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Midway

$70+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Apr 19 — Apr 261
Sun 4/19
Sun 4/26
1 adult, Economy
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Cheap 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 March 20, 2026.

This Frontier deal was found by Cheapflights users on 3/17. 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.
Thu 4/1611:27 am
ORF
-
MDW
1 stop9h 04m
Frontier
Mon 4/209:14 am
MDW
-
ORF
1 stop6h 53m
Frontier
Deal found 3/17$280
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 5/111:27 am
ORF
-
MDW
1 stop9h 04m
Multiple Airlines
Thu 5/76:00 am
MDW
-
ORF
2 stops13h 17m
Multiple Airlines
Deal found 3/17$290
This Southwest deal was found by Cheapflights users on 3/17. 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 6/47:15 pm
ORF
-
MDW
Nonstop2h 05m
Southwest
Mon 6/87:00 pm
MDW
-
ORF
Nonstop2h 00m
Southwest
Deal found 3/17$297
This Expedia deal was found by Cheapflights users on 3/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:12 pm
ORF
-
MDW
1 stop22h 48m
Frontier
Mon 4/209:14 am
MDW
-
ORF
1 stop6h 53m
Frontier
Deal found 3/19$301
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Wed 4/17:05 am
ORF
-
MDW
1 stop15h 53m
Multiple Airlines
Sun 4/55:05 am
MDW
-
ORF
1 stop15h 42m
Multiple Airlines
Deal found 3/18$305
This Southwest deal was found by Cheapflights users on 3/16. 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 4/117:55 am
ORF
-
MDW
Nonstop2h 05m
Southwest
Wed 4/157:00 am
MDW
-
ORF
1 stop3h 55m
Southwest
Deal found 3/16$307
This Southwest deal was found by Cheapflights users on 3/18. 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 5/136:25 pm
ORF
-
MDW
Nonstop2h 10m
Southwest
Sat 5/167:50 am
MDW
-
ORF
Nonstop2h 00m
Southwest
Deal found 3/18$310
This Southwest deal was found by Cheapflights users on 3/17. 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 4/146:25 pm
ORF
-
MDW
Nonstop2h 10m
Southwest
Tue 4/2112:45 pm
MDW
-
ORF
2 stops8h 10m
Southwest
Deal found 3/17$312
This Delta deal was found by Cheapflights users on 3/17. 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 6/46:00 am
ORF
-
MDW
1 stop3h 43m
Delta
Mon 6/85:59 pm
MDW
-
ORF
1 stop4h 34m
Delta
Deal found 3/17$317
This Southwest deal was found by Cheapflights users on 3/16. 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 4/187:55 am
ORF
-
MDW
Nonstop2h 05m
Southwest
Mon 4/207:00 pm
MDW
-
ORF
Nonstop2h 00m
Southwest
Deal found 3/16$320
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/2411:27 am
ORF
-
MDW
1 stop11h 59m
Multiple Airlines
Mon 4/276:00 am
MDW
-
ORF
2 stops15h 51m
Multiple Airlines
Deal found 3/17$321

Find 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 March 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$280
(Frontier)

One-way from

$70
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$509
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
Search Deals
From Virginia Beach to Chicago Midway
Search Deals
One-way flight from Virginia Beach to Chicago Midway
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 20, 2026.
Use the filters below to find and compare flights from Virginia Beach to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 4/16

10:05 am-3:05 pm

1 stop6h 00m

Chicago Midway

Mon 4/20

7:00 pm-10:00 pm

Nonstop2h 00m

$307
Quickest round-trip

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 4/18

7:55 am-9:00 am

Nonstop2h 05m

Chicago Midway

Mon 4/20

7:00 pm-10:00 pm

Nonstop2h 00m

$320

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 4/25

8:40 am-1:10 pm

1 stop5h 30m

Chicago Midway

Sat 4/25

2:15 pm-11:05 pm

2 stops7h 50m

$322

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 4/17

10:05 am-8:05 pm

2 stops11h 00m

Chicago Midway

Mon 4/20

3:50 pm-10:55 pm

2 stops6h 05m

$353

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 6/13

6:35 pm-7:40 pm

Nonstop2h 05m

Chicago Midway

Mon 6/15

7:00 pm-10:00 pm

Nonstop2h 00m

$365

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 4/30

10:05 am-3:05 pm

1 stop6h 00m

Chicago Midway

Sun 5/3

7:05 pm-10:05 pm

Nonstop2h 00m

$366

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 9/4

8:00 am-9:00 am

Nonstop2h 00m

Chicago Midway

Mon 9/7

6:50 pm-9:55 pm

Nonstop2h 05m

$373

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 6/4

4:39 pm-9:09 pm

1 stop5h 30m

Chicago Midway

Mon 6/8

5:25 pm-12:04 am

1 stop5h 39m

$377

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 8/13

6:25 am-1:45 pm

2 stops8h 20m

Chicago Midway

Mon 8/24

9:00 am-12:10 pm

Nonstop2h 10m

$380

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 7/28

5:50 am-8:42 am

1 stop3h 52m

Chicago Midway

Thu 8/13

10:35 am-5:05 pm

1 stop5h 30m

$385

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/16

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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, February is the cheapest month in which you can book a flight from Virginia Beach to Chicago Midway Airport (average of $152). Flying from Virginia Beach to Chicago Midway Airport in July is currently the most expensive (average of $349). 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 March 20, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 16% on flights from Virginia Beach to Chicago Midway Airport by exploring options for tickets at noon.

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 14, 2026.

Travelers seeking maximum savings on their Virginia Beach to Chicago Midway Airport flight should consider departing on Saturday at noon 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 March 20, 2026.
Peruse reviews from past customers who have flown with Southwest and Frontier 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
4,320 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,320 reviews
Southwest
8.0
Very good
4,320 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,024 reviews
Southwest
8.0
Very good
4,320 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 6h. 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 $93. While the most popular route (Norfolk - Chicago Midway) can be booked for $225 on average, our data indicates $350 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, February is the cheapest month in which you can book a flight from Virginia Beach to Chicago Midway Airport (average of $152). Flying from Virginia Beach to Chicago Midway Airport in July is currently the most expensive (average of $349). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 March 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$154Average$340FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$362FlexibilityNo cancel feeOn-time63%

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