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Midway

$57+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Jul 14 — Jul 211
Mon 7/14
Mon 7/21
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 July 9, 2025.

Round-trip from

$223
(Southwest)

One-way from

$57
(Southwest)

Popular in

March

Cheapest in

August

Average price

$375
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. 1% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 9, 2025.

This Southwest deal was found by Cheapflights users on 7/6. 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.
Fri 10/35:35 amORF - MDW
Nonstop2h 10mSouthwest
Sun 10/58:35 pmMDW - ORF
Nonstop2h 00mSouthwest
Deal found 7/6$223
This Delta deal was found by Cheapflights users on 7/7. 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 9/46:00 amORF - MDW
1 stop3h 35mDelta
Sat 9/64:25 pmMDW - ORF
1 stop7h 00mDelta
Deal found 7/7$234
This Frontier deal was found by Cheapflights users on 7/8. 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.
Fri 8/224:12 pmORF - MDW
1 stop8h 15mFrontier
Fri 8/296:15 amMDW - ORF
1 stop8h 03mFrontier
Deal found 7/8$274
This Mytrip deal was found by Cheapflights users on 7/8. 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.
Thu 7/319:26 pmORF - MDW
2 stops17h 30mMultiple Airlines
Mon 8/41:11 pmMDW - ORF
3 stops26h 14mMultiple Airlines
Deal found 7/8$332

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 July 9, 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

Fri 10/3

5:35 am-6:45 am

Nonstop2h 10m

Chicago Midway

Sun 10/5

8:35 pm-11:35 pm

Nonstop2h 00m

$223

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 9/4

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Sat 9/6

4:25 pm-12:25 am

1 stop7h 00m

$234

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 8/22

4:12 pm-11:27 pm

1 stop8h 15m

Chicago Midway

Fri 8/29

6:15 am-3:18 pm

1 stop8h 03m

$274

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 7/31

9:26 pm-1:56 pm

2 stops17h 30m

Chicago Midway

Mon 8/4

1:11 pm-4:25 pm

3 stops26h 14m

$332

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 9/9

6:30 am-7:35 am

Nonstop2h 05m

$57

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 9/11

6:00 am-8:40 am

1 stop3h 40m

$99

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 8/29

4:12 pm-11:27 pm

1 stop8h 15m

$110

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sun 7/27

9:05 am-9:41 am

2 stops25h 36m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

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 July 9, 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 July 6, 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 July 9, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Allegiant Air 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
4,253 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.0

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.0

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
7,958 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.0

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
7.2
Good
705 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.0

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
5.9
Fair
3,268 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.0

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 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.

  • What are the cheapest airlines to fly from Virginia Beach to Chicago Midway Airport one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $57. However, be on the lookout for offers from Delta and Frontier, as they are both options that can get you from Virginia Beach to Chicago Midway Airport for a low price.

  • 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 $144 on average our data indicates $314 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 Virginia Beach?

Book flights to Virginia Beach if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
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 July 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$268Average$473FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$376FlexibilityNo cancel feeOn-time63%

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