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$73+ Cheap flights from Midway (MDW) to Virginia

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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Midway to Virginia

Keep the following information in mind while searching for Midway to Virginia flight deals. Data was last updated August 18, 2025.

Round-trip from

$139
(Southwest)

One-way from

$73
(Priceline)

Popular in

June

Cheapest in

September

Average price

$367

Good round-trip deal

$203 or less

Good one-way deal

$78 or less
From Chicago Midway to Virginia
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One-way flight from Chicago Midway to Virginia
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Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago Midway to Virginia.
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Price to beat on a one-way flight from Chicago Midway to Virginia.
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Find flight deals from Midway to Virginia

Cheapest flights from Midway to Virginia
Explore the most affordable flight options available from Midway to Virginia. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Southwest deal was found by Cheapflights users on 8/17. 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 9/233:00 pmMDW - RDU
Nonstop1h 50mSouthwest
Wed 9/246:00 pmRDU - MDW
Nonstop2h 00mSouthwest
Deal found 8/17$139
This Booking.com deal was found by Cheapflights users on 8/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/148:05 amMDW - IAD
1 stop10h 41mFrontier
Sat 10/184:22 pmIAD - MDW
1 stop8h 03mFrontier
Deal found 8/16$142
This Gotogate deal was found by Cheapflights users on 8/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/184:56 pmMDW - RDU
1 stop4h 54mFrontier
Mon 9/226:42 pmRDU - MDW
1 stop5h 38mFrontier
Deal found 8/17$143
This Flybillet deal was found by Cheapflights users on 8/17. 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 Flybillet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/44:56 pmMDW - IAD
1 stop6h 19mFrontier
Sun 9/71:55 pmIAD - MDW
1 stop10h 25mFrontier
Deal found 8/17$143
This Priceline deal was found by Cheapflights users on 8/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:15 pmMDW - RDU
1 stop4h 43mFrontier
Sun 9/286:38 pmRDU - MDW
1 stop5h 42mFrontier
Deal found 8/17$144
This Booking.com deal was found by Cheapflights users on 8/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:15 pmMDW - IAD
1 stop6h 00mFrontier
Mon 9/81:55 pmIAD - MDW
1 stop10h 25mFrontier
Deal found 8/17$144
This Gotogate deal was found by Cheapflights users on 8/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:20 amMDW - RDU
1 stop10h 18mFrontier
Sat 9/276:06 pmRDU - MDW
1 stop19h 38mFrontier
Deal found 8/16$148
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:20 amMDW - IAD
1 stop5h 35mFrontier
Sun 9/2810:09 pmIAD - MDW
1 stop15h 35mFrontier
Deal found 8/17$148
This Mytrip deal was found by Cheapflights users on 8/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2010:51 amMDW - RDU
1 stop6h 17mFrontier
Mon 9/226:42 pmRDU - MDW
1 stop5h 38mFrontier
Deal found 8/17$149
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/85:15 pmMDW - IAD
1 stop6h 00mFrontier
Fri 9/127:14 pmIAD - MDW
1 stop15h 37mFrontier
Deal found 8/17$149
This Booking.com deal was found by Cheapflights users on 8/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/410:51 amMDW - RDU
1 stop22h 02mFrontier
Mon 10/66:42 pmRDU - MDW
1 stop5h 38mFrontier
Deal found 8/17$150
This Booking.com deal was found by Cheapflights users on 8/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/146:21 amMDW - IAD
1 stop13h 58mFrontier
Sun 9/211:55 pmIAD - MDW
1 stop10h 25mFrontier
Deal found 8/15$150

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Virginia 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 August 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Virginia that are best for you.

Fly from

Midway

Fly to

Virginia

Route

Depart

Return

Price

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Tue 9/23

10:00 am-12:55 pm

Nonstop1h 55m

Raleigh-Durham

Wed 9/24

6:40 am-7:35 am

Nonstop1h 55m

$139

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Tue 10/14

8:05 am-7:46 pm

1 stop10h 41m

Washington, D.C. Dulles Intl

Sat 10/18

4:22 pm-11:25 pm

1 stop8h 03m

$142

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Thu 9/11

8:15 am-1:38 pm

1 stop4h 23m

Raleigh-Durham

Thu 9/18

6:38 pm-11:20 pm

1 stop5h 42m

$143

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Mon 9/15

8:15 am-1:38 pm

1 stop4h 23m

Raleigh-Durham

Mon 9/22

6:42 pm-11:20 pm

1 stop5h 38m

$143

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Thu 9/18

8:15 am-1:38 pm

1 stop4h 23m

Raleigh-Durham

Mon 9/22

6:42 pm-11:20 pm

1 stop5h 38m

$143

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Fri 9/19

5:15 pm-10:58 pm

1 stop4h 43m

Raleigh-Durham

Mon 9/22

6:42 pm-11:20 pm

1 stop5h 38m

$143

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Wed 10/15

8:05 am-3:37 pm

1 stop6h 32m

Raleigh-Durham

Fri 10/17

7:15 pm-11:25 pm

1 stop5h 10m

$143

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Thu 9/18

4:56 pm-10:50 pm

1 stop4h 54m

Raleigh-Durham

Thu 9/25

6:22 am-3:58 pm

1 stop10h 36m

$143

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Thu 9/4

8:15 am-1:38 pm

1 stop4h 23m

Raleigh-Durham

Sun 9/7

6:38 pm-11:20 pm

1 stop5h 42m

$143

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Thu 9/25

4:56 pm-10:50 pm

1 stop4h 54m

Raleigh-Durham

Thu 10/30

8:31 am-2:33 pm

1 stop7h 02m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Virginia

Have a flexible travel schedule? Discover the best time to fly to Virginia from Midway 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 Chicago Midway Airport to Virginia

What is the cheapest month to book a flight from Chicago Midway Airport to Virginia?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Virginia (average of $281). Flying from Chicago Midway Airport to Virginia in March is currently the most expensive (average of $351). 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 MDW to VA?

Find hourly flight availability from Midway to Virginia. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2025.

When flying from Chicago Midway Airport to Virginia, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Virginia

Get insights into the airlines that provide service to Virginia. 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 Virginia. Reviews last updated August 18, 2025.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to Virginia. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to Virginia. 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 Chicago Midway Airport to Virginia?

    Southwest, Frontier, and Delta can get you from Chicago Midway Airport to Virginia in just under 1h 55m. Your travel time can differ by up to 8h 46m. Chicago Midway Airport and Virginia are separated by a distance of 631 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Virginia one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $73. Southwest flights start at $89 while deals on Delta start at $144 one-way.

  • What are the most popular routes from Chicago Midway Airport to Virginia?

    When deciding which route to take from Chicago Midway Airport to Virginia consider Chicago Midway - Washington, D.C. Dulles Intl, Chicago Midway - Washington, D.C. Reagan-National or Chicago Midway - Richmond Byrd Intl as they are the most popular.

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

    On average you can expect to pay $152 for a flight from Chicago Midway Airport to Virginia. The cheapest flight overall is $74 while the most popular route, (Chicago Midway - Washington, D.C. Dulles Intl) is currently priced at $143.

  • Can I find deals for flights from Midway to Virginia that include hotel bookings?

    Yes. In addition to deals on Midway to Virginia flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Virginia?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Virginia.

  • Can I find deals for business class flights from Midway to Virginia?

    Yes. Cheapflights offers flight deals from Midway to Virginia 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 Chicago Midway Airport to Virginia?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Virginia (average of $281). Flying from Chicago Midway Airport to Virginia in March is currently the most expensive (average of $351). 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

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Alternative routes for Midway to Virginia

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Midway to Virginia

Discover the top airline that operate flights from Midway to Virginia. 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$213Average$370FlexibilityNo cancel feeOn-time63%

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