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Isle of Wight

$100+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$240
(CheapOair)

One-way from

$100
(CheapOair)

Popular in

May

Cheapest in

November

Average price

$405
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. 17% potential increase in price ($94 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 28, 2025.

This CheapOair deal was found by Cheapflights users on 3/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1012:46 pmMDW - ORF
1 stop26h 45mFrontier
Tue 4/153:31 pmORF - MDW
1 stop5h 14mFrontier
Deal found 3/25$240
This Southwest deal was found by Cheapflights users on 3/26. 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 5/15:45 amMDW - ORF
1 stop3h 35mSouthwest
Tue 5/66:15 amORF - MDW
Nonstop2h 10mSouthwest
Deal found 3/26$315
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2212:48 pmMDW - ORF
1 stop4h 14mDelta
Mon 4/285:51 pmORF - MDW
1 stop5h 31mDelta
Deal found 3/27$325
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Sun 7/2711:37 amMDW - ORF
2 stops32h 25mAllegiant Air
Sun 8/33:54 pmORF - MDW
2 stops23h 02mAllegiant Air
Deal found 3/25$415

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 March 28, 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 4/10

12:46 pm-4:31 pm

1 stop26h 45m

Norfolk

Tue 4/15

3:31 pm-7:45 pm

1 stop5h 14m

$240

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 5/1

5:45 am-10:20 am

1 stop3h 35m

Norfolk

Tue 5/6

6:15 am-7:25 am

Nonstop2h 10m

$315

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 4/22

12:48 pm-6:02 pm

1 stop4h 14m

Norfolk

Mon 4/28

5:51 pm-10:22 pm

1 stop5h 31m

$325

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sun 7/27

11:37 am-9:02 pm

2 stops32h 25m

Norfolk

Sun 8/3

3:54 pm-1:56 pm

2 stops23h 02m

$415

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sun 5/4

8:30 am-3:51 pm

1 stop6h 21m

$100

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 4/30

6:35 pm-9:35 pm

Nonstop2h 00m

$153

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mon 6/16

8:36 pm-9:54 pm

2 stops24h 18m

$156

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mon 4/28

4:59 pm-12:12 am

1 stop6h 13m

$163

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sun 6/15

11:45 am-8:59 pm

2 stops32h 14m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 June is currently the most expensive (average of $372). 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 March 28, 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 30, 2024.

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. Saturday at noon 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 March 28, 2025.
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,271 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $100. 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 $358 for a flight from Chicago Midway Airport to Isle of Wight. The cheapest flight overall is $212 while the most popular route, (Chicago Midway - Norfolk) is currently priced at $250.

  • 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 June is currently the most expensive (average of $372). 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 2 airlines flying from Midway to Isle of Wight

Discover the top 2 airlines 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$123Average$384FlexibilityNo cancel feeOn-time63%
DeltaCheapest$346Average$605FlexibilityNo cancel feeOn-timeN/A
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