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Isle of Wight

$67+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
févr. 28 — mars 71
sam. 2/28
sam. 3/7
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 janvier 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
mer. 2/187:00 am
MDW
-
ORF
1 stop26h 51m
Multiple Airlines
sam. 2/216:45 am
ORF
-
MDW
1 stop9h 10m
Multiple Airlines
Deal found 1/28$152
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
mer. 2/116:15 am
MDW
-
ORF
1 stop27h 36m
Frontier
ven. 2/133:18 pm
ORF
-
MDW
1 stop24h 37m
Frontier
Deal found 1/27$163
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
jeu. 2/1912:22 pm
MDW
-
ORF
1 stop21h 15m
Multiple Airlines
sam. 2/216:45 am
ORF
-
MDW
1 stop9h 10m
Multiple Airlines
Deal found 1/27$167
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
sam. 2/289:15 am
MDW
-
ORF
2 stops11h 35m
Multiple Airlines
lun. 3/211:39 am
ORF
-
MDW
1 stop11h 50m
Multiple Airlines
Deal found 1/28$170
This Priceline deal was found by Cheapflights users on 1/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 2/288:00 am
MDW
-
ORF
1 stop6h 52m
Frontier
lun. 3/211:39 am
ORF
-
MDW
1 stop9h 08m
Frontier
Deal found 1/28$185
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
ven. 2/203:00 pm
MDW
-
ORF
2 stops29h 50m
Multiple Airlines
lun. 2/2311:39 am
ORF
-
MDW
1 stop9h 08m
Multiple Airlines
Deal found 1/28$186
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
ven. 2/277:53 pm
MDW
-
ORF
2 stops18h 59m
Frontier
lun. 3/211:39 am
ORF
-
MDW
1 stop11h 50m
Frontier
Deal found 1/28$191
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
jeu. 2/1912:22 pm
MDW
-
ORF
1 stop21h 15m
Multiple Airlines
dim. 2/2211:32 am
ORF
-
MDW
2 stops26h 36m
Multiple Airlines
Deal found 1/28$192
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
ven. 2/277:30 am
MDW
-
ORF
1 stop13h 20m
Multiple Airlines
lun. 3/211:39 am
ORF
-
MDW
1 stop9h 08m
Multiple Airlines
Deal found 1/28$194
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
lun. 2/239:22 pm
MDW
-
ORF
1 stop13h 43m
Frontier
ven. 2/2711:32 am
ORF
-
MDW
1 stop8h 06m
Frontier
Deal found 1/27$195
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
mer. 2/116:15 am
MDW
-
ORF
2 stops35h 11m
Multiple Airlines
ven. 2/1311:32 am
ORF
-
MDW
1 stop7h 21m
Multiple Airlines
Deal found 1/27$198

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 janvier 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$152
(Kiwi.com)

One-way from

$67
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$397
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 ($70 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 January 2026
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 janvier 29, 2026.
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

ven. 5/8

9:14 am-5:49 pm

1 stop7h 35m

Norfolk

lun. 5/11

11:19 am-7:31 pm

1 stop9h 12m

$216

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

sam. 5/9

9:14 am-5:49 pm

1 stop7h 35m

Norfolk

sam. 5/16

6:43 pm-8:04 am

1 stop14h 21m

$231

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

sam. 3/7

6:15 am-2:31 pm

1 stop7h 16m

Norfolk

sam. 3/14

3:26 pm-9:45 pm

1 stop7h 19m

$248

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

jeu. 4/30

9:14 am-5:49 pm

1 stop7h 35m

Norfolk

dim. 5/3

11:19 am-7:31 pm

1 stop9h 12m

$270

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

mar. 3/10

6:05 pm-9:05 pm

Nonstop2h 00m

Norfolk

mer. 3/18

6:30 pm-7:50 pm

Nonstop2h 20m

$282

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

ven. 3/13

1:30 pm-4:25 pm

Nonstop1h 55m

Norfolk

mar. 3/17

6:30 pm-7:50 pm

Nonstop2h 20m

$282

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

mar. 3/10

9:35 am-4:19 pm

1 stop5h 44m

Norfolk

mer. 3/18

1:39 pm-5:22 pm

1 stop4h 43m

$287

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

ven. 3/27

6:34 pm-12:24 am

1 stop4h 50m

Norfolk

mer. 4/1

5:45 am-8:53 am

1 stop4h 08m

$302

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

sam. 2/28

6:05 pm-9:05 pm

Nonstop2h 00m

Norfolk

lun. 3/2

11:50 am-5:35 pm

1 stop6h 45m

$302

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

ven. 3/13

6:07 pm-12:23 am

1 stop5h 16m

Norfolk

mar. 3/17

5:45 am-8:53 am

1 stop4h 08m

$302

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 18 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 janvier 29, 2026.

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 26% 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 January 24, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Isle of Wight flight should consider departing on Wednesday at noon 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 janvier 29, 2026.
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
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

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
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

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 $282, Frontier can have you in Isle of Wight from Chicago Midway Airport in 2h. 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.

  • 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.

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 janvier 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$213Average$372FlexibilityNo cancel feeOn-time63%

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