$54 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 11/6. 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

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 Chicago to Virginia

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Norfolk
Norfolk1 stop$214
Richmond
Richmond1 stop$238
Charlottesville
Charlottesvillenonstop$209
Roanoke
Roanokenonstop$209
Raleigh
Raleighnonstop$104
Washington, D.C.
Baltimorenonstop$88
Blountville
Blountville1 stop$269
Norfolk
Norfolk1 stop$214
Richmond
Richmond1 stop$238
Charlottesville
Charlottesvillenonstop$209
Roanoke
Roanokenonstop$209
Raleigh
Raleighnonstop$104
Washington, D.C.
Baltimorenonstop$88
Blountville
Blountville1 stop$269

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

Thu, Nov 6 - Tue, Nov 11
Frontier Logo
1:37 pm - 10:58 pmMDW-RDU
8h 21m1 stop
Frontier Logo
6:10 am - 11:38 amRDU-MDW
6h 28m1 stop
$104Frontier
Find Deal
Fri, Oct 31 - Mon, Nov 3
Frontier Logo
1:55 pm - 5:01 pmORD-RDU
2h 06mnonstop
Frontier Logo
7:05 pm - 12:11 amRDU-ORD
6h 06m1 stop
$104Frontier
Find Deal
Wed, Nov 12 - Wed, Nov 19
United Airlines Logo
6:40 pm - 9:49 pmORD-RDU
2h 09mnonstop
United Airlines Logo
4:49 pm - 6:18 pmRDU-ORD
2h 29mnonstop
$139United Airlines
Find Deal
Wed, Nov 12 - Wed, Nov 19
American Airlines Logo
9:21 am - 12:31 pmORD-RDU
2h 10mnonstop
American Airlines Logo
1:11 pm - 2:37 pmRDU-ORD
2h 26mnonstop
$149American Airlines
Find Deal
Sun, Nov 16 - Wed, Nov 19
United Airlines Logo
7:10 am - 10:14 amORD-RDU
2h 04mnonstop
United Airlines Logo
10:00 am - 11:25 amRDU-ORD
2h 25mnonstop
$158United Airlines
Find Deal
Sat, Nov 8 - Thu, Nov 13
Southwest Logo
9:50 am - 12:45 pmMDW-RDU
1h 55mnonstop
Southwest Logo
12:40 pm - 1:40 pmRDU-MDW
2h 00mnonstop
$168Southwest
Find Deal
Wed, Nov 5 - Sat, Nov 8
Southwest Logo
10:00 am - 1:00 pmMDW-RDU
2h 00mnonstop
Southwest Logo
5:10 pm - 6:15 pmRDU-MDW
2h 05mnonstop
$184Southwest
Find Deal
Wed, Oct 29 - Wed, Oct 29
American Airlines Logo
6:00 am - 10:59 amORD-DCA
3h 59m1 stop
American Airlines Logo
12:31 pm - 1:43 pmDCA-ORD
2h 12mnonstop
$192American Airlines
Find Deal
Thu, Nov 6 - Tue, Nov 11
Spirit Airlines Logo
10:52 am - 6:58 pmORD-ORF
7h 06m1 stop
Spirit Airlines Logo
6:33 pm - 2:31 pmORF-ORD
20h 58m2 stops
$218Spirit Airlines
Find Deal
Tue, Nov 11 - Wed, Nov 12
Spirit Airlines Logo
1:48 pm - 5:38 pmORD-ORF
26h 50m3 stops
Spirit Airlines Logo
7:53 pm - 11:12 amORF-ORD
16h 19m1 stop
$221Spirit Airlines
Find Deal
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.

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 Richmond, at $187 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Richmond (RIC), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $187.

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 $390, 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 September, when tickets cost $309 (return) on average. On the other hand, the most expensive months are June and October, when the average cost of round-trip tickets is $416 and $409 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 Sunday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Mondays 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 3 weeks before departure, which saves you about 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$54
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Chicago O'Hare 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.

  • 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 $351 on average. Morning departures are around 4% more expensive than evening flights, on average. The most expensive time of day to fly to Virginia is generally in the morning, which is peak travel time and where the average cost of a ticket is $396.

Reviews of the top 5 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.
8.0
SouthwestOverall score based on 4240 reviews
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

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.

2.0 MediocrePrincess, Oct 2025MSY - DAL
Read more Southwest reviews

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.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Vegas is such a quick flight that amenities aren’t the important part, in my opinion. Just get me there efficiently and safely, and that’s exactly what they did!

The flight was severely delayed due to the missing flight attendants.

Absolutely horrible. Usually pay $40-$50 to check luggage in. I tried to check my suitcase in and the price is raised to $70. That's ridiculously greedy c'mon. I had to leave my suitcase with all my clothes and hygiene products and repurchase once i landed in Atlanta. You guys make it really stressful to travel. Don't even want to travel anymore.

They cancelled the flight 3 hours prior departure. Had to spend $400 for a ne way flight with Delta Airlines! Spirit Airlines are not serios!

My luggage didn’t arrive at LAX, so that wasn’t a good experience.

Terrible seat, no in flight entertainment. No complimentary food or drinks. Seats really hurt my back after flying spirit for the day.

No Tumberlence smooth flight. Try to change the menu on Snacks.

I didn’t mind being delayed due to weather, but continuing to post (and not update) that we would be delayed until after the flight was already supposed to have taken off was a bit much. In the future, please announce the delay even if the time is still unknown.

Everything was fine, but there was no food or entertainment, so I didn’t know how to rate that.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

I think Frontier was very good at communication. Their app worked very well. Loading was great and the flight was nice and easy.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

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.

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