$105 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 9/15. 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

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
Norfolknonstop$329
Richmond
Richmond1 stop$323
Roanoke
Roanoke1 stop$289
Charlottesville
Charlottesville1 stop$289
Washington, D.C.
Baltimore1 stop$239
Raleigh
Raleigh1 stop$240
Blountville
Blountville1 stop$269
Norfolk
Norfolknonstop$329
Richmond
Richmond1 stop$323
Roanoke
Roanoke1 stop$289
Charlottesville
Charlottesville1 stop$289
Washington, D.C.
Baltimore1 stop$239
Raleigh
Raleigh1 stop$240
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

Sat, Jul 18 - Tue, Jul 21
Frontier Logo
12:11 pm - 12:03 am
MDW
-
RDU
10h 52m
1 stop
Frontier Logo
6:15 am - 11:07 am
RDU
-
MDW
5h 52m
1 stop
$240Frontier
Wed, Jul 15 - Sat, Jul 18
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
$240Frontier
Sat, Sep 26 - Mon, Sep 28
Southwest Logo
7:55 am - 4:55 pm
MDW
-
DCA
8h 00m
2 stops
Southwest Logo
1:00 pm - 5:50 pm
DCA
-
MDW
5h 50m
2 stops
$241Southwest
Thu, Aug 27 - Mon, Aug 31
Frontier Logo
11:50 am - 11:59 pm
MDW
-
RDU
11h 09m
1 stop
Frontier Logo
1:21 pm - 8:31 pm
RDU
-
MDW
8h 10m
1 stop
$241Frontier
Tue, Jul 21 - Fri, Jul 24
Southwest Logo
5:05 pm - 7:55 pm
MDW
-
DCA
1h 50mnonstop
Southwest Logo
7:05 pm - 8:15 pm
DCA
-
MDW
2h 10mnonstop
$243Southwest
Sun, Sep 20 - Sat, Sep 26
Frontier Logo
7:25 am - 7:30 am
MDW
-
RDU
23h 05m
1 stop
Frontier Logo
4:20 pm - 9:58 pm
RDU
-
MDW
6h 38m
1 stop
$244Frontier
Wed, Sep 23 - Sun, Oct 4
Frontier Logo
7:25 am - 3:07 pm
MDW
-
RDU
6h 42m
1 stop
Frontier Logo
6:35 am - 10:58 am
RDU
-
MDW
5h 23m
1 stop
$245Frontier
Tue, Jul 21 - Tue, Jul 21
Delta Logo
6:00 am - 11:27 am
MDW
-
DCA
4h 27m
1 stop
Delta Logo
6:30 pm - 10:15 pm
DCA
-
MDW
4h 45m
1 stop
$253Delta
Thu, Sep 3 - Tue, Sep 8
Delta Logo
9:24 am - 4:38 pm
MDW
-
IAD
6h 14m
1 stop
Delta Logo
11:10 am - 4:57 pm
IAD
-
MDW
6h 47m
1 stop
$257Delta
Tue, Aug 25 - Sun, Aug 30
Multiple Airlines Logo
6:05 am - 12:25 pm
MDW
-
ORF
5h 20m
1 stop
Multiple Airlines Logo
12:59 pm - 10:55 am
ORF
-
MDW
22h 56m
2 stops
$333Multiple Airlines
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 $262 on average. Morning departures are around 6% 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 $489.

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 $359 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$105
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 11% 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.

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. $159 one-way - $297 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 4242 reviews
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)