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Midway

$55+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/412:53 pmRDU - MDW
1 stop6h 15mFrontier
Fri 12/123:52 pmMDW - RDU
1 stop23h 52mFrontier
Deal found 11/2$128
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Thu 12/43:21 pmRDU - MDW
1 stop7h 32mFrontier
Thu 12/117:23 pmMDW - RDU
1 stop13h 53mFrontier
Deal found 11/2$133
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:13 amRDU - MDW
1 stop9h 29mFrontier
Sun 12/76:15 amMDW - RDU
1 stop4h 53mFrontier
Deal found 11/2$138
This Southwest deal was found by Cheapflights users on 11/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/21:40 pmRDU - MDW
Nonstop2h 05mSouthwest
Tue 12/96:05 pmMDW - RDU
Nonstop1h 50mSouthwest
Deal found 11/2$139
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:19 pmIAD - MDW
1 stop5h 53mFrontier
Sun 12/76:15 amMDW - IAD
1 stop9h 09mFrontier
Deal found 11/2$141
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:13 amRDU - MDW
1 stop9h 29mFrontier
Sun 12/146:37 pmMDW - RDU
1 stop12h 46mFrontier
Deal found 11/2$142
This CheapOair deal was found by Cheapflights users on 11/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/108:14 pmRDU - MDW
1 stop26h 44mFrontier
Fri 12/123:52 pmMDW - RDU
1 stop23h 52mFrontier
Deal found 11/1$146
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:34 pmIAD - MDW
1 stop5h 29mFrontier
Mon 11/171:37 pmMDW - IAD
1 stop9h 34mFrontier
Deal found 11/2$150
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/128:00 amRDU - MDW
1 stop26h 12mFrontier
Mon 11/179:15 amMDW - RDU
1 stop5h 47mFrontier
Deal found 11/2$150
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:15 amDCA - MDW
1 stop28h 15mFrontier
Mon 11/1712:30 pmMDW - DCA
1 stop27h 29mFrontier
Deal found 11/2$150
This Booking.com deal was found by Cheapflights users on 11/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/88:36 pmIAD - MDW
1 stop13h 36mFrontier
Sat 11/151:37 pmMDW - IAD
1 stop9h 18mFrontier
Deal found 11/1$152
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Sat 12/65:45 amRDU - MDW
1 stop9h 14mFrontier
Sun 12/72:59 pmMDW - RDU
2 stops20h 01mFrontier
Deal found 11/2$156

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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$128
(CheapOair)

One-way from

$55
(Priceline)

Popular in

January

Cheapest in

September

Average price

$370

Good round-trip deal

$386 or less

Good one-way deal

$137 or less
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
Search Deals
From Virginia to Chicago Midway
Search Deals
One-way flight from Virginia to Chicago Midway
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Virginia to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Virginia to Chicago Midway.
Search Deals

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 November 3, 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 12/13

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Tue 12/16

6:05 pm-8:55 pm

Nonstop1h 50m

$139

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 12/5

5:19 pm-10:12 pm

1 stop5h 53m

Chicago Midway

Sun 12/7

6:15 am-4:24 pm

1 stop9h 09m

$142

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Mon 12/8

1:45 pm-4:30 pm

Nonstop1h 45m

$158

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/13

6:00 pm-11:47 pm

1 stop6h 47m

Chicago Midway

Tue 12/16

6:00 am-1:06 pm

1 stop6h 06m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 12/5

1:40 pm-2:45 pm

Nonstop2h 05m

Chicago Midway

Thu 12/11

10:00 am-1:00 pm

Nonstop2h 00m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 12/1

5:30 am-6:30 am

Nonstop2h 00m

Chicago Midway

Wed 12/3

10:00 am-1:00 pm

Nonstop2h 00m

$179

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 12/11

9:57 am-12:34 pm

1 stop3h 37m

Chicago Midway

Sat 12/13

1:14 pm-5:40 pm

1 stop3h 26m

$187

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 11/27

11:05 am-4:39 pm

1 stop6h 34m

Chicago Midway

Thu 12/4

5:13 pm-12:18 am

1 stop6h 05m

$187

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 12/5

5:29 am-8:54 am

1 stop4h 25m

Chicago Midway

Sat 12/6

6:00 am-11:34 am

1 stop4h 34m

$187

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 12/4

1:08 pm-6:00 pm

1 stop5h 52m

Chicago Midway

Sat 12/6

1:14 pm-5:40 pm

1 stop3h 26m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

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, September is the cheapest month in which you can book a flight from Virginia to Chicago Midway Airport (average of $175). Flying from Virginia to Chicago Midway Airport in December is currently the most expensive (average of $366). 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 November 3, 2025.

It’s optimal to fly from Virginia to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Virginia to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Virginia to Midway. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Virginia to Chicago Midway Airport flight should consider departing on Thursday afternoons when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Virginia to Chicago Midway Airport?

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 2h 05m. 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 $67. 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 $78. While the most popular route (Washington, D.C. Dulles Intl - Chicago Midway) can be booked for $110 on average, our data indicates $330 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, September is the cheapest month in which you can book a flight from Virginia to Chicago Midway Airport (average of $175). Flying from Virginia to Chicago Midway Airport in December is currently the most expensive (average of $366). 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
Porter
Benton Harbor

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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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Reagan-National to Midway flights
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Love Field to O'Hare Intl flights
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Los Angeles to Midway flights
Orlando to Midway flights
Boston to Midway flights
San Jose to O'Hare Intl flights
Hobby to O'Hare Intl flights
Salt Lake City to O'Hare Intl flights
Sacramento 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$228Average$228FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$229Average$380FlexibilityNo cancel feeOn-time63%

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