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Midway

$55+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:40 pmORF - MDW
1 stop5h 32mMultiple Airlines
Wed 12/246:12 amMDW - ORF
2 stops30h 54mMultiple Airlines
Deal found 10/30$200
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:00 pmORF - MDW
1 stop11h 12mMultiple Airlines
Wed 12/246:12 amMDW - ORF
2 stops30h 54mMultiple Airlines
Deal found 10/30$204
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/268:02 pmORF - MDW
2 stops27h 41mMultiple Airlines
Mon 12/15:47 pmMDW - ORF
1 stop25h 44mMultiple Airlines
Deal found 10/29$207
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:40 pmORF - MDW
1 stop16h 06mFrontier
Thu 12/186:33 pmMDW - ORF
1 stop18h 06mFrontier
Deal found 10/30$208
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/139:03 pmORF - MDW
1 stop26h 07mMultiple Airlines
Mon 11/176:06 pmMDW - ORF
1 stop20h 35mMultiple Airlines
Deal found 10/30$210
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:00 pmORF - MDW
1 stop11h 12mFrontier
Thu 12/186:33 pmMDW - ORF
1 stop18h 06mFrontier
Deal found 10/30$212
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:40 pmORF - MDW
1 stop5h 32mFrontier
Mon 12/226:12 amMDW - ORF
1 stop5h 57mFrontier
Deal found 10/30$213
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/58:11 pmORF - MDW
2 stops18h 48mMultiple Airlines
Sun 12/76:37 pmMDW - ORF
1 stop12h 06mMultiple Airlines
Deal found 10/29$216
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:00 pmORF - MDW
1 stop11h 12mFrontier
Mon 12/226:12 amMDW - ORF
1 stop5h 57mFrontier
Deal found 10/30$218
This Frontier deal was found by Cheapflights users on 10/30. 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.
Mon 11/1711:29 amORF - MDW
1 stop11h 42mFrontier
Mon 11/246:05 amMDW - ORF
1 stop8h 16mFrontier
Deal found 10/30$230
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/126:33 pmORF - MDW
1 stop15h 39mMultiple Airlines
Mon 11/179:27 amMDW - ORF
1 stop11h 35mMultiple Airlines
Deal found 10/29$234

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$207
(Kiwi.com)

One-way from

$55
(Priceline)

Popular in

March

Cheapest in

September

Average price

$354
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. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 30, 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

Mon 12/15

5:40 pm-8:46 am

1 stop16h 06m

Chicago Midway

Thu 12/18

6:33 pm-1:39 pm

1 stop18h 06m

$208

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 11/12

6:33 pm-9:12 am

1 stop15h 39m

Chicago Midway

Mon 11/17

9:27 am-10:02 pm

1 stop11h 35m

$234

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 11/25

3:50 pm-10:03 pm

1 stop7h 13m

Chicago Midway

Sun 11/30

5:30 pm-9:43 am

1 stop15h 13m

$268

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 11/14

7:00 am-4:57 pm

1 stop10h 57m

Chicago Midway

Sun 11/16

6:06 pm-6:58 pm

2 stops23h 52m

$283

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 12/30

7:40 pm-9:58 pm

1 stop27h 18m

Chicago Midway

Sat 1/3

6:12 am-4:27 pm

1 stop9h 15m

$293

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 3/3

5:45 am-8:50 am

1 stop4h 05m

Chicago Midway

Wed 3/4

1:05 pm-8:05 pm

1 stop6h 00m

$295

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 11/24

5:40 am-8:54 am

1 stop4h 14m

Chicago Midway

Wed 12/3

10:49 am-6:34 pm

1 stop6h 45m

$296

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 11/27

5:45 am-6:55 am

Nonstop2h 10m

Chicago Midway

Thu 12/4

8:50 am-4:45 pm

1 stop6h 55m

$305

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 11/13

3:20 pm-10:03 pm

1 stop7h 43m

Chicago Midway

Sun 11/16

6:06 pm-10:18 pm

1 stop27h 12m

$306

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 12/6

6:10 am-2:05 pm

2 stops8h 55m

Chicago Midway

Mon 12/8

6:05 pm-9:05 pm

Nonstop2h 00m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 24 results
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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, September is the cheapest month in which you can book a flight from Virginia Beach to Chicago Midway Airport (average of $175). Flying from Virginia Beach to Chicago Midway Airport in December is currently the most expensive (average of $366). 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 October 30, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 19% on flights from Virginia Beach to Chicago Midway Airport by exploring options for tickets in the afternoon.

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 October 26, 2025.

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 October 30, 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
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

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 16h 06m. Fly via Frontier 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 $78. While the most popular route (Norfolk - Chicago Midway) can be booked for $139 on average, our data indicates $327 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, September is the cheapest month in which you can book a flight from Virginia Beach to Chicago Midway Airport (average of $175). Flying from Virginia Beach to Chicago Midway Airport in December is currently the most expensive (average of $366). 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
Porter
Benton Harbor

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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 airline flying from Virginia Beach to Midway

Discover the top airline 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$229Average$381FlexibilityNo cancel feeOn-time63%

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