HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$95+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Virginia Beach to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 30, 2025.

Round-trip from

$237
(Delta)

One-way from

$95
(Frontier)

Popular in

March

Cheapest in

August

Average price

$375
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. 2% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 30, 2025.

This Southwest deal was found by Cheapflights users on 7/30. 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.
Thu 9/46:15 pmORF - MDW
Nonstop2h 05mSouthwest
Tue 9/96:20 pmMDW - ORF
Nonstop2h 05mSouthwest
Deal found 7/30$239
This Frontier deal was found by Cheapflights users on 7/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/14:12 pmORF - MDW
1 stop8h 15mFrontier
Sun 9/710:13 amMDW - ORF
1 stop5h 44mFrontier
Deal found 7/28$258
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:00 amORF - MDW
1 stop3h 40mDelta
Mon 10/69:35 amMDW - ORF
1 stop5h 47mDelta
Deal found 7/29$259

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 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

Thu 9/4

6:15 pm-7:20 pm

Nonstop2h 05m

Chicago Midway

Tue 9/9

6:20 pm-9:25 pm

Nonstop2h 05m

$239

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 9/1

4:12 pm-11:27 pm

1 stop8h 15m

Chicago Midway

Sun 9/7

10:13 am-4:57 pm

1 stop5h 44m

$258

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 9/27

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Mon 10/6

9:35 am-4:22 pm

1 stop5h 47m

$259

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 10/15

3:27 pm-10:58 pm

1 stop8h 31m

$95

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 9/10

6:00 pm-7:10 pm

Nonstop2h 10m

$109

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 9/10

5:30 am-9:34 am

1 stop5h 04m

$119

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sun 8/3

3:54 pm-1:56 pm

2 stops23h 02m

$211

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 9/25

5:38 pm-8:52 pm

3 stops28h 14m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 30, 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 27, 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 30, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, 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
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,237 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $95. However, be on the lookout for offers from Southwest and Delta, 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 $53. While the most popular route (Norfolk - Chicago Midway) can be booked for $208 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, 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Virginia Beach to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Reagan-National to Midway flights
Richmond to O'Hare Intl flights
Raleigh to Midway flights
Norfolk to O'Hare Intl flights
Greensboro to O'Hare Intl flights
Roanoke to O'Hare Intl flights
Richmond to Midway flights
Charlottesville to O'Hare Intl flights
Greensboro to Midway flights
Norfolk to Midway flights
Roanoke to Midway flights
Blountville to O'Hare Intl flights
Charlottesville to Midway flights
Blountville to Midway flights
Lewisburg to O'Hare Intl flights
Staunton to O'Hare Intl flights
Lynchburg to O'Hare Intl flights
Newport News to O'Hare Intl flights
Raleigh to Rockford flights
Salisbury to O'Hare Intl flights
Norfolk to Rockford flights
Newport News to Midway flights
Richmond to Rockford flights

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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$231Average$374FlexibilityNo cancel feeOn-time63%
DeltaCheapest$298Average$487FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.