$115 Find Cheap Flights from Chicago to Virginia Beach

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 Beach departing on 8/25. 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

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Everything you should know

Cheapest round-trip
$310
Typical prices: $488-$359
Frontier
Wed 6/10Tue 6/16
ORD - ORF • 1 stop
Cheapest non-stop
$317
Typical prices: $501-$364
American Airlines
Wed 6/17Tue 6/23
ORD - ORF • Non-stop
Arrival airport
You can't fly directly to Virginia Beach. It is served by Norfolk (ORF), located 12.6 miles from Virginia Beach.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Virginia Beach (CHI-ORF)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Virginia Beach 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 Beach

Wed, Jun 10 - Tue, Jun 16
Frontier Logo
4:59 pm - 8:40 pm
ORD
-
ORF
26h 41m
1 stop
Frontier Logo
12:21 pm - 7:50 pm
ORF
-
ORD
8h 29m
1 stop
$310Frontier
Thu, Jun 25 - Wed, Jul 1
Frontier Logo
4:59 pm - 8:40 pm
ORD
-
ORF
26h 41m
1 stop
Frontier Logo
12:21 pm - 7:50 pm
ORF
-
ORD
8h 29m
1 stop
$314Frontier
Wed, Jun 17 - Wed, Jun 24
United Airlines Logo
6:15 pm - 9:37 pm
ORD
-
ORF
2h 22mnonstop
United Airlines Logo
8:00 am - 9:32 am
ORF
-
ORD
2h 32mnonstop
$317United Airlines
Sun, Jul 12 - Sun, Jul 19
Frontier Logo
5:13 pm - 8:39 pm
ORD
-
ORF
26h 26m
1 stop
Frontier Logo
9:34 pm - 9:11 am
ORF
-
ORD
12h 37m
1 stop
$323Frontier
Fri, Aug 28 - Sun, Sep 6
Multiple Airlines Logo
7:55 am - 11:08 pm
ORD
-
ORF
14h 13m
2 stops
Multiple Airlines Logo
9:56 pm - 11:14 pm
ORF
-
ORD
26h 18m
1 stop
$324Multiple Airlines
Thu, Jun 25 - Wed, Jul 1
Frontier Logo
4:59 pm - 8:40 pm
ORD
-
ORF
26h 41m
1 stop
Frontier Logo
12:21 pm - 7:50 pm
ORF
-
ORD
8h 29m
1 stop
$325Frontier
Tue, Jun 23 - Tue, Jun 23
American Airlines Logo
8:00 am - 1:46 pm
ORD
-
ORF
4h 46m
1 stop
American Airlines Logo
6:29 pm - 8:15 pm
ORF
-
ORD
2h 46mnonstop
$327American Airlines
Tue, Jun 30 - Tue, Jul 7
Southwest Logo
6:50 pm - 9:50 pm
MDW
-
ORF
2h 00mnonstop
Southwest Logo
4:30 pm - 9:40 pm
ORF
-
MDW
6h 10m
1 stop
$327Southwest
Thu, Jun 18 - Sun, Jun 21
Frontier Logo
4:59 pm - 8:40 pm
ORD
-
ORF
26h 41m
1 stop
Frontier Logo
9:35 pm - 9:21 am
ORF
-
ORD
12h 46m
1 stop
$328Frontier
Tue, Jun 30 - Tue, Jul 7
Southwest Logo
10:10 am - 6:20 pm
MDW
-
ORF
7h 10m
2 stops
Southwest Logo
7:00 pm - 8:10 pm
ORF
-
MDW
2h 10mnonstop
$332Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$115
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago Midway Airport to Norfolk

When to book flights from Chicago to Virginia Beach

Are your dates flexible? Find out the best times to travel from Chicago to Virginia Beach based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Virginia Beach

  • Which airports will I be using when flying from Chicago to Virginia Beach?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Virginia Beach does not have its own airport so you’ll be flying into nearby Norfolk airport, which is 12.6 mi away.

  • How long does a flight from Chicago to Virginia Beach take?

    Direct flights cover the 699 miles separating Chicago and Virginia Beach in about 2h 00m.

  • How many flights are there between Chicago and Virginia Beach?

    29 direct flights run between Chicago and Virginia Beach on a daily basis. On average, there are about 209 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Virginia Beach?

    Consider leaving on a Wednesday and avoid Thursdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Sundays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Virginia Beach?

    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 Beach.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Virginia Beach from Chicago 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 Beach?

    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 to Virginia Beach with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Virginia Beach?

    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 to Virginia Beach from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Virginia Beach?

    In the last 5 days, the cheapest one-way ticket between Chicago and Virginia Beach found on KAYAK was with Frontier for $72. United Airlines offered a round-trip connection from $217 and Southwest from $230.

Top tips for finding cheap flights from Chicago to Virginia Beach

  • There is no airport in Virginia Beach. Instead, you’ll be flying into Norfolk Airport when flying between Chicago and Virginia Beach.
  • The cheapest flight from Chicago to Virginia Beach was found 61 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly is December.

Reviews of the top 4 airlines serving Chicago to Virginia Beach

 
Need help choosing which airline to fly with from Chicago to Virginia Beach? 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 4258 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
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!

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

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.

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 Beach

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