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Midway

$87+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
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 August 1, 2025.

Round-trip from

$173
(Southwest)

One-way from

$87
(Southwest)

Popular in

December

Cheapest in

September

Average price

$345

Good round-trip deal

$224 or less

Good one-way deal

$165 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 ($17 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 August 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 August 1, 2025.

This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/114:55 pmRDU - MDW
Nonstop1h 55mSouthwest
Sat 10/189:55 amMDW - RDU
Nonstop1h 50mSouthwest
Deal found 7/30$173
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/181:22 pmIAD - MDW
1 stop5h 55mAllegiant Air
Fri 8/229:32 amMDW - IAD
1 stop4h 51mAllegiant Air
Deal found 7/31$174
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/137:14 pmIAD - MDW
1 stop15h 04mFrontier
Sat 9/2010:51 amMDW - IAD
1 stop6h 33mFrontier
Deal found 7/30$177
This CheapOair deal was found by Cheapflights users on 7/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:00 pmRDU - MDW
1 stop14h 22mFrontier
Sat 9/610:51 amMDW - RDU
1 stop22h 02mFrontier
Deal found 7/31$178
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/97:30 amRIC - MDW
Nonstop1h 55mSouthwest
Wed 9/106:25 amMDW - RIC
1 stop4h 35mSouthwest
Deal found 7/30$191
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:45 amRDU - MDW
1 stop3h 50mDelta
Mon 9/86:17 pmMDW - RDU
1 stop3h 59mDelta
Deal found 7/31$197
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2310:04 amRIC - MDW
1 stop6h 24mDelta
Sat 9/66:00 amMDW - RIC
1 stop6h 27mDelta
Deal found 7/31$201
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3011:55 amDCA - MDW
Nonstop1h 55mSouthwest
Sat 9/610:05 amMDW - DCA
Nonstop1h 50mSouthwest
Deal found 7/31$217
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3010:18 amGSO - MDW
1 stop6h 10mDelta
Wed 9/31:08 pmMDW - GSO
1 stop3h 34mDelta
Deal found 7/30$219
This Delta deal was found by Cheapflights users on 7/29. 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.
Sat 8/305:25 pmIAD - MDW
1 stop4h 47mDelta
Tue 9/29:30 amMDW - IAD
1 stop12h 56mDelta
Deal found 7/29$227
This Mytrip deal was found by Cheapflights users on 8/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/167:00 amDCA - MDW
1 stop14h 54mFrontier
Sun 8/172:44 pmMDW - DCA
1 stop20h 20mFrontier
Deal found 8/1$228
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/115:30 pmCHO - MDW
1 stop5h 14mDelta
Tue 12/210:35 amMDW - CHO
1 stop5h 12mDelta
Deal found 7/31$229

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 August 1, 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

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/11

4:55 pm-5:50 pm

Nonstop1h 55m

Chicago Midway

Sat 10/18

9:55 am-12:45 pm

Nonstop1h 50m

$173

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 8/18

1:22 pm-6:17 pm

1 stop5h 55m

Chicago Midway

Fri 8/22

9:32 am-3:23 pm

1 stop4h 51m

$174

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/13

7:14 pm-9:18 am

1 stop15h 04m

Chicago Midway

Sat 9/20

10:51 am-6:24 pm

1 stop6h 33m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 8/30

10:57 am-8:22 am

1 stop22h 25m

Chicago Midway

Sat 9/6

10:51 am-9:53 am

1 stop22h 02m

$178

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 9/4

5:45 am-8:35 am

1 stop3h 50m

Chicago Midway

Mon 9/8

6:17 pm-11:16 pm

1 stop3h 59m

$197

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 9/4

4:25 pm-5:25 pm

Nonstop2h 00m

Chicago Midway

Tue 9/9

11:00 am-1:55 pm

Nonstop1h 55m

$199

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Sat 8/23

10:04 am-3:28 pm

1 stop6h 24m

Chicago Midway

Sat 9/6

6:00 am-1:27 pm

1 stop6h 27m

$201

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/30

11:55 am-12:50 pm

Nonstop1h 55m

Chicago Midway

Sat 9/6

10:05 am-12:55 pm

Nonstop1h 50m

$217

GreensboroChicago

GSO - MDW

GSOMDW

Greensboro/H. Point

Sat 8/30

5:15 pm-9:12 pm

1 stop4h 57m

Chicago Midway

Tue 9/2

6:17 pm-11:07 pm

1 stop3h 50m

$219

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 8/30

5:25 pm-9:12 pm

1 stop4h 47m

Chicago Midway

Tue 9/2

9:30 am-11:26 pm

1 stop12h 56m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 41 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 August 1, 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated August 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Allegiant Air from Virginia to Chicago Midway Airport to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,983 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Allegiant Air
7.2
Good
702 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,241 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $87. However, be on the lookout for offers from Frontier 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 $53. While the most popular route (Washington, D.C. Dulles Intl - Chicago Midway) can be booked for $174 on average our data indicates $327 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
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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.
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Portland to O'Hare Intl flights
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Philadelphia to Midway flights
Reagan-National to Midway flights
Oakland to O'Hare Intl flights
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Cleveland to O'Hare Intl flights
White Plains 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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$231Average$374FlexibilityNo cancel feeOn-time63%
DeltaCheapest$298Average$487FlexibilityNo cancel feeOn-timeN/A

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