$89 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 9/11. 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.
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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$277
Richmond
Richmond1 stop$282
Roanoke
Roanokenonstop$279
Charlottesville
Charlottesvillenonstop$279
Raleigh
Raleigh1 stop$209
Washington, D.C.
Baltimore1 stop$141
Blountville
Blountville1 stop$242
Norfolk
Norfolk1 stop$277
Richmond
Richmond1 stop$282
Roanoke
Roanokenonstop$279
Charlottesville
Charlottesvillenonstop$279
Raleigh
Raleigh1 stop$209
Washington, D.C.
Baltimore1 stop$141
Blountville
Blountville1 stop$242

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, Oct 26 - Sat, Nov 7
Frontier Logo
9:20 am - 5:36 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
7h 16m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:00 am - 12:02 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
6h 02m1 stop Atlanta Hartsfield-Jackson
$182Frontier
Thu, Sep 3 - Tue, Sep 8
Frontier Logo
1:59 pm - 10:52 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
7h 53m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:09 pm - 3:20 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
22h 11m1 stop Fort Lauderdale
$182Frontier
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
1:20 pm - 4:15 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 55mnonstop
Southwest Logo
11:55 am - 2:15 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
3h 20m1 stop Columbus
$187Southwest
Sat, Sep 5 - Sat, Sep 5
Southwest Logo
6:00 am - 8:45 amMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 45mnonstop
Southwest Logo
3:55 pm - 7:20 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
4h 25m1 stop Nashville Intl
$187Southwest
Sat, Sep 5 - Sun, Sep 6
Delta Logo
5:45 pm - 11:26 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
4h 41m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:10 am - 9:17 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
$197Delta
Sat, Sep 5 - Sun, Sep 6
Delta Logo
4:39 pm - 12:34 amMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
6h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:10 am - 9:17 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
$197Delta
Sat, Sep 5 - Sun, Sep 6
American Airlines Logo
5:51 pm - 8:55 pmORD  Chicago O'Hare Intl-RDU Raleigh-Durham
2h 04mnonstop
American Airlines Logo
1:51 pm - 3:30 pmRDU  Raleigh-Durham-ORD Chicago O'Hare Intl
2h 39mnonstop
$209American Airlines
Tue, Oct 20 - Fri, Oct 30
United Airlines Logo
7:47 pm - 10:52 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 05mnonstop
United Airlines Logo
1:15 pm - 2:38 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 23mnonstop
$216United Airlines
Fri, Dec 25 - Thu, Dec 31
United Airlines Logo
6:07 pm - 9:08 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 01mnonstop
United Airlines Logo
3:37 pm - 4:44 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 07mnonstop
$216United Airlines
Fri, Sep 11 - Tue, Sep 15
American Airlines Logo
5:54 pm - 9:00 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 06mnonstop
American Airlines Logo
5:00 pm - 6:29 pmDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 29mnonstop
$216American 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.

Flight prices are below average for this route right now.

Flights to Virginia from Chicago usually cost between $318 and $539 in September.
The lowest price found in the past 5 days was $282 on Southwest (Sep 19-Sep 26).

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 Richmond, at $237 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 5 days was $277.

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 $383 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 $405.

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 $394, 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 October, when tickets cost $349 (return) on average. On the other hand, the most expensive months are June and April, when the average cost of round-trip tickets is $430 and $414 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 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low season

January

Cheapest flight

$89
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 13% 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 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.
8.0
SouthwestOverall score based on 4216 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

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.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

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.

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

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.

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.