$99 Find Cheap Flights from Chicago Midway Airport to Virginia - Compare and Save

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 8/1. 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, 0 bags

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Cheap Flights from Midway to Virginia

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Norfolk
Norfolk1 stop$286
Richmond
Richmondnonstop$313
Roanoke
Roanoke1 stop$289
Charlottesville
Charlottesville1 stop$289
Raleigh
Raleigh1 stop$249
Washington, D.C.
Washington, D.C.1 stop$235
Blountville
Blountville1 stop$269
Norfolk
Norfolk1 stop$286
Richmond
Richmondnonstop$313
Roanoke
Roanoke1 stop$289
Charlottesville
Charlottesville1 stop$289
Raleigh
Raleigh1 stop$249
Washington, D.C.
Washington, D.C.1 stop$235
Blountville
Blountville1 stop$269

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

Wed, Jul 22 - Sat, Jul 25
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
Frontier Logo
6:49 am - 11:07 am
IAD
-
MDW
5h 18m
1 stop
$235Frontier
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
8:05 am - 3:00 pm
MDW
-
DCA
5h 55m
1 stop
Southwest Logo
1:00 pm - 5:50 pm
DCA
-
MDW
5h 50m
2 stops
$236Southwest
Wed, Jul 29 - Sat, Aug 1
Southwest Logo
8:55 pm - 11:50 pm
MDW
-
DCA
1h 55mnonstop
Southwest Logo
6:10 am - 7:10 am
DCA
-
MDW
2h 00mnonstop
$237Southwest
Sat, Aug 8 - Sat, Aug 15
Delta Logo
6:42 pm - 10:59 pm
MDW
-
DCA
3h 17m
1 stop
Delta Logo
6:30 pm - 10:36 pm
DCA
-
MDW
5h 06m
1 stop
$238Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
6:42 pm - 11:26 pm
MDW
-
IAD
3h 44m
1 stop
Delta Logo
6:00 am - 10:10 am
IAD
-
MDW
5h 10m
1 stop
$238Delta
Thu, Sep 17 - Mon, Sep 21
Frontier Logo
7:25 am - 5:36 pm
MDW
-
IAD
9h 11m
1 stop
Frontier Logo
7:00 am - 10:58 am
IAD
-
MDW
4h 58m
1 stop
$240Frontier
Sat, Aug 29 - Mon, Aug 31
Southwest Logo
7:50 am - 3:55 pm
MDW
-
DCA
7h 05m
2 stops
Southwest Logo
1:00 pm - 5:50 pm
DCA
-
MDW
5h 50m
2 stops
$241Southwest
Thu, Aug 20 - Mon, Aug 24
Frontier Logo
11:50 am - 10:52 pm
MDW
-
IAD
10h 02m
1 stop
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
$241Frontier
Thu, Aug 20 - Mon, Aug 24
Frontier Logo
11:50 am - 10:52 pm
MDW
-
IAD
10h 02m
1 stop
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
$242Frontier
Thu, Aug 20 - Mon, Aug 24
Delta Logo
1:25 pm - 6:45 pm
MDW
-
DCA
4h 20m
1 stop
Delta Logo
6:30 pm - 10:36 pm
DCA
-
MDW
5h 06m
1 stop
$243Delta
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 5 days was to Norfolk, at $317 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 5 days was $317.

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

The average price for all round-trip flights from Chicago Midway Airport to Virginia depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Virginia is generally in the afternoon, when round-trip flights cost $356 on average. Morning departures are around 5% cheaper than evening flights, on average. The most expensive time of day to fly to Virginia is generally at night, which is peak travel time and where the average cost of a ticket is $567.

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 $356 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Virginia, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Virginia is July, when tickets cost $127 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $569 and $317 respectively.

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 Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday 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 Sundays for the best deals.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$99
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 12% 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.

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. $168 one-way - $278 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.
7.9
SouthwestOverall score based on 4250 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent experience. WiFi worked on this leg of My trip

wifi wasn't working correctly so couldn't watch live tv

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)