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$99+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$228
(Frontier)

One-way from

$99
(Frontier)

Popular in

April

Cheapest in

August

Average price

$444
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
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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. 11% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Frontier deal was found by Cheapflights users on 4/30. 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.
Sat 5/315:12 pmORF - MDW
1 stop6h 05mFrontier
Mon 6/27:05 amMDW - ORF
1 stop8h 11mFrontier
Deal found 4/30$228
This Southwest deal was found by Cheapflights users on 4/30. 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 5/216:15 amORF - MDW
Nonstop2h 10mSouthwest
Sat 5/2412:45 pmMDW - ORF
Nonstop2h 00mSouthwest
Deal found 4/30$285
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 5/315:35 amORF - MDW
1 stop5h 05mDelta
Sat 5/314:15 pmMDW - ORF
1 stop6h 09mDelta
Deal found 4/30$322
This Mytrip deal was found by Cheapflights users on 4/30. 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 6/512:13 pmORF - MDW
3 stops32h 33mMultiple Airlines
Mon 6/98:05 amMDW - ORF
3 stops32h 29mMultiple Airlines
Deal found 4/30$456

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 May 1, 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

Sat 5/31

5:12 pm-10:17 pm

1 stop6h 05m

Chicago Midway

Mon 6/2

7:05 am-4:16 pm

1 stop8h 11m

$228

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 5/21

6:15 am-7:25 am

Nonstop2h 10m

Chicago Midway

Sat 5/24

12:45 pm-3:45 pm

Nonstop2h 00m

$285

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 5/31

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

Sat 5/31

4:15 pm-11:24 pm

1 stop6h 09m

$322

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 6/5

12:13 pm-7:46 pm

3 stops32h 33m

Chicago Midway

Mon 6/9

8:05 am-5:34 pm

3 stops32h 29m

$456

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 5/28

5:12 pm-10:36 pm

1 stop6h 24m

$99

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 7/1

7:25 pm-8:35 pm

Nonstop2h 10m

$133

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 6/5

11:35 am-7:46 pm

2 stops33h 11m

$138

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 7/30

6:00 am-8:39 am

1 stop3h 39m

$143

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 6/12

4:14 pm-7:46 pm

2 stops28h 32m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 May 1, 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 March 30, 2025.

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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 Frontier, with whom users have recently found tickets for as low as $99. However, be on the lookout for offers from Southwest and Allegiant Air, 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 $126. While the most popular route (Norfolk - Chicago Midway) can be booked for $261 on average our data indicates $331 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
Hammond
Benton Harbor
Porter
Lansing
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$176Average$511FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$380FlexibilityNo cancel feeOn-time63%

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