$47 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 8/7. 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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Best Virginia Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Norfolk
Norfolknonstop$113
Richmond
Richmondnonstop$105
Charlottesville
Charlottesville1 stop$229
Roanoke
Roanoke1 stop$229
Raleigh
Raleighnonstop$103
Blountville
Blountville1 stop$269
Norfolk
Norfolknonstop$113
Richmond
Richmondnonstop$105
Charlottesville
Charlottesville1 stop$229
Roanoke
Roanoke1 stop$229
Raleigh
Raleighnonstop$103
Blountville
Blountville1 stop$269

Cheap Flights from Midway to Virginia

 
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

Tue, Aug 5 - Tue, Aug 12
Southwest Logo
10:05 am - 12:55 pmMDW-DCA
1h 50mnonstop
Southwest Logo
6:35 pm - 7:30 pmDCA-MDW
1h 55mnonstop
$93Southwest
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Wed, Aug 6 - Mon, Aug 11
Southwest Logo
6:05 pm - 9:05 pmMDW-RDU
2h 00mnonstop
Southwest Logo
7:00 am - 7:55 amRDU-MDW
1h 55mnonstop
$103Southwest
Find Deal
Tue, Aug 5 - Tue, Aug 12
Southwest Logo
3:25 pm - 6:15 pmMDW-DCA
1h 50mnonstop
Southwest Logo
12:45 pm - 5:05 pmDCA-MDW
5h 20m1 stop
$103Southwest
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Thu, Aug 21 - Sat, Aug 23
Southwest Logo
10:55 am - 1:50 pmMDW-RIC
1h 55mnonstop
Southwest Logo
2:35 pm - 3:35 pmRIC-MDW
2h 00mnonstop
$105Southwest
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Sun, Aug 10 - Tue, Aug 12
Southwest Logo
5:25 am - 8:15 amMDW-DCA
1h 50mnonstop
Southwest Logo
11:55 am - 12:50 pmDCA-MDW
1h 55mnonstop
$106Southwest
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Wed, Sep 17 - Fri, Sep 19
Frontier Logo
9:00 am - 7:46 pmMDW-IAD
9h 46m1 stop
Frontier Logo
6:10 am - 3:58 pmIAD-MDW
10h 48m1 stop
$161Frontier
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Sat, Sep 27 - Sun, Sep 28
Frontier Logo
6:10 am - 11:55 pmMDW-IAD
16h 45m1 stop
Frontier Logo
1:41 pm - 11:20 pmIAD-MDW
10h 39m1 stop
$168Frontier
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Thu, Aug 21 - Mon, Aug 25
Delta Logo
6:04 am - 11:15 amMDW-RDU
4h 11m1 stop
Delta Logo
5:45 am - 8:35 amRDU-MDW
3h 50m1 stop
$197Delta
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Fri, Aug 8 - Mon, Aug 11
Delta Logo
6:47 pm - 12:39 amMDW-ORF
4h 52m1 stop
Delta Logo
5:59 pm - 9:44 pmORF-MDW
4h 45m1 stop
$197Delta
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Thu, Aug 14 - Mon, Aug 18
Allegiant Air Logo
10:53 am - 12:32 pmMDW-IAD
24h 39m2 stops
Allegiant Air Logo
1:22 pm - 6:17 pmIAD-MDW
5h 55m1 stop
$227Allegiant Air
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Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Virginia.

The cheapest ticket to Virginia from Chicago Midway Airport found in the last 72 hours was to Richmond, at $203 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 $230.

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.

No, with an average price for the route of $359, prices are generally cheapest when you fly direct.

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.


Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$47
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago Midway Airport to Reagan Washington National Airport

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 $361 on average. Morning departures are around 4% 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.

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 4247 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.6Entertainment
7.0Food
Airline reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

4.0 OkayGreg, Jul 2025PDX - DEN
Read more Southwest reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

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

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