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Midway

$63+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Frontier deal was found by Cheapflights users on 1/27. 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 2/2311:39 am
ORF
-
MDW
1 stop9h 08m
Frontier
Thu 2/267:30 am
MDW
-
ORF
1 stop9h 58m
Frontier
Deal found 1/27$148
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/611:43 am
ORF
-
MDW
1 stop22h 00m
Multiple Airlines
Mon 2/95:01 pm
MDW
-
ORF
2 stops24h 37m
Multiple Airlines
Deal found 1/27$158
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/611:43 am
ORF
-
MDW
1 stop22h 00m
Frontier
Mon 2/91:00 pm
MDW
-
ORF
1 stop22h 05m
Frontier
Deal found 1/27$164
This Frontier deal was found by Cheapflights users on 1/27. 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 3/211:39 am
ORF
-
MDW
1 stop11h 50m
Frontier
Sat 3/76:15 am
MDW
-
ORF
1 stop7h 16m
Frontier
Deal found 1/27$173
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/216:45 am
ORF
-
MDW
1 stop9h 10m
Multiple Airlines
Sat 2/289:15 am
MDW
-
ORF
2 stops11h 35m
Multiple Airlines
Deal found 1/27$174
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/511:43 am
ORF
-
MDW
1 stop11h 36m
Frontier
Sun 2/85:01 pm
MDW
-
ORF
1 stop16h 47m
Frontier
Deal found 1/28$175
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/611:43 am
ORF
-
MDW
1 stop22h 00m
Frontier
Sun 2/85:01 pm
MDW
-
ORF
1 stop16h 47m
Frontier
Deal found 1/28$179
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/2011:32 am
ORF
-
MDW
1 stop7h 21m
Frontier
Sun 2/226:00 am
MDW
-
ORF
1 stop27h 42m
Frontier
Deal found 1/27$181
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/2011:32 am
ORF
-
MDW
1 stop11h 53m
Frontier
Mon 2/239:22 pm
MDW
-
ORF
1 stop13h 43m
Frontier
Deal found 1/27$195
This Frontier deal was found by Cheapflights users on 1/27. 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 3/511:46 am
ORF
-
MDW
1 stop11h 43m
Frontier
Sat 3/76:15 am
MDW
-
ORF
1 stop7h 16m
Frontier
Deal found 1/27$198
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/277:31 pm
ORF
-
MDW
2 stops20h 48m
Multiple Airlines
Sun 3/19:04 pm
MDW
-
ORF
1 stop12h 38m
Multiple Airlines
Deal found 1/27$204

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$148
(Frontier)

One-way from

$63
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$407
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. 5% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
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 2/23

11:39 am-7:47 pm

1 stop9h 08m

Chicago Midway

Thu 2/26

7:30 am-6:28 pm

1 stop9h 58m

$175

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 3/14

6:45 am-1:08 pm

1 stop7h 23m

Chicago Midway

Mon 3/16

7:25 am-10:32 pm

1 stop14h 07m

$216

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 2/20

11:32 am-5:53 pm

1 stop7h 21m

Chicago Midway

Sun 2/22

9:04 pm-6:26 pm

2 stops20h 22m

$264

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 2/21

5:25 am-10:21 am

1 stop5h 56m

Chicago Midway

Wed 2/25

6:40 pm-12:14 am

1 stop4h 34m

$281

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 3/11

10:57 am-5:22 pm

1 stop7h 25m

Chicago Midway

Sat 3/14

9:35 am-4:07 pm

1 stop5h 32m

$287

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 4/7

5:45 am-8:53 am

1 stop4h 08m

Chicago Midway

Sat 4/11

6:34 pm-12:31 am

1 stop4h 57m

$287

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 3/4

5:35 pm-6:50 pm

Nonstop2h 15m

Chicago Midway

Mon 3/9

5:00 pm-11:35 pm

1 stop5h 35m

$289

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 3/14

7:20 pm-8:35 pm

Nonstop2h 15m

Chicago Midway

Mon 3/16

3:45 pm-10:55 pm

1 stop6h 10m

$292

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 4/17

6:43 pm-7:31 pm

2 stops25h 48m

Chicago Midway

Mon 4/20

9:14 am-10:59 pm

1 stop12h 45m

$301

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 4/27

11:19 am-10:19 pm

1 stop12h 00m

$96

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 21 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 January is currently the most expensive (average of $353). 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 January 29, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 14% 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 January 24, 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 January 29, 2026.
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
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 5h 56m. Fly via Frontier or Delta to get the fastest option. Virginia Beach and Chicago Midway Airport are separated by a distance of 702 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Looking at all options, your cheapest flight can be booked for $163. While the most popular route (Norfolk - Chicago Midway) can be booked for $158 on average, our data indicates $357 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 January is currently the most expensive (average of $353). 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

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$178Average$363FlexibilityNo cancel feeOn-time63%

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