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$64+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
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 February 2, 2026.

This Expedia deal was found by Cheapflights users on 1/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/199:05 am
MDW
-
IAD
1 stop6h 38m
Frontier
Sat 2/2110:29 am
IAD
-
MDW
1 stop12h 04m
Frontier
Deal found 1/30$144
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/277:53 pm
MDW
-
IAD
1 stop12h 41m
Frontier
Mon 3/25:22 pm
IAD
-
MDW
1 stop26h 45m
Frontier
Deal found 1/31$147
This Frontier deal was found by Cheapflights users on 2/1. 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 2/266:25 am
MDW
-
IAD
1 stop9h 18m
Frontier
Mon 3/25:22 pm
IAD
-
MDW
1 stop6h 07m
Frontier
Deal found 2/1$148
This Frontier deal was found by Cheapflights users on 1/31. 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 2/199:05 am
MDW
-
IAD
1 stop6h 38m
Frontier
Mon 2/235:22 pm
IAD
-
MDW
1 stop6h 07m
Frontier
Deal found 1/31$154
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sat 3/76:00 am
MDW
-
IAD
1 stop17h 31m
Frontier
Sat 3/148:09 am
IAD
-
MDW
1 stop14h 36m
Frontier
Deal found 2/1$156
This Frontier deal was found by Cheapflights users on 2/1. 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 4/92:56 pm
MDW
-
RDU
1 stop8h 19m
Frontier
Tue 4/144:07 pm
RDU
-
MDW
1 stop7h 12m
Frontier
Deal found 2/1$160
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:05 am
MDW
-
IAD
1 stop17h 26m
Frontier
Wed 3/186:20 am
IAD
-
MDW
1 stop16h 59m
Frontier
Deal found 1/30$160
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/186:05 am
MDW
-
IAD
1 stop17h 16m
Frontier
Sat 3/215:05 am
IAD
-
MDW
1 stop18h 04m
Frontier
Deal found 2/2$161
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/57:30 am
MDW
-
IAD
1 stop8h 13m
Frontier
Mon 3/96:20 am
IAD
-
MDW
1 stop16h 59m
Frontier
Deal found 2/1$162
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/19:04 pm
MDW
-
IAD
1 stop12h 36m
Frontier
Thu 3/511:22 am
IAD
-
MDW
1 stop5h 54m
Frontier
Deal found 2/1$163
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/136:48 pm
MDW
-
RDU
1 stop28h 22m
Frontier
Tue 2/176:20 am
RDU
-
MDW
1 stop13h 47m
Frontier
Deal found 1/31$166
This Trip.com deal was found by Cheapflights users on 1/31. 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.
Tue 3/1011:19 am
MDW
-
RDU
1 stop9h 34m
Frontier
Wed 3/114:12 pm
RDU
-
MDW
1 stop7h 07m
Frontier
Deal found 1/31$168

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 February 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$144
(Expedia)

One-way from

$64
(Frontier)

Popular in

April

Cheapest in

December

Average price

$361

Good round-trip deal

$337 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. 5% potential increase in price ($22 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 February 2026
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 February 2, 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

Mon 3/2

6:00 am-4:08 pm

1 stop9h 08m

Washington, D.C. Dulles Intl

Thu 3/5

11:22 am-10:29 pm

1 stop12h 07m

$173

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 4/23

2:20 pm-12:36 am

1 stop9h 16m

Washington, D.C. Dulles Intl

Mon 4/27

9:51 am-7:31 pm

1 stop10h 40m

$181

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Tue 3/17

11:19 am-9:53 pm

1 stop9h 34m

Raleigh-Durham

Thu 3/19

4:07 pm-10:19 pm

1 stop7h 12m

$189

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Sat 5/2

7:30 am-5:04 pm

1 stop8h 34m

Raleigh-Durham

Sun 5/3

10:38 pm-8:04 am

1 stop10h 26m

$190

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Sat 2/14

5:55 pm-8:45 pm

Nonstop1h 50m

Washington, D.C. Reagan-National

Sat 2/21

6:15 am-7:25 am

Nonstop2h 10m

$195

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Wed 3/18

8:30 pm-11:15 pm

Nonstop1h 45m

Washington, D.C. Reagan-National

Tue 3/24

3:35 pm-4:50 pm

Nonstop2h 15m

$197

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 3/7

6:00 am-12:31 am

1 stop17h 31m

Washington, D.C. Dulles Intl

Thu 3/12

8:15 am-3:52 pm

1 stop8h 37m

$197

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 2/12

6:25 am-10:44 am

1 stop27h 19m

Washington, D.C. Dulles Intl

Mon 2/16

5:22 pm-7:07 pm

1 stop26h 45m

$197

ChicagoRichmond

MDW - RIC

MDWRIC

Chicago Midway

Mon 3/2

9:22 pm-9:54 pm

2 stops23h 32m

Richmond Byrd Intl

Mon 3/9

1:08 pm-8:53 pm

1 stop8h 45m

$200

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 2/20

6:48 pm-9:34 am

1 stop13h 46m

Washington, D.C. Dulles Intl

Sun 2/22

9:07 pm-1:08 pm

2 stops17h 01m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

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 February 2, 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 26% 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 31, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Virginia flight should consider departing on Wednesday at noon 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 February 2, 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
4,271 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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
4,271 reviews
Southwest
8.0
Very good
4,271 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

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, Southwest, and Delta can get you from Chicago Midway Airport to Virginia in just under 1h 50m. Your travel time can differ by up to 7h 18m. Chicago Midway Airport and Virginia are separated by a distance of 599 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 - Raleigh-Durham or Chicago Midway - Washington, D.C. Reagan-National as they are the most popular.

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

    On average you can expect to pay $443 for a flight from Chicago Midway Airport to Virginia. The cheapest flight overall is $389 while the most popular route, (Chicago Midway - Washington, D.C. Dulles Intl) is currently priced at $176.

  • 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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Midway to Tampa flights
Midway to Atlanta flights
O'Hare Intl to Charlotte 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 February 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$213Average$372FlexibilityNo cancel feeOn-time63%

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