$69 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 6/2. 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
Norfolk1 stop$309
Richmond
Richmondnonstop$314
Roanoke
Roanoke1 stop$289
Charlottesville
Charlottesville1 stop$289
Raleigh
Raleigh1 stop$178
Washington, D.C.
Baltimorenonstop$183
Blountville
Blountville1 stop$249
Norfolk
Norfolk1 stop$309
Richmond
Richmondnonstop$314
Roanoke
Roanoke1 stop$289
Charlottesville
Charlottesville1 stop$289
Raleigh
Raleigh1 stop$178
Washington, D.C.
Baltimorenonstop$183
Blountville
Blountville1 stop$249

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, May 28 - Thu, Jun 4
Frontier Logo
12:27 pm - 12:24 am
MDW
-
RDU
10h 57m
1 stop
Frontier Logo
12:54 pm - 10:02 pm
RDU
-
MDW
10h 08m
1 stop
$178Frontier
Thu, May 28 - Thu, Jun 4
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
$180Frontier
Sat, Aug 22 - Thu, Aug 27
Frontier Logo
11:59 am - 12:22 am
MDW
-
RDU
11h 23m
1 stop
Frontier Logo
12:54 pm - 10:11 pm
RDU
-
MDW
10h 17m
1 stop
$183Frontier
Sun, May 24 - Tue, May 26
Frontier Logo
6:00 am - 11:59 am
MDW
-
RDU
4h 59m
1 stop
Frontier Logo
6:15 am - 11:12 am
RDU
-
MDW
5h 57m
1 stop
$185Frontier
Fri, Jun 12 - Mon, Jun 15
Multiple Airlines Logo
9:23 pm - 8:04 pm
MDW
-
IAD
21h 41m
1 stop
Multiple Airlines Logo
11:17 am - 10:11 pm
IAD
-
MDW
11h 54m
1 stop
$221Multiple Airlines
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
3:00 pm - 9:55 pm
MDW
-
DCA
5h 55m
1 stop
Southwest Logo
11:40 am - 5:55 pm
DCA
-
MDW
7h 15m
2 stops
$222Southwest
Thu, May 21 - Wed, May 27
Multiple Airlines Logo
2:47 pm - 2:18 pm
MDW
-
IAD
22h 31m
1 stop
Multiple Airlines Logo
11:07 am - 10:02 pm
IAD
-
MDW
11h 55m
1 stop
$222Multiple Airlines
Wed, May 27 - Thu, May 28
Southwest Logo
1:30 pm - 4:15 pm
MDW
-
DCA
1h 45mnonstop
Southwest Logo
2:45 pm - 5:50 pm
DCA
-
MDW
4h 05m
1 stop
$224Southwest
Mon, Jun 1 - Wed, Jun 3
Delta Logo
6:36 pm - 10:56 pm
MDW
-
IAD
3h 20m
1 stop
Delta Logo
6:08 am - 10:00 am
IAD
-
MDW
4h 52m
1 stop
$228Delta
Wed, May 27 - Mon, Jun 1
Delta Logo
5:12 pm - 10:44 pm
MDW
-
DCA
4h 32m
1 stop
Delta Logo
6:00 am - 10:00 am
DCA
-
MDW
5h 00m
1 stop
$238Delta
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 morning, when round-trip flights cost $373 on average. Morning departures are around 11% 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 $417.

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$69
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 10% 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 - $270 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.
7.9
SouthwestOverall score based on 4303 reviews
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

10.0 ExcellentRobert, May 2026
LAS - SFO
Read more Southwest reviews

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

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

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

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.

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

Information on your arrival and departure airports