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Midway

$59+ Cheap flights from Virginia Beach, VA to Midway (MDW)

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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Virginia Beach to Midway

Keep the following information in mind while searching for Virginia Beach to Midway flight deals. Data was last updated September 11, 2025.

Round-trip from

$219
(Southwest)

One-way from

$59
(Southwest)

Popular in

March

Cheapest in

September

Average price

$306
From Virginia Beach to Chicago Midway
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One-way flight from Virginia Beach to Chicago Midway
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Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Virginia Beach to Midway

Cheapest flights from Virginia Beach to Midway
Explore the most affordable flight options available from Virginia Beach to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/159:45 amORF - MDW
2 stops8h 05mSouthwest
Sat 10/188:20 amMDW - ORF
2 stops5h 40mSouthwest
Deal found 9/10$219
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/111:45 amORF - MDW
1 stop5h 40mSouthwest
Sat 10/410:00 amMDW - ORF
2 stops12h 00mSouthwest
Deal found 9/10$220
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:00 amORF - MDW
2 stops17h 41mMultiple Airlines
Sun 10/510:13 amMDW - ORF
1 stop5h 44mMultiple Airlines
Deal found 9/11$222
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:01 amORF - MDW
1 stop15h 19mMultiple Airlines
Sun 11/910:12 amMDW - ORF
1 stop12h 55mMultiple Airlines
Deal found 9/11$228
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:10 pmORF - MDW
Nonstop2h 10mSouthwest
Tue 10/215:35 amMDW - ORF
1 stop4h 30mSouthwest
Deal found 9/10$229
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/133:20 pmORF - MDW
1 stop7h 43mMultiple Airlines
Sat 11/156:15 amMDW - ORF
2 stops16h 25mMultiple Airlines
Deal found 9/9$232
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:10 pmORF - MDW
Nonstop2h 10mSouthwest
Wed 10/227:35 amMDW - ORF
2 stops7h 20mSouthwest
Deal found 9/10$235
This Southwest deal was found by Cheapflights users on 9/11. 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.
Tue 10/2111:15 amORF - MDW
1 stop8h 05mSouthwest
Fri 10/247:00 pmMDW - ORF
Nonstop2h 00mSouthwest
Deal found 9/11$239
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/275:38 pmORF - MDW
1 stop16h 40mMultiple Airlines
Thu 10/24:56 pmMDW - ORF
1 stop17h 28mMultiple Airlines
Deal found 9/11$243

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia Beach to Midway 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 September 11, 2025.
Use the filters below to find and compare flights from Virginia Beach to Chicago Midway Airport that are best for you.

Fly from

Virginia Beach

Fly to

Midway

Route

Depart

Return

Price

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 10/15

9:45 am-4:50 pm

2 stops8h 05m

Chicago Midway

Sat 10/18

8:20 am-3:00 pm

2 stops5h 40m

$219

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 10/21

6:25 pm-7:35 pm

Nonstop2h 10m

Chicago Midway

Fri 10/24

7:00 pm-10:00 pm

Nonstop2h 00m

$229

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 10/16

7:10 pm-8:20 pm

Nonstop2h 10m

Chicago Midway

Wed 10/22

6:05 pm-9:05 pm

Nonstop2h 00m

$236

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 10/1

6:00 pm-7:10 pm

Nonstop2h 10m

Chicago Midway

Sat 10/4

5:45 am-2:40 pm

1 stop7h 55m

$254

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 11/13

5:30 am-6:40 am

Nonstop2h 10m

Chicago Midway

Sun 11/16

7:45 am-3:35 pm

1 stop6h 50m

$264

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 10/30

7:10 pm-8:20 pm

Nonstop2h 10m

Chicago Midway

Sun 11/2

5:15 am-3:35 pm

1 stop9h 20m

$264

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 3/3

5:45 am-8:50 am

1 stop4h 05m

Chicago Midway

Wed 3/4

9:30 am-10:55 pm

2 stops12h 25m

$277

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 10/13

6:10 am-1:20 pm

2 stops8h 10m

Chicago Midway

Wed 10/15

6:05 pm-9:05 pm

Nonstop2h 00m

$289

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 12/9

5:30 pm-6:40 pm

Nonstop2h 10m

$59

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 10/15

6:25 pm-7:35 pm

Nonstop2h 10m

$59

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 18 results
1
2

Best time to book a flight from Virginia Beach to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Virginia Beach 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 Virginia Beach to Chicago Midway Airport

What is the cheapest month to book a flight from Virginia Beach to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Virginia Beach to Chicago Midway Airport (average of $160). Flying from Virginia Beach to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 V1B to MDW?

Find hourly flight availability from Virginia Beach to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Virginia Beach to Chicago Midway Airport as you normally would.

What is the cheapest day to fly from Virginia Beach to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Virginia Beach to Midway. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their Virginia Beach to Chicago Midway Airport flight should consider departing on Saturday afternoons when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 11, 2025.
Peruse reviews from past customers who have flown with Southwest from Virginia Beach to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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 Virginia Beach to Midway. 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 Virginia Beach to Chicago Midway Airport?

    There are many flights that can get you from Virginia Beach to Chicago Midway Airport in 8h 05m. Fly via Southwest to get the fastest option. Virginia Beach and Chicago Midway Airport are separated by a distance of 702 mi.

  • What are the cheapest flights from Virginia Beach to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $108. While the most popular route (Norfolk - Chicago Midway) can be booked for $160 on average, our data indicates $281 when flying from Virginia Beach to Chicago Midway Airport.

  • Can I find deals for flights from Virginia Beach to Midway that include hotel bookings?

    Yes. In addition to deals on Virginia Beach to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Virginia Beach to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Virginia Beach to Midway.

  • Can I find deals for business class flights from Virginia Beach to Midway?

    Yes. Cheapflights offers flight deals from Virginia Beach to Midway 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 Virginia Beach to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Virginia Beach to Chicago Midway Airport (average of $160). Flying from Virginia Beach to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Virginia Beach to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Virginia Beach to Midway

Discover the top 2 airlines that operate flights from Virginia Beach to Midway. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$257Average$383FlexibilityNo cancel feeOn-time63%
DeltaCheapest$320Average$487FlexibilityNo cancel feeOn-timeN/A

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