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$68+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RIC
Nov 24 — Dec 11
Mon 11/24
Mon 12/1
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 October 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$133
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$415

Good round-trip deal

$331 or less

Good one-way deal

$218 or less
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Norfolk flights.
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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 ($12 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 October 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 October 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/131:37 pmMDW - RDU
1 stop8h 21mFrontier
Sat 11/156:00 amRDU - MDW
1 stop13h 39mFrontier
Deal found 10/23$133
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/122:06 pmMDW - RDU
1 stop26h 56mFrontier
Wed 11/196:10 amRDU - MDW
1 stop7h 31mFrontier
Deal found 10/24$136
This CheapOair deal was found by Cheapflights users on 10/24. 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 11/66:30 amMDW - RDU
1 stop13h 41mFrontier
Tue 11/116:10 amRDU - MDW
1 stop6h 28mFrontier
Deal found 10/24$143
This Booking.com deal was found by Cheapflights users on 10/24. 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 11/96:30 amMDW - RDU
1 stop13h 41mFrontier
Thu 11/138:31 amRDU - MDW
1 stop7h 02mFrontier
Deal found 10/24$144
This Booking.com deal was found by Cheapflights users on 10/24. 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 12/112:16 pmMDW - IAD
1 stop23h 49mFrontier
Fri 12/125:19 pmIAD - MDW
1 stop5h 53mFrontier
Deal found 10/24$144
This Priceline deal was found by Cheapflights users on 10/23. 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.
Sat 11/811:36 amMDW - RDU
1 stop5h 41mFrontier
Mon 11/106:37 pmRDU - MDW
1 stop6h 53mFrontier
Deal found 10/23$150
This CheapOair deal was found by Cheapflights users on 10/22. 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 11/1312:30 pmMDW - DCA
1 stop8h 29mFrontier
Sat 11/158:15 amDCA - MDW
1 stop28h 15mFrontier
Deal found 10/22$150
This Priceline deal was found by Cheapflights users on 10/23. 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.
Sat 11/811:36 amMDW - IAD
1 stop7h 15mFrontier
Thu 11/135:34 pmIAD - MDW
1 stop5h 29mFrontier
Deal found 10/23$150
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/56:15 amMDW - IAD
1 stop9h 09mFrontier
Sun 12/712:04 pmIAD - MDW
1 stop11h 26mFrontier
Deal found 10/23$156
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 11/191:56 pmMDW - IAD
1 stop26h 50mFrontier
Wed 12/39:00 amIAD - MDW
2 stops29h 01mFrontier
Deal found 10/24$157
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 11/146:15 amMDW - IAD
1 stop9h 19mFrontier
Sat 11/155:58 amIAD - MDW
1 stop16h 37mFrontier
Deal found 10/23$160
This Trip.com deal was found by Cheapflights users on 10/23. 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 11/131:37 pmMDW - RDU
1 stop8h 21mFrontier
Mon 11/176:37 pmRDU - MDW
1 stop6h 53mFrontier
Deal found 10/23$162

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 October 25, 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

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 11/6

1:37 pm-12:11 am

1 stop9h 34m

Washington, D.C. Dulles Intl

Mon 11/10

5:44 pm-10:11 pm

1 stop5h 27m

$150

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Sat 11/8

11:36 am-7:51 pm

1 stop7h 15m

Washington, D.C. Dulles Intl

Mon 11/10

5:44 pm-10:11 pm

1 stop5h 27m

$150

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Wed 11/5

2:06 pm-8:20 pm

1 stop5h 14m

Washington, D.C. Dulles Intl

Sat 11/8

8:36 pm-9:12 am

1 stop13h 36m

$163

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 11/7

6:15 am-4:34 pm

1 stop9h 19m

Washington, D.C. Dulles Intl

Sat 11/8

8:36 pm-9:12 am

1 stop13h 36m

$164

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Fri 12/5

1:45 pm-4:30 pm

Nonstop1h 45m

Raleigh-Durham

Sun 12/7

5:45 am-6:50 am

Nonstop2h 05m

$170

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 12/5

3:52 pm-8:24 pm

1 stop27h 32m

Washington, D.C. Dulles Intl

Sun 12/7

12:04 pm-10:30 pm

1 stop11h 26m

$176

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Thu 11/6

6:25 am-4:34 pm

1 stop9h 09m

Washington, D.C. Dulles Intl

Sun 11/9

10:54 pm-12:30 am

1 stop26h 36m

$176

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 12/13

9:59 am-5:07 pm

1 stop6h 08m

Norfolk

Tue 12/16

5:15 am-9:41 am

1 stop5h 26m

$177

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Fri 12/5

5:13 pm-12:18 am

1 stop6h 05m

Raleigh-Durham

Sun 12/7

5:15 am-9:41 am

1 stop5h 26m

$177

ChicagoWashington, D.C.

MDW - DCA

MDWDCA

Chicago Midway

Mon 12/22

5:59 pm-11:57 pm

1 stop4h 58m

Washington, D.C. Reagan-National

Thu 12/25

12:32 pm-5:26 pm

1 stop5h 54m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Virginia (average of $154). Flying from Chicago Midway Airport to Virginia in April is currently the most expensive (average of $360). 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 October 25, 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 25% 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.

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 October 25, 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
4,237 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

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 1h 45m. Your travel time can differ by up to 7h 49m. 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 Southwest, which is currently one of the cheapest options available, starting at $75. Frontier flights start at $75 while deals on Delta start at $89 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 $331 for a flight from Chicago Midway Airport to Virginia. The cheapest flight overall is $286 while the most popular route, (Chicago Midway - Washington, D.C. Dulles Intl) is currently priced at $150.

  • 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Virginia (average of $154). Flying from Chicago Midway Airport to Virginia in April is currently the most expensive (average of $360). 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 October 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$230Average$363FlexibilityNo cancel feeOn-time63%

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