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$72+ Cheap flights from Virginia to Midway (MDW)

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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Virginia to Midway

Keep the following information in mind while searching for Virginia to Midway flight deals. Data was last updated September 16, 2025.

Round-trip from

$138
(SmartFares)

One-way from

$72
(Priceline)

Popular in

January

Cheapest in

October

Average price

$361

Good round-trip deal

$288 or less

Good one-way deal

$139 or less
From Virginia to Chicago Midway
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One-way flight from Virginia to Chicago Midway
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Highest demand for flights based on searches. 4% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 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 Virginia to Chicago Midway.
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Price to beat on a one-way flight from Virginia to Chicago Midway.
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Find flight deals from Virginia to Midway

Cheapest flights from Virginia to Midway
Explore the most affordable flight options available from Virginia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/184:22 pmIAD - MDW
1 stop7h 25mFrontier
Mon 10/209:44 amMDW - IAD
1 stop4h 55mFrontier
Deal found 9/15$138
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:00 amRDU - MDW
Nonstop1h 55mSouthwest
Wed 10/2210:10 amMDW - RDU
Nonstop1h 50mSouthwest
Deal found 9/15$139
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.
Wed 10/159:00 amIAD - MDW
1 stop5h 38mFrontier
Tue 10/218:05 amMDW - IAD
1 stop10h 41mFrontier
Deal found 9/14$140
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/255:10 pmRDU - MDW
1 stop7h 10mFrontier
Mon 10/275:10 amMDW - RDU
1 stop11h 05mFrontier
Deal found 9/15$140
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:22 pmIAD - MDW
1 stop7h 25mFrontier
Mon 10/2712:03 pmMDW - IAD
1 stop10h 19mFrontier
Deal found 9/14$143
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:42 pmRDU - MDW
1 stop5h 38mFrontier
Thu 9/254:56 pmMDW - RDU
1 stop4h 54mFrontier
Deal found 9/14$143
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/251:55 pmIAD - MDW
1 stop10h 25mFrontier
Fri 9/266:20 amMDW - IAD
1 stop5h 35mFrontier
Deal found 9/14$144
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:42 pmRDU - MDW
1 stop5h 59mFrontier
Mon 10/68:19 amMDW - RDU
1 stop8h 49mFrontier
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.
Sat 9/277:14 pmIAD - MDW
1 stop15h 04mFrontier
Mon 9/296:21 amMDW - IAD
1 stop12h 48mFrontier
Deal found 9/14$145
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/246:45 amRDU - MDW
1 stop10h 13mFrontier
Mon 9/295:15 pmMDW - RDU
1 stop4h 43mFrontier
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.
Tue 9/236:45 amRDU - MDW
1 stop10h 13mFrontier
Mon 9/298:19 amMDW - RDU
1 stop8h 49mFrontier
Deal found 9/15$146
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 9/256:10 amIAD - MDW
1 stop10h 48mFrontier
Mon 9/295:15 pmMDW - IAD
1 stop6h 00mFrontier
Deal found 9/15$148

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia to Midway 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 Virginia to Chicago Midway Airport that are best for you.

Fly from

Virginia

Fly to

Midway

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 9/29

1:55 pm-11:20 pm

1 stop10h 25m

Chicago Midway

Mon 10/6

8:19 am-6:24 pm

1 stop9h 05m

$144

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 9/26

7:14 pm-9:51 am

1 stop15h 37m

Chicago Midway

Mon 9/29

6:21 am-8:09 pm

1 stop12h 48m

$144

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 9/29

6:42 pm-11:20 pm

1 stop5h 38m

Chicago Midway

Thu 10/2

4:56 pm-10:50 pm

1 stop4h 54m

$145

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/11

6:35 am-7:30 am

Nonstop1h 55m

Chicago Midway

Sat 10/18

5:45 pm-8:35 pm

Nonstop1h 50m

$149

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 11/1

4:55 pm-5:50 pm

Nonstop1h 55m

Chicago Midway

Mon 11/3

10:00 am-1:00 pm

Nonstop2h 00m

$158

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 11/1

8:36 pm-10:12 am

1 stop14h 36m

Chicago Midway

Mon 11/3

1:37 pm-12:11 am

1 stop9h 34m

$160

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 10/9

8:02 pm-4:20 pm

1 stop21h 18m

Chicago Midway

Mon 10/13

9:00 am-6:45 pm

1 stop8h 45m

$169

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/11

4:55 pm-5:50 pm

Nonstop1h 55m

Chicago Midway

Wed 10/15

6:05 pm-8:55 pm

Nonstop1h 50m

$174

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 11/18

1:40 pm-2:45 pm

Nonstop2h 05m

Chicago Midway

Mon 11/24

9:00 am-5:40 pm

1 stop7h 40m

$179

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 10/23

8:15 pm-11:15 pm

1 stop4h 00m

Chicago Midway

Sat 10/25

5:45 pm-8:35 pm

Nonstop1h 50m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 60 results
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Best time to book a flight from Virginia to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Virginia 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 Virginia to Chicago Midway Airport

What is the cheapest month to book a flight from Virginia to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Virginia to Chicago Midway Airport (average of $160). Flying from Virginia to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 VA to MDW?

Find hourly flight availability from Virginia to Midway. 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.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Virginia to Chicago Midway Airport as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Virginia to Midway. 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 Virginia to Chicago Midway Airport?

    Departing from Virginia to Chicago Midway Airport will take you 1h 55m. Virginia and Chicago Midway Airport are separated by a distance of 631 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Virginia to Chicago Midway Airport one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $78. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Virginia to Chicago Midway Airport for a low price.

  • What are the most popular routes from Virginia to Chicago Midway Airport?

    The most popular route from Virginia to Chicago Midway Airport is Washington, D.C. Dulles Intl - Chicago Midway. You may also consider Washington, D.C. Reagan-National - Chicago Midway or Raleigh-Durham - Chicago Midway.

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

    Looking at all options, your cheapest flight can be booked for $124. While the most popular route (Washington, D.C. Dulles Intl - Chicago Midway) can be booked for $140 on average, our data indicates $315 when flying from Virginia to Chicago Midway Airport.

  • Can I find deals for flights from Virginia to Midway that include hotel bookings?

    Yes. In addition to deals on Virginia to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Virginia to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Virginia to Midway.

  • Can I find deals for business class flights from Virginia to Midway?

    Yes. Cheapflights offers flight deals from Virginia to Midway 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 Virginia to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Virginia to Chicago Midway Airport (average of $160). Flying from Virginia to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Virginia to Midway

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to O'Hare Intl flights
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John F Kennedy Intl to Midway flights
Santa Ana to O'Hare Intl flights
Baltimore to Midway flights
LaGuardia to Midway flights
Atlanta to Midway flights
Newark to Midway flights
Los Angeles to Midway flights
Dulles Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
San Francisco to Midway flights
Raleigh to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Philadelphia to Midway flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Portland to O'Hare Intl flights
Burbank to O'Hare Intl flights
Hobby to O'Hare Intl flights
Providence to O'Hare Intl flights
Seattle to Midway flights
Reagan-National to Midway flights
Miami to O'Hare Intl flights
Hartford to O'Hare Intl flights
Denver to Midway flights
Cleveland to O'Hare Intl flights
Love Field to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Minneapolis to Midway flights
San Diego to O'Hare Intl flights
Boston to Midway flights
Orlando to O'Hare Intl flights

Top 2 airlines flying from Virginia to Midway

Discover the top 2 airlines that operate flights from Virginia to Midway. 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
DeltaCheapest$228Average$358FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$257Average$383FlexibilityNo cancel feeOn-time63%

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