$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 5/27. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$305
Richmond
Richmond1 stop$275
Roanoke
Roanoke1 stop$289
Charlottesville
Charlottesville1 stop$289
Raleigh
Raleigh1 stop$169
Washington, D.C.
Baltimorenonstop$177
Blountville
Blountville1 stop$339
Norfolk
Norfolknonstop$305
Richmond
Richmond1 stop$275
Roanoke
Roanoke1 stop$289
Charlottesville
Charlottesville1 stop$289
Raleigh
Raleigh1 stop$169
Washington, D.C.
Baltimorenonstop$177
Blountville
Blountville1 stop$339

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

mar., may. 26 - vie., may. 29
Frontier Logo
6:00 am - 11:59 am
MDW
-
RDU
4h 59m
1 stop
Frontier Logo
6:15 am - 11:09 am
RDU
-
MDW
5h 54m
1 stop
$169Frontier
jue., may. 21 - dom., may. 24
Frontier Logo
6:00 am - 11:59 am
MDW
-
RDU
4h 59m
1 stop
Frontier Logo
12:54 pm - 10:02 pm
RDU
-
MDW
10h 08m
1 stop
$171Frontier
jue., may. 28 - mar., jun. 2
Frontier Logo
6:00 am - 11:59 am
MDW
-
RDU
4h 59m
1 stop
Frontier Logo
3:24 pm - 10:02 pm
RDU
-
MDW
31h 38m
2 stops
$172Frontier
mié., may. 13 - mar., may. 26
Frontier Logo
12:04 pm - 7:24 am
MDW
-
RDU
18h 20m
2 stops
Frontier Logo
12:54 pm - 10:02 pm
RDU
-
MDW
10h 08m
1 stop
$173Frontier
jue., may. 21 - mié., jun. 24
Southwest Logo
8:20 am - 11:10 am
MDW
-
DCA
1h 50mnonstop
Southwest Logo
7:55 pm - 11:10 pm
DCA
-
MDW
4h 15m
1 stop
$218Southwest
mié., may. 27 - mié., jun. 3
Southwest Logo
1:55 pm - 6:40 pm
MDW
-
DCA
3h 45m
1 stop
Southwest Logo
8:00 am - 11:35 am
DCA
-
MDW
4h 35m
1 stop
$223Southwest
sáb., may. 23 - mar., may. 26
Delta Logo
5:10 pm - 11:44 pm
MDW
-
DCA
5h 34m
1 stop
Delta Logo
6:00 am - 10:00 am
DCA
-
MDW
5h 00m
1 stop
$228Delta
lun., jun. 1 - mié., jun. 3
Delta Logo
6:36 pm - 10:56 pm
MDW
-
IAD
3h 20m
1 stop
Delta Logo
11:58 am - 5:56 pm
IAD
-
MDW
6h 58m
1 stop
$228Delta
vie., may. 15 - dom., may. 17
Multiple Airlines Logo
4:52 pm - 10:55 am
MDW
-
ORF
17h 03m
2 stops
Multiple Airlines Logo
8:49 pm - 3:57 pm
ORF
-
MDW
20h 08m
1 stop
$306Multiple Airlines
jue., jun. 25 - dom., jun. 28
Multiple Airlines Logo
2:46 pm - 9:13 am
MDW
-
ORF
17h 27m
2 stops
Multiple Airlines Logo
12:21 pm - 11:09 am
ORF
-
MDW
23h 48m
1 stop
$307Multiple 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.

How much is a round-trip flight from Chicago Midway Airport to Virginia?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Virginia departing in May.

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 Norfolk, at $307 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Richmond (RIC), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $337.

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 $357 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 in the evening, which is peak travel time and where the average cost of a ticket is $392.

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 $350 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 May, when tickets cost $108 (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, 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 Sundays for the best deals.

Good to know

Low seasonJanuary
Cheapest flight$71
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 9% lower on average.
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. $144 one-way - $266 round-trip

Reviews of the top airlines 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 4315 reviews
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

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

Information on your arrival and departure airports