$69 Find Cheap Flights from Chicago 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 Chicago to Virginia departing on 8/11. 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 Chicago to Virginia

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Norfolk
Norfolk1 stop$307
Richmond
Richmondnonstop$312
Roanoke
Roanokenonstop$268
Charlottesville
Charlottesvillenonstop$269
Raleigh
Raleigh1 stop$184
Washington, D.C.
Baltimore1 stop$207
Blountville
Blountvillenonstop$229
Norfolk
Norfolk1 stop$307
Richmond
Richmondnonstop$312
Roanoke
Roanokenonstop$268
Charlottesville
Charlottesvillenonstop$269
Raleigh
Raleigh1 stop$184
Washington, D.C.
Baltimore1 stop$207
Blountville
Blountvillenonstop$229

Book Cheap Chicago 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 Chicago 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 Chicago to Virginia

Sat, Jun 6 - Mon, Jun 8
Frontier Logo
1:29 pm - 12:26 am
ORD
-
RDU
9h 57m
1 stop
Frontier Logo
12:33 pm - 8:03 am
RDU
-
ORD
20h 30m
1 stop
$184Frontier
Thu, Jul 23 - Tue, Jul 28
Frontier Logo
6:00 am - 12:25 am
MDW
-
RDU
17h 25m
1 stop
Frontier Logo
6:15 am - 11:07 am
RDU
-
MDW
5h 52m
1 stop
$185Frontier
Thu, Aug 13 - Sun, Aug 16
Multiple Airlines Logo
5:13 pm - 9:00 am
ORD
-
RDU
14h 47m
1 stop
Multiple Airlines Logo
12:59 pm - 7:53 am
RDU
-
ORD
19h 54m
1 stop
$190Multiple Airlines
Tue, Jun 9 - Mon, Jun 15
Multiple Airlines Logo
4:59 pm - 9:00 am
ORD
-
RDU
15h 01m
1 stop
Multiple Airlines Logo
12:10 pm - 8:03 am
RDU
-
ORD
20h 53m
1 stop
$194Multiple Airlines
Wed, Aug 26 - Wed, Sep 2
American Airlines Logo
9:30 am - 2:59 pm
ORD
-
DCA
4h 29m
1 stop
American Airlines Logo
1:59 pm - 3:25 pm
DCA
-
ORD
2h 26mnonstop
$228American Airlines
Wed, Sep 2 - Thu, Sep 3
Southwest Logo
8:50 am - 3:00 pm
MDW
-
DCA
5h 10m
1 stop
Southwest Logo
9:15 pm - 10:10 pm
DCA
-
MDW
1h 55mnonstop
$228Southwest
Tue, Jun 9 - Wed, Jun 24
American Airlines Logo
9:46 am - 2:20 pm
ORD
-
DCA
3h 34m
1 stop
American Airlines Logo
10:10 pm - 11:30 pm
DCA
-
ORD
2h 20mnonstop
$230American Airlines
Wed, Jun 10 - Wed, Jun 17
Southwest Logo
5:40 am - 8:25 am
MDW
-
DCA
1h 45mnonstop
Southwest Logo
7:25 am - 12:15 pm
DCA
-
MDW
5h 50m
1 stop
$230Southwest
Wed, Jun 10 - Wed, Jun 17
United Airlines Logo
9:55 pm - 12:59 am
ORD
-
IAD
2h 04mnonstop
United Airlines Logo
10:15 pm - 11:26 pm
IAD
-
ORD
2h 11mnonstop
$234United Airlines
Thu, Aug 6 - Mon, Aug 10
United Airlines Logo
7:00 am - 9:59 am
ORD
-
DCA
1h 59mnonstop
United Airlines Logo
1:00 pm - 2:18 pm
DCA
-
ORD
2h 18mnonstop
$239United Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Virginia flights

Get data-powered insights and trends into flights from Chicago 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 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 to Virginia departing in June.

What is the cheapest Chicago 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 found in the last 72 hours was to Staunton, at $233 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Norfolk (ORF), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $317.

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

The average price for all round-trip flights from Chicago 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 $381 on average. Morning departures are around 5% 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 $402.

Can I save money by flying with a layover from Chicago 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.

No, with an average price for the route of $413, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Virginia?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago 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 to Virginia is January, when tickets cost $74 (return) on average. On the other hand, the most expensive months are November and June, when the average cost of round-trip tickets is $157 and $140 respectively.

What’s the cheapest day of the week to fly from Chicago to Virginia?

The average price of all round-trip flights from Chicago to Virginia clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Virginia on a Wednesday and more expensive on a Monday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Sundays for better deals.

How far in advance should I book a flight from Chicago to Virginia?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Virginia, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Virginia, you should book around 4 weeks before departure, which saves you about 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$69
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 2% 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 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 to Virginia.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Virginia?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 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 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 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 to Virginia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Chicago 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 Chicago 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 4280 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

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.

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

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

Cabin class types available on flights to Virginia

Cabin classes available on flights to Virginia. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.