$99 Find Cheap Flights from Chicago to Virginia - Compare and Save

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 7/28. 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.
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Cheap Flights from Chicago to Virginia

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Norfolk
Norfolk1 stop$280
Richmond
Richmond1 stop$315
Roanoke
Roanokenonstop$269
Charlottesville
Charlottesvillenonstop$269
Raleigh
Raleigh1 stop$249
Blountville
Blountvillenonstop$249
Norfolk
Norfolk1 stop$280
Richmond
Richmond1 stop$315
Roanoke
Roanokenonstop$269
Charlottesville
Charlottesvillenonstop$269
Raleigh
Raleigh1 stop$249
Blountville
Blountvillenonstop$249

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

Mon, Aug 24 - Wed, Sep 2
Frontier Logo
9:20 am - 6:29 pm
ORD
-
IAD
8h 09m
1 stop
Frontier Logo
8:39 pm - 7:53 am
IAD
-
ORD
12h 14m
1 stop
$234Frontier
Tue, Aug 11 - Thu, Aug 13
Multiple Airlines Logo
11:01 am - 6:01 pm
ORD
-
DCA
6h 00m
1 stop
Multiple Airlines Logo
1:59 pm - 8:52 pm
DCA
-
ORD
7h 53m
1 stop
$235Multiple Airlines
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
7:45 am - 3:15 pm
MDW
-
DCA
6h 30m
1 stop
Southwest Logo
1:00 pm - 5:50 pm
DCA
-
MDW
5h 50m
2 stops
$236Southwest
Sat, Sep 5 - Mon, Sep 7
United Airlines Logo
10:50 am - 1:55 pm
ORD
-
IAD
2h 05mnonstop
United Airlines Logo
10:35 am - 11:53 am
IAD
-
ORD
2h 18mnonstop
$237United Airlines
Sat, Aug 1 - Mon, Aug 3
American Airlines Logo
2:55 pm - 5:59 pm
ORD
-
DCA
2h 04mnonstop
American Airlines Logo
8:23 am - 10:00 am
DCA
-
ORD
2h 37mnonstop
$237American Airlines
Wed, Jul 29 - Sat, Aug 1
Southwest Logo
8:55 pm - 11:50 pm
MDW
-
DCA
1h 55mnonstop
Southwest Logo
6:10 am - 7:10 am
DCA
-
MDW
2h 00mnonstop
$237Southwest
Sat, Aug 8 - Sat, Aug 15
Delta Logo
6:42 pm - 10:59 pm
MDW
-
DCA
3h 17m
1 stop
Delta Logo
6:30 pm - 10:36 pm
DCA
-
MDW
5h 06m
1 stop
$238Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
6:42 pm - 11:26 pm
MDW
-
IAD
3h 44m
1 stop
Delta Logo
6:00 am - 10:10 am
IAD
-
MDW
5h 10m
1 stop
$238Delta
Wed, Aug 12 - Fri, Aug 14
United Airlines Logo
6:30 am - 9:28 am
ORD
-
IAD
1h 58mnonstop
United Airlines Logo
6:15 am - 7:30 am
IAD
-
ORD
2h 15mnonstop
$243United Airlines
Thu, Aug 20 - Mon, Aug 24
American Airlines Logo
8:00 am - 10:59 am
ORD
-
DCA
1h 59mnonstop
American Airlines Logo
1:46 pm - 3:10 pm
DCA
-
ORD
2h 24mnonstop
$246American 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 September.

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 5 days was to Staunton, at $233 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 5 days was $237.

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 $374 on average. Morning departures are around 8% 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 $406.

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 $381, 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 June and May, when the average cost of round-trip tickets is $182 and $160 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 Saturday 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 51% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$99
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Chicago O'Hare Airport to Reagan Washington National Airport

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 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.
7.9
SouthwestOverall score based on 4250 reviews
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

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.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

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.

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

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

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

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.

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

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

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

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.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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.