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$76+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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 1/295:01 pm
MDW
-
ORF
1 stop16h 47m
Frontier
Mon 2/211:43 am
ORF
-
MDW
1 stop11h 36m
Frontier
Deal found 1/21$151
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/55:01 pm
MDW
-
RDU
1 stop6h 10m
Frontier
Sun 2/86:10 am
RDU
-
MDW
1 stop6h 35m
Frontier
Deal found 1/21$154
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Wed 2/41:20 pm
MDW
-
ORF
1 stop20h 28m
Frontier
Fri 2/611:43 am
ORF
-
MDW
1 stop22h 00m
Frontier
Deal found 1/21$154
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 3/16:00 am
MDW
-
IAD
1 stop27h 40m
Frontier
Thu 3/55:37 pm
IAD
-
MDW
1 stop5h 52m
Frontier
Deal found 1/18$154
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Mon 2/26:20 am
MDW
-
RIC
1 stop11h 09m
Frontier
Fri 2/67:24 pm
RIC
-
MDW
1 stop14h 19m
Frontier
Deal found 1/21$154
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/126:25 am
MDW
-
IAD
1 stop9h 18m
Frontier
Mon 2/165:22 pm
IAD
-
MDW
1 stop26h 45m
Frontier
Deal found 1/21$157
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/16:20 am
MDW
-
ORF
1 stop27h 28m
Frontier
Thu 2/511:43 am
ORF
-
MDW
1 stop11h 36m
Frontier
Deal found 1/20$158
This Priceline deal was found by Cheapflights users on 1/19. 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.
Mon 2/25:01 pm
MDW
-
RDU
1 stop6h 10m
Frontier
Thu 2/56:10 am
RDU
-
MDW
1 stop6h 35m
Frontier
Deal found 1/19$160
This Expedia deal was found by Cheapflights users on 1/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:30 am
MDW
-
ORF
1 stop9h 58m
Frontier
Mon 2/2311:39 am
ORF
-
MDW
1 stop11h 50m
Frontier
Deal found 1/21$160
This Frontier deal was found by Cheapflights users on 1/21. 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 2/56:20 am
MDW
-
IAD
1 stop9h 08m
Frontier
Mon 2/95:33 pm
IAD
-
MDW
1 stop5h 46m
Frontier
Deal found 1/21$160
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/66:20 am
MDW
-
RDU
1 stop16h 51m
Frontier
Sun 2/86:10 am
RDU
-
MDW
1 stop6h 35m
Frontier
Deal found 1/20$161
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/207:45 am
MDW
-
RDU
1 stop6h 49m
Frontier
Thu 2/266:55 pm
RDU
-
MDW
1 stop24h 43m
Frontier
Deal found 1/19$162

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 January 21, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$154
(Kiwi.com)

One-way from

$76
(Trip.com)

Popular in

January

Cheapest in

December

Average price

$417

Good round-trip deal

$370 or less

Good one-way deal

$208 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
High demand for flights, 4% potential price rise
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 January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Virginia.
Search Deals
Price to beat on a one-way 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 January 21, 2026.
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

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sun 3/1

6:00 am-10:40 am

1 stop27h 40m

Washington, D.C. Dulles Intl

Thu 3/5

5:37 pm-10:29 pm

1 stop5h 52m

$154

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 2/28

8:00 am-9:25 am

1 stop24h 25m

Washington, D.C. Dulles Intl

Mon 3/2

8:15 am-8:27 pm

1 stop13h 12m

$160

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Mon 2/9

7:00 pm-12:05 pm

1 stop16h 05m

Norfolk

Thu 2/12

11:46 am-10:34 pm

1 stop11h 48m

$165

ChicagoRoanoke

MDW - ROA

MDWROA

Chicago Midway

Tue 2/17

6:40 pm-12:06 am

1 stop4h 26m

Roanoke

Tue 2/24

6:00 am-11:59 am

1 stop6h 59m

$179

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 2/6

6:20 am-4:33 pm

1 stop9h 13m

Washington, D.C. Dulles Intl

Sat 2/14

11:37 am-9:08 pm

1 stop10h 31m

$195

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 2/20

6:00 am-5:13 pm

1 stop10h 13m

Washington, D.C. Dulles Intl

Mon 2/23

5:22 pm-10:29 pm

1 stop6h 07m

$201

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

Washington, D.C. Dulles Intl

Fri 2/27

2:58 pm-2:55 pm

2 stops24h 57m

$202

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Sat 3/7

12:45 pm-3:35 pm

Nonstop1h 50m

Raleigh-Durham

Sat 3/7

7:05 pm-8:10 pm

Nonstop2h 05m

$214

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 3/18

11:00 am-6:15 pm

1 stop6h 15m

Washington, D.C. Reagan-National

Tue 3/24

11:40 am-4:25 pm

1 stop5h 45m

$217

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Tue 3/17

6:34 pm-10:59 pm

1 stop3h 25m

Washington, D.C. Dulles Intl

Tue 3/24

6:01 am-9:56 am

1 stop4h 55m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 $569). 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 January 21, 2026.

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 in the morning, which can drop the price by up to 24% 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 January 17, 2026.

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.

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 January 21, 2026.
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
4,266 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

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
4,266 reviews
Southwest
8.0
Very good
4,266 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

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 25h 50m. 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.

  • 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 $569). 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$213Average$373FlexibilityNo cancel feeOn-time63%

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