$71 Find Cheap Flights from Chicago Midway Airport to Virginia

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Virginia departing on 10/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Virginia

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Virginia, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Virginia, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Virginia

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Norfolk
Norfolk1 stop$199
Richmond
Richmond1 stop$214
Charlottesville
Charlottesville1 stop$239
Roanoke
Roanoke1 stop$229
Washington, D.C.
Baltimorenonstop$92
Raleigh
Raleigh1 stop$143
Blountville
Blountville1 stop$328
Norfolk
Norfolk1 stop$199
Richmond
Richmond1 stop$214
Charlottesville
Charlottesville1 stop$239
Roanoke
Roanoke1 stop$229
Washington, D.C.
Baltimorenonstop$92
Raleigh
Raleigh1 stop$143
Blountville
Blountville1 stop$328

Book Cheap Midway to Virginia Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Virginia that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Virginia

Thu, Oct 16 - Sun, Oct 19
Frontier Logo
11:49 am - 6:08 pmMDW-RDU
5h 19m1 stop
Frontier Logo
7:15 pm - 11:46 pmRDU-MDW
5h 31m1 stop
$143Frontier
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Fri, Oct 3 - Tue, Oct 7
Frontier Logo
5:15 pm - 11:39 pmMDW-IAD
5h 24m1 stop
Frontier Logo
9:00 am - 1:38 pmIAD-MDW
5h 38m1 stop
$143Frontier
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Fri, Oct 3 - Sun, Oct 5
Frontier Logo
6:21 am - 5:11 pmMDW-RDU
9h 50m1 stop
Frontier Logo
9:02 pm - 7:23 amRDU-MDW
11h 21m1 stop
$144Frontier
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Sat, Oct 18 - Mon, Oct 20
Frontier Logo
11:31 am - 8:53 pmMDW-IAD
8h 22m1 stop
Frontier Logo
4:45 pm - 11:46 pmIAD-MDW
8h 01m1 stop
$144Frontier
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Fri, Oct 24 - Sat, Oct 25
Southwest Logo
7:00 pm - 9:50 pmMDW-RDU
1h 50mnonstop
Southwest Logo
4:55 pm - 5:50 pmRDU-MDW
1h 55mnonstop
$158Southwest
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Thu, Nov 13 - Mon, Nov 17
Southwest Logo
7:30 pm - 10:20 pmMDW-RDU
1h 50mnonstop
Southwest Logo
5:30 am - 6:30 amRDU-MDW
2h 00mnonstop
$177Southwest
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Sat, Oct 25 - Sat, Oct 25
Delta Logo
6:00 am - 12:56 pmMDW-RDU
5h 56m1 stop
Delta Logo
6:40 pm - 10:14 pmRDU-MDW
4h 34m1 stop
$197Delta
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Thu, Oct 16 - Thu, Oct 23
Multiple Airlines Logo
11:49 am - 4:39 pmMDW-ORF
27h 50m1 stop
Multiple Airlines Logo
5:38 pm - 4:20 pmORF-MDW
23h 42m1 stop
$203Multiple Airlines
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Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
2:15 pm - 9:50 pmMDW-RIC
6h 35m1 stop
Multiple Airlines Logo
6:22 pm - 1:10 pmRIC-MDW
19h 48m1 stop
$214Multiple Airlines
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Mon, Oct 6 - Wed, Oct 8
Delta Logo
6:23 pm - 10:58 pmMDW-RDU
3h 35m1 stop
Delta Logo
5:44 am - 8:40 amRDU-MDW
3h 56m1 stop
$217Delta
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Booking Insights

KAYAK's insights & trends for Midway to Virginia flights

Get data-powered insights and trends into flights from Midway to Virginia to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Virginia flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Virginia from Chicago Midway Airport found in the last 72 hours was to Richmond, at $232 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Norfolk (ORF), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $251.

Can I save money by flying with a layover from Chicago Midway Airport to Virginia?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $319 on average.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Virginia?

The average price of all round-trip flights from Chicago Midway Airport to Virginia clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Virginia on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday is the most expensive day to fly from Chicago Midway Airport to Virginia. For your return ticket, we recommend flying on a Tuesday and avoiding Saturdays for the best deals.

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Good to know

Low seasonJanuary
Cheapest flight$71
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago Midway Airport to Norfolk

FAQs - booking Virginia flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Virginia?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Virginia.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Virginia?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Virginia is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Virginia?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to Virginia with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Virginia?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to Virginia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Virginia?

    The cheapest time of day to fly to Virginia is generally in the evening, when round-trip flights cost $371 on average. Morning departures are around 1% more expensive than evening flights, on average. The most expensive time of day to fly to Virginia is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $418.

Top tips for finding cheap flights to Virginia

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Washington, D.C. $112 one-way - $240 round-trip

Reviews of the top airline flying from Midway to Virginia

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Virginia. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Virginia? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4242 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Everything you need to know for your flight from Midway to Virginia

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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