$64 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 2/28. 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$133
Richmond
Richmond1 stop$133
Roanoke
Roanoke1 stop$179
Charlottesville
Charlottesville1 stop$197
Raleigh
Raleigh1 stop$168
Washington, D.C.
Baltimore1 stop$119
Blountville
Blountville1 stop$157
Norfolk
Norfolk1 stop$133
Richmond
Richmond1 stop$133
Roanoke
Roanoke1 stop$179
Charlottesville
Charlottesville1 stop$197
Raleigh
Raleigh1 stop$168
Washington, D.C.
Baltimore1 stop$119
Blountville
Blountville1 stop$157

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, Feb 18 - Mon, Feb 23
Frontier Logo
7:00 am - 10:51 am
MDW
-
ORF
26h 51m
1 stop
Frontier Logo
11:39 am - 10:29 pm
ORF
-
MDW
11h 50m
1 stop
$133Frontier
Wed, Feb 18 - Mon, Feb 23
Frontier Logo
7:00 am - 10:07 am
MDW
-
RIC
26h 07m
1 stop
Frontier Logo
10:35 am - 7:47 pm
RIC
-
MDW
10h 12m
1 stop
$133Frontier
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
6:25 am - 9:40 am
MDW
-
RIC
26h 15m
1 stop
Frontier Logo
10:35 am - 10:29 pm
RIC
-
MDW
12h 54m
1 stop
$142Frontier
Sat, Mar 7 - Wed, Mar 11
Frontier Logo
6:00 am - 12:31 am
MDW
-
IAD
17h 31m
1 stop
Frontier Logo
6:20 am - 10:19 pm
IAD
-
MDW
16h 59m
1 stop
$145Frontier
Wed, Mar 4 - Mon, Mar 9
Delta Logo
6:00 am - 12:17 pm
MDW
-
TRI
5h 17m
1 stop
Delta Logo
7:17 pm - 10:31 pm
TRI
-
MDW
4h 14m
1 stop
$157Delta
Thu, Feb 19 - Tue, Feb 24
Multiple Airlines Logo
12:22 pm - 11:17 am
MDW
-
RIC
21h 55m
1 stop
Multiple Airlines Logo
8:00 am - 7:07 pm
RIC
-
MDW
12h 07m
2 stops
$158Multiple Airlines
Tue, Apr 21 - Mon, Apr 27
Delta Logo
6:00 am - 1:03 pm
MDW
-
TRI
6h 03m
1 stop
Delta Logo
7:15 pm - 10:28 pm
TRI
-
MDW
4h 13m
1 stop
$159Delta
Wed, Feb 18 - Mon, Feb 23
Multiple Airlines Logo
7:00 am - 10:07 am
MDW
-
RIC
26h 07m
1 stop
Multiple Airlines Logo
1:08 pm - 7:07 pm
RIC
-
MDW
30h 59m
2 stops
$161Multiple Airlines
Sat, Mar 28 - Wed, Apr 1
Southwest Logo
6:05 pm - 8:55 pm
MDW
-
DCA
1h 50mnonstop
Southwest Logo
9:05 am - 10:15 am
DCA
-
MDW
2h 10mnonstop
$200Southwest
Sat, Mar 7 - Sat, Mar 14
Southwest Logo
6:30 am - 9:25 am
MDW
-
DCA
1h 55mnonstop
Southwest Logo
3:45 pm - 4:55 pm
DCA
-
MDW
2h 10mnonstop
$202Southwest
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 72 hours was to Norfolk, at $293 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 $293.

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 $331 on average.

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, Saturday 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$64
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 8% 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.

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

    The cheapest time of day to fly to Virginia is generally at night, when round-trip flights cost $370 on average. Morning departures are around 4% cheaper 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 $397.

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 - $281 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.
8.0
SouthwestOverall score based on 4280 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

10.0 ExcellentCarol, Feb 2026
DEN - MSP
Read more Southwest reviews

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

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

Information on your arrival and departure airports