HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Isle of Wight

$79+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Isle of Wight with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 12, 2025.

Round-trip from

$244
(Southwest)

One-way from

$79
(Southwest)

Popular in

October

Cheapest in

November

Average price

$378
From Chicago Midway to Isle of Wight
Search Deals
One-way flight from Chicago Midway to Isle of Wight
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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 10/111:05 pmMDW - ORF
Nonstop2h 00mSouthwest
Mon 10/136:10 amORF - MDW
2 stops8h 10mSouthwest
Deal found 6/11$244
This Delta deal was found by Cheapflights users on 6/10. 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.
Thu 8/216:04 amMDW - ORF
1 stop5h 48mDelta
Mon 8/255:30 amORF - MDW
1 stop4h 46mDelta
Deal found 6/10$268
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Fri 7/1810:31 amMDW - ORF
2 stops28h 54mMultiple Airlines
Sun 7/203:54 pmORF - MDW
2 stops18h 47mMultiple Airlines
Deal found 6/11$305
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/56:15 amMDW - ORF
1 stop7h 12mFrontier
Sun 9/79:52 amORF - MDW
1 stop22h 47mFrontier
Deal found 6/11$310

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 June 12, 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

Sat 10/11

1:05 pm-4:05 pm

Nonstop2h 00m

Norfolk

Mon 10/13

6:10 am-1:20 pm

2 stops8h 10m

$244

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 8/21

6:04 am-12:52 pm

1 stop5h 48m

Norfolk

Mon 8/25

5:30 am-9:16 am

1 stop4h 46m

$268

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 7/18

10:31 am-4:25 pm

2 stops28h 54m

Norfolk

Sun 7/20

3:54 pm-9:41 am

2 stops18h 47m

$305

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 9/5

6:15 am-2:27 pm

1 stop7h 12m

Norfolk

Sun 9/7

9:52 am-7:39 am

1 stop22h 47m

$310

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 8/6

6:20 pm-9:25 pm

Nonstop2h 05m

$79

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 11/27

1:05 pm-6:51 pm

1 stop4h 46m

$99

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 7/31

11:37 am-9:02 pm

2 stops32h 25m

$155

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 9/5

6:15 am-2:27 pm

1 stop7h 12m

$156

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 7/18

10:31 am-4:25 pm

2 stops28h 54m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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 June 8, 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 afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Isle of Wight by month

Plan your trip to Isle of Wight by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Isle of Wight ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Isle of Wight when rainfall is around 2.9 in.

Temperature in Isle of Wight by month

Plan your trip to Isle of Wight by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Isle of Wight, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 June 12, 2025.
To help decide which airline to fly from Chicago to Isle of Wight, see what other customers have to say about Southwest, Delta and Allegiant Air. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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 Southwest, with whom users have recently found tickets for as low as $79. However, be on the lookout for offers from Delta and Allegiant Air, 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 $286 for a flight from Chicago Midway Airport to Isle of Wight. The cheapest flight overall is $139 while the most popular route, (Chicago Midway - Norfolk) is currently priced at $157.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Isle of Wight

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Reagan-National flights
Midway to Dulles Intl flights
O'Hare Intl to Raleigh flights
O'Hare Intl to Norfolk flights
Midway to Reagan-National flights
O'Hare Intl to Richmond flights
O'Hare Intl to Charlottesville flights
O'Hare Intl to Greensboro flights
Midway to Norfolk flights
Midway to Raleigh flights
O'Hare Intl to Roanoke flights
Midway to Greensboro flights
Midway to Richmond flights
Midway to Charlottesville flights
Midway to Roanoke flights
O'Hare Intl to Blountville flights
O'Hare Intl to Newport News flights
O'Hare Intl to Lewisburg flights
Midway to Blountville flights
O'Hare Intl to Salisbury flights
O'Hare Intl to Lynchburg flights
O'Hare Intl to Staunton flights
Midway to Newport News flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$238Average$382FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.