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$71+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$143
(Cheapflightsfares)

One-way from

$71
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$343

Good round-trip deal

$281 or less

Good one-way deal

$149 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. 2% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1611:49 amMDW - RDU
1 stop5h 19mFrontier
Sun 10/197:15 pmRDU - MDW
1 stop5h 31mFrontier
Deal found 9/13$143
This CheapOair deal was found by Cheapflights users on 9/13. 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.
Fri 10/39:48 amMDW - IAD
1 stop7h 31mFrontier
Mon 10/66:10 amIAD - MDW
1 stop11h 15mFrontier
Deal found 9/13$143
This Priceline deal was found by Cheapflights users on 9/14. 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 10/39:48 amMDW - RDU
1 stop7h 20mFrontier
Mon 10/131:51 pmRDU - MDW
1 stop10h 55mFrontier
Deal found 9/14$144
This Flightnetwork deal was found by Cheapflights users on 9/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1811:31 amMDW - IAD
1 stop8h 22mFrontier
Mon 10/204:45 pmIAD - MDW
1 stop8h 01mFrontier
Deal found 9/14$144
This Booking.com deal was found by Cheapflights users on 9/14. 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.
Thu 9/258:15 amMDW - RDU
1 stop4h 23mFrontier
Sat 9/276:06 pmRDU - MDW
1 stop19h 38mFrontier
Deal found 9/14$145
This Flightnetwork deal was found by Cheapflights users on 9/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/249:00 amMDW - IAD
1 stop9h 55mFrontier
Thu 9/251:55 pmIAD - MDW
1 stop10h 25mFrontier
Deal found 9/14$145
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:21 amMDW - RDU
1 stop9h 50mFrontier
Tue 9/306:45 amRDU - MDW
1 stop10h 13mFrontier
Deal found 9/15$146
This Booking.com deal was found by Cheapflights users on 9/13. 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.
Thu 10/24:56 pmMDW - IAD
1 stop5h 43mFrontier
Sun 10/57:14 pmIAD - MDW
1 stop13h 09mFrontier
Deal found 9/13$146
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 12/76:00 amMDW - IAD
1 stop5h 49mFrontier
Wed 12/108:00 amIAD - MDW
1 stop14h 32mFrontier
Deal found 9/14$147
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:30 amMDW - RDU
1 stop9h 19mFrontier
Mon 10/137:15 pmRDU - MDW
1 stop5h 31mFrontier
Deal found 9/16$148
This Booking.com deal was found by Cheapflights users on 9/15. 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.
Thu 9/256:20 amMDW - IAD
1 stop5h 35mFrontier
Mon 9/296:10 amIAD - MDW
1 stop10h 50mFrontier
Deal found 9/15$149
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/510:13 amMDW - RDU
1 stop22h 40mFrontier
Wed 10/86:30 amRDU - MDW
1 stop28h 17mFrontier
Deal found 9/15$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 September 16, 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

Sat 9/27

10:51 am-6:08 pm

1 stop6h 17m

Raleigh-Durham

Mon 9/29

6:42 pm-11:20 pm

1 stop5h 38m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 10/3

5:15 pm-11:39 pm

1 stop5h 24m

Washington, D.C. Dulles Intl

Wed 10/8

9:00 am-1:38 pm

1 stop5h 38m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 10/4

11:21 am-6:29 pm

1 stop6h 08m

Washington, D.C. Dulles Intl

Mon 10/6

1:55 pm-11:41 pm

1 stop10h 46m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 10/3

5:15 pm-11:39 pm

1 stop5h 24m

Washington, D.C. Dulles Intl

Sat 10/4

7:14 pm-9:18 am

1 stop15h 04m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 10/17

5:28 pm-8:53 pm

1 stop26h 25m

Washington, D.C. Dulles Intl

Mon 10/20

4:45 pm-11:46 pm

1 stop8h 01m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 10/31

1:37 pm-11:29 pm

1 stop8h 52m

Washington, D.C. Dulles Intl

Sun 11/2

8:36 pm-8:32 am

1 stop12h 56m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sun 11/16

1:37 pm-12:11 am

1 stop9h 34m

Washington, D.C. Dulles Intl

Wed 11/19

8:40 am-12:41 pm

1 stop5h 01m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Mon 11/3

6:20 am-5:23 pm

1 stop10h 03m

Washington, D.C. Dulles Intl

Wed 11/5

8:40 am-12:41 pm

1 stop5h 01m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 9/26

6:21 am-8:09 pm

1 stop12h 48m

Washington, D.C. Dulles Intl

Tue 9/30

9:15 am-3:58 pm

1 stop7h 43m

$143

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 10/25

6:15 am-3:17 pm

1 stop8h 02m

Washington, D.C. Dulles Intl

Mon 10/27

5:00 pm-11:46 pm

1 stop7h 46m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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 September 16, 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 September 16, 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
4,242 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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 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?

    Frontier, Southwest, and Delta can get you from Chicago Midway Airport to Virginia in just under 5h 30m. Your travel time can differ by up to 1h 02m. 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 $78. Southwest flights start at $89 while deals on Delta start at $125 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 - Raleigh-Durham as they are the most popular.

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

    On average you can expect to pay $342 for a flight from Chicago Midway Airport to Virginia. The cheapest flight overall is $78 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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Midway to Miami flights
O'Hare Intl to Love Field flights
Midway to Seattle flights
Midway to Denver flights
O'Hare Intl to George Bush Intcntl flights

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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$213Average$369FlexibilityNo cancel feeOn-time63%

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