$33 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 10/30. 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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Flights Deals

Best Virginia Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Norfolk
Norfolknonstop$113
Richmond
Richmondnonstop$105
Charlottesville
Charlottesvillenonstop$219
Roanoke
Roanokenonstop$194
Raleigh
Raleighnonstop$85
Washington, D.C.
Baltimorenonstop$82
Blountville
Blountville1 stop$266
Norfolk
Norfolknonstop$113
Richmond
Richmondnonstop$105
Charlottesville
Charlottesvillenonstop$219
Roanoke
Roanokenonstop$194
Raleigh
Raleighnonstop$85
Washington, D.C.
Baltimorenonstop$82
Blountville
Blountville1 stop$266

Cheap Flights from Chicago to Virginia

 
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

Sun, Sep 7 - Thu, Sep 11
Frontier Logo
11:32 am - 2:42 pmORD-RDU
2h 10mnonstop
Frontier Logo
3:36 pm - 5:02 pmRDU-ORD
2h 26mnonstop
$85Frontier
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Thu, Aug 7 - Thu, Aug 14
Frontier Logo
11:15 am - 2:28 pmORD-RDU
2h 13mnonstop
Frontier Logo
3:13 pm - 4:38 pmRDU-ORD
2h 25mnonstop
$92Frontier
Find Deal
Mon, Aug 18 - Thu, Aug 21
United Airlines Logo
6:00 am - 8:57 amORD-DCA
1h 57mnonstop
United Airlines Logo
1:00 pm - 2:13 pmDCA-ORD
2h 13mnonstop
$93United Airlines
Find Deal
Wed, Sep 10 - Sat, Sep 13
United Airlines Logo
11:40 am - 2:37 pmORD-IAD
1h 57mnonstop
United Airlines Logo
5:10 pm - 6:25 pmIAD-ORD
2h 15mnonstop
$93United Airlines
Find Deal
Thu, Aug 7 - Mon, Aug 11
Southwest Logo
5:30 am - 8:20 amMDW-DCA
1h 50mnonstop
Southwest Logo
9:00 pm - 10:00 pmDCA-MDW
2h 00mnonstop
$93Southwest
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Sat, Aug 9 - Mon, Aug 11
American Airlines Logo
1:20 pm - 4:16 pmORD-DCA
1h 56mnonstop
American Airlines Logo
3:50 pm - 5:11 pmDCA-ORD
2h 21mnonstop
$94American Airlines
Find Deal
Sat, Aug 16 - Wed, Aug 20
Southwest Logo
10:05 am - 12:55 pmMDW-DCA
1h 50mnonstop
Southwest Logo
12:00 pm - 5:45 pmDCA-MDW
6h 45m1 stop
$103Southwest
Find Deal
Thu, Sep 4 - Sat, Sep 6
American Airlines Logo
4:55 pm - 8:06 pmORD-RIC
2h 11mnonstop
American Airlines Logo
4:11 pm - 5:39 pmRIC-ORD
2h 28mnonstop
$105American Airlines
Find Deal
Sat, Aug 16 - Mon, Aug 18
Spirit Airlines Logo
6:56 am - 2:13 pmORD-RIC
6h 17m1 stop
Spirit Airlines Logo
2:00 pm - 10:22 pmRIC-ORD
9h 22m1 stop
$171Spirit Airlines
Find Deal
Thu, Aug 21 - Thu, Aug 28
Spirit Airlines Logo
5:05 am - 6:45 pmORD-RIC
12h 40m1 stop
Spirit Airlines Logo
2:00 pm - 10:22 pmRIC-ORD
9h 22m1 stop
$176Spirit Airlines
Find Deal
Useful Info

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?

What is the cheapest Chicago to Virginia flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Virginia.

The cheapest ticket to Virginia from Chicago found in the last 72 hours was to Richmond, at $167 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 $217.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $421 on average.

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 $314 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $423 and $396 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 Tuesday and more expensive on a Sunday. On your return trip to Chicago, you should consider flying back on a Friday, 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. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.


Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$33
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Chicago O'Hare Airport to Raleigh

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 $340 on average. Morning departures are around 2% 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 $394.

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 4250 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.6Entertainment
Airline reviews

It was one and half hour late... Not sure if any other experience matters.

4.0 OkaySudhir, Jul 2025LGA - MCI
Read more Southwest reviews

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

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

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

The flight was delayed four and half hours for paperwork on a maintenance issue. Very frustrating.

It was okay delay was long but I made it

Flight was cancelled. No reason given. No apologies. Next available flight is two days later. Ruined our 4th of July plans.

The air fares are good, Charging me for every single thing 😩

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

Flight delayed over 3 or 4 hours because no captain to fly plane. I couldn’t make a connection and had to wait 9 hours for another flight. Had to fly red eye flight. Sucks

it was a quick trip. seats aren't that comfortable but because it was a quick trip it was ok. You need to have an N/A in your rating as I didn't have any food or entertainment so the only thing I could do was score low.

We paid for upgrade seats (3A & 3B) the seats on front and the seats behind us got complimentary water & soda, but we got charged, had to pay for everything. Does not make any sense ?

Unfortunately, spirits crew had us boarding and parking the plane often, would wait long periods of time before allowing the people attending the flight on the plane to know what was going on this caused for my plane to not only get diverted but then canceled at an airport 2 hours away and basically stranded with charter buses MAYBE being hired. I was left with no choice but to stay overnight and use a comp room in Altantic City to then arrive home the next day. This trip was the first time seeing my partner since he joined the Air Force and this stressful ride caused unwarranted tears on what was supposed to be an east flight home. I understand weather is unpredictable but to have passengers deboard to then reboard an hour later to taxi on the runway for another hour to then basically leave an entire fight stranded. I waited almost 30 minutes at the airport and not one employee could tell me about a charter bus so I had to leave and make accommodations to stay overnight and get a ride home.

I wanted to upgrade my seat because I’m 6’2 and never have enough leg room for my comfort. They upgraded my seat for free putting me in an emergency exit seat. I was very comfortable

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

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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