW - ORF
1 stop7h 50mFrontier
Mon 12/14:06 pmORF - MDW
1 stop18h 11mFrontier
Deal found 10/28$302

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 October 30, 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

Wed 11/12

2:06 pm-1:15 pm

2 stops22h 09m

Norfolk

Sun 11/16

9:03 pm-8:32 am

1 stop12h 29m

$187

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sun 1/18

2:12 pm-10:54 am

1 stop19h 42m

Norfolk

Sun 1/25

1:10 pm-11:25 pm

2 stops35h 15m

$237

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 11/25

6:05 am-2:55 pm

1 stop7h 50m

Norfolk

Mon 12/1

9:26 pm-8:46 am

2 stops36h 20m

$256

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 12/13

1:25 pm-4:20 pm

Nonstop1h 55m

Norfolk

Sat 1/10

11:15 am-4:55 pm

1 stop6h 40m

$285

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 12/4

6:05 pm-9:05 pm

Nonstop2h 00m

Norfolk

Sat 12/6

7:00 am-2:35 pm

2 stops8h 35m

$309

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 12/6

1:14 pm-5:40 pm

1 stop3h 26m

Norfolk

Mon 12/8

5:40 am-8:54 am

1 stop4h 14m

$314

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 11/20

6:05 am-8:31 pm

2 stops13h 26m

Norfolk

Fri 11/28

4:06 pm-10:43 pm

1 stop7h 37m

$341

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 12/23

6:14 am-10:32 am

1 stop27h 18m

Norfolk

Sat 12/27

5:47 pm-10:12 pm

1 stop5h 25m

$343

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mon 1/26

6:00 am-10:42 pm

2 stops15h 42m

$106

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 12/25

6:12 am-10:58 pm

2 stops15h 46m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 20 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Isle of Wight (average of $154). Flying from Chicago Midway Airport to Isle of Wight in April is currently the most expensive (average of $360). 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 October 30, 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 12% 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 October 26, 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 October 30, 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
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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 $285, Frontier can have you in Isle of Wight from Chicago Midway Airport in 1h 55m. 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 $194 for a flight from Chicago Midway Airport to Isle of Wight. The cheapest flight overall is $115 while the most popular route, (Chicago Midway - Norfolk) is currently priced at $238.

  • 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Isle of Wight (average of $154). Flying from Chicago Midway Airport to Isle of Wight in April is currently the most expensive (average of $360). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$230Average$363FlexibilityNo cancel feeOn-time63%

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