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$56+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap 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 December 8, 2025.

This CheapOair deal was found by Cheapflights users on 12/7. 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.
Tue 12/162:49 pmMDW - RDU
1 stop8h 23mFrontier
Tue 12/236:14 pmRDU - MDW
1 stop21h 23mFrontier
Deal found 12/7$163
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/186:12 amMDW - IAD
1 stop11h 04mFrontier
Fri 1/95:41 pmIAD - MDW
1 stop5h 40mFrontier
Deal found 12/7$163
This Super.com deal was found by Cheapflights users on 12/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - RDU
1 stop16h 18mFrontier
Thu 1/112:55 pmRDU - MDW
1 stop5h 43mFrontier
Deal found 12/7$169
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/186:12 amMDW - IAD
1 stop11h 04mFrontier
Thu 1/15:35 amIAD - MDW
1 stop13h 03mFrontier
Deal found 12/7$174
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/146:37 pmMDW - IAD
2 stops19h 33mMultiple Airlines
Mon 12/156:58 pmIAD - MDW
1 stop14h 48mMultiple Airlines
Deal found 12/6$175
This CheapOair deal was found by Cheapflights users on 12/6. 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.
Sat 12/132:59 pmMDW - IAD
1 stop19h 10mFrontier
Mon 1/124:22 pmIAD - MDW
1 stop6h 55mFrontier
Deal found 12/6$184
This Priceline deal was found by Cheapflights users on 12/7. 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 12/196:12 amMDW - RDU
1 stop5h 08mFrontier
Mon 12/296:00 amRDU - MDW
1 stop8h 21mFrontier
Deal found 12/7$187
This Frontier deal was found by Cheapflights users on 12/7. 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 12/186:12 amMDW - IAD
1 stop11h 04mFrontier
Fri 1/26:05 amIAD - MDW
1 stop8h 16mFrontier
Deal found 12/7$188
This Delta deal was found by Cheapflights users on 12/7. 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.
Wed 12/246:08 pmMDW - RDU
1 stop4h 23mDelta
Thu 1/15:30 amRDU - MDW
1 stop4h 19mDelta
Deal found 12/7$197
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/186:12 amMDW - RDU
1 stop17h 01mFrontier
Tue 12/236:14 pmRDU - MDW
1 stop21h 23mFrontier
Deal found 12/8$200
This CheapOair deal was found by Cheapflights users on 12/7. 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 12/156:15 amMDW - IAD
1 stop10h 10mFrontier
Mon 12/299:58 pmIAD - MDW
1 stop25h 00mFrontier
Deal found 12/7$205
This CheapOair deal was found by Cheapflights users on 12/6. 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 12/256:12 amMDW - IAD
1 stop11h 04mFrontier
Mon 12/299:58 pmIAD - MDW
1 stop25h 00mFrontier
Deal found 12/6$209

Find flight deals from Midway to Virginia

Keep the following information in mind while searching for Midway to Virginia flight deals. Data was last updated December 8, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$123
(Kiwi.com)

One-way from

$56
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$380

Good round-trip deal

$288 or less
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Norfolk flights.
Search Deals
From Chicago Midway to Virginia
Search Deals
One-way flight from Chicago Midway to Virginia
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Virginia.
Search Deals

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 December 8, 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

Thu 1/8

12:41 pm-12:12 am

1 stop10h 31m

Raleigh-Durham

Sat 1/10

8:56 pm-10:59 pm

1 stop27h 03m

$163

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Wed 12/24

6:08 pm-11:31 pm

1 stop4h 23m

Raleigh-Durham

Thu 1/1

5:30 am-8:49 am

1 stop4h 19m

$197

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sun 2/1

6:20 am-4:33 pm

1 stop9h 13m

Washington, D.C. Dulles Intl

Mon 2/9

1:31 pm-7:58 pm

1 stop7h 27m

$197

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 12/25

6:12 am-6:16 pm

1 stop11h 04m

Washington, D.C. Dulles Intl

Mon 12/29

9:58 pm-9:58 pm

1 stop25h 00m

$209

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 2/5

6:20 am-4:28 pm

1 stop9h 08m

Washington, D.C. Dulles Intl

Mon 2/16

5:20 pm-11:25 pm

1 stop7h 05m

$215

ChicagoGreensboro

MDW - GSO

MDWGSO

Chicago Midway

Sat 1/10

5:31 pm-11:47 pm

1 stop5h 16m

Greensboro/H. Point

Sat 1/17

5:38 pm-10:07 pm

1 stop5h 29m

$219

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 1/2

6:12 am-1:39 pm

1 stop6h 27m

Norfolk

Fri 1/9

12:25 pm-10:21 pm

1 stop10h 56m

$222

ChicagoGreensboro

MDW - GSO

MDWGSO

Chicago Midway

Wed 2/11

6:00 am-11:51 am

1 stop4h 51m

Greensboro/H. Point

Mon 2/23

5:19 pm-10:42 pm

1 stop6h 23m

$224

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Tue 1/6

1:25 pm-4:15 pm

Nonstop1h 50m

Raleigh-Durham

Sun 1/18

6:00 am-7:15 am

Nonstop2h 15m

$229

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Thu 1/15

9:50 am-12:40 pm

Nonstop1h 50m

Raleigh-Durham

Sun 1/18

6:00 am-7:15 am

Nonstop2h 15m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

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, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Virginia (average of $155). Flying from Chicago Midway Airport to Virginia in December is currently the most expensive (average of $605). 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 December 8, 2025.

When flying from Chicago Midway Airport to Virginia, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 17% versus a flight in the afternoon.

What is the cheapest day to fly from Chicago Midway Airport to Virginia?

Use this chart to determine the cheapest time to fly round-trip from Midway to Virginia. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to Virginia flight should consider departing on Sunday mornings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago Midway Airport to Virginia

Explore weekly flight availability from Midway to Virginia. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 8, 2025.

The most flights from MDW to USVA are scheduled on a Friday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 December 8, 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
4,252 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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
4,252 reviews
Southwest
8.0
Very good
4,252 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

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 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, Delta, and Southwest can get you from Chicago Midway Airport to Virginia in just under 1h 50m. Your travel time can differ by up to 8h 41m. 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 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 $344 for a flight from Chicago Midway Airport to Virginia. The cheapest flight overall is $287 while the most popular route, (Chicago Midway - Washington, D.C. Dulles Intl) is currently priced at $128.

  • 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, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Virginia (average of $155). Flying from Chicago Midway Airport to Virginia in December is currently the most expensive (average of $605). 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 December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$230Average$368FlexibilityNo cancel feeOn-time63%

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