$55 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 2/2. 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$156
Richmond
Richmond1 stop$255
Charlottesville
Charlottesville1 stop$229
Roanoke
Roanoke1 stop$269
Raleigh
Raleigh1 stop$110
Washington, D.C.
Baltimorenonstop$98
Blountville
Blountville1 stop$299
Norfolk
Norfolk1 stop$156
Richmond
Richmond1 stop$255
Charlottesville
Charlottesville1 stop$229
Roanoke
Roanoke1 stop$269
Raleigh
Raleigh1 stop$110
Washington, D.C.
Baltimorenonstop$98
Blountville
Blountville1 stop$299

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, Dec 10 - Mon, Dec 15
Frontier Logo
2:49 pm - 12:12 amMDW-RDU
8h 23m1 stop
Frontier Logo
12:55 pm - 10:12 pmRDU-MDW
10h 17m1 stop
$110Frontier
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Mon, Nov 17 - Thu, Nov 20
Frontier Logo
9:15 am - 4:02 pmMDW-RDU
5h 47m1 stop
Frontier Logo
9:19 am - 4:30 pmRDU-MDW
8h 11m1 stop
$111Frontier
Find Deal
Wed, Jan 7 - Mon, Jan 12
Frontier Logo
3:52 pm - 2:55 pmMDW-RDU
22h 03m1 stop
Frontier Logo
12:53 pm - 11:25 pmRDU-MDW
11h 32m1 stop
$119Frontier
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Thu, Jan 8 - Sun, Jan 11
Frontier Logo
9:07 pm - 6:41 pmMDW-RDU
20h 34m1 stop
Frontier Logo
12:53 pm - 11:25 pmRDU-MDW
11h 32m1 stop
$124Frontier
Find Deal
Tue, Jan 20 - Thu, Jan 22
Southwest Logo
1:25 pm - 4:15 pmMDW-RDU
1h 50mnonstop
Southwest Logo
6:00 am - 7:15 amRDU-MDW
2h 15mnonstop
$158Southwest
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Tue, Dec 2 - Sun, Dec 7
Southwest Logo
6:05 pm - 8:55 pmMDW-RDU
1h 50mnonstop
Southwest Logo
5:45 am - 6:50 amRDU-MDW
2h 05mnonstop
$168Southwest
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Thu, Nov 20 - Sat, Nov 22
Multiple Airlines Logo
6:20 am - 1:35 pmMDW-RDU
6h 15m1 stop
Multiple Airlines Logo
8:39 pm - 11:42 amRDU-MDW
16h 03m1 stop
$175Multiple Airlines
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Mon, Dec 8 - Thu, Dec 11
Multiple Airlines Logo
6:15 am - 4:20 pmMDW-ORF
9h 05m1 stop
Multiple Airlines Logo
8:38 am - 9:58 pmORF-MDW
14h 20m1 stop
$176Multiple Airlines
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Wed, Dec 10 - Fri, Dec 12
Delta Logo
6:40 pm - 11:17 pmMDW-RDU
3h 37m1 stop
Delta Logo
5:29 am - 8:54 amRDU-MDW
4h 25m1 stop
$187Delta
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Wed, Dec 10 - Tue, Dec 16
Delta Logo
6:00 am - 11:45 amMDW-GSO
4h 45m1 stop
Delta Logo
7:00 am - 11:55 amGSO-MDW
5h 55m1 stop
$219Delta
Find Deal
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 Richmond, at $286 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 $356.

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 $385 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 Saturdays for the best deals.

Good to know

Low seasonJanuary
Cheapest flight$55
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Chicago Midway Airport to Richmond

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 in the evening, when round-trip flights cost $371 on average. Morning departures are around 1% more expensive 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 $416.

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. $169 one-way - $262 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 4241 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

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

Information on your arrival and departure airports