$57 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 8/12. 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 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, Sep 24 - Mon, Sep 29
Southwest Logo
10:30 am - 1:35 pmMDW-ORF
2h 05mnonstop
Southwest Logo
5:30 am - 6:30 amORF-MDW
2h 00mnonstop
$113Southwest
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Sat, Aug 9 - Tue, Aug 12
United Airlines Logo
6:22 pm - 9:40 pmORD-ORF
2h 18mnonstop
United Airlines Logo
5:05 pm - 6:30 pmORF-ORD
2h 25mnonstop
$113United Airlines
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Tue, Aug 12 - Mon, Aug 18
Southwest Logo
7:25 am - 2:20 pmMDW-ORF
5h 55m1 stop
Southwest Logo
5:30 am - 6:30 amORF-MDW
2h 00mnonstop
$123Southwest
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Tue, Aug 12 - Mon, Aug 18
Southwest Logo
7:25 am - 5:15 pmMDW-ORF
8h 50m2 stops
Southwest Logo
5:30 am - 6:30 amORF-MDW
2h 00mnonstop
$128Southwest
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Fri, Sep 19 - Mon, Sep 22
United Airlines Logo
6:30 pm - 9:52 pmORD-ORF
2h 22mnonstop
United Airlines Logo
6:30 am - 7:54 amORF-ORD
2h 24mnonstop
$130United Airlines
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Thu, Aug 21 - Mon, Aug 25
American Airlines Logo
2:24 pm - 5:42 pmORD-ORF
2h 18mnonstop
American Airlines Logo
6:12 pm - 7:50 pmORF-ORD
2h 38mnonstop
$147American Airlines
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Thu, Sep 4 - Mon, Sep 8
American Airlines Logo
2:20 pm - 5:44 pmORD-ORF
2h 24mnonstop
American Airlines Logo
5:30 am - 12:02 pmORF-ORD
7h 32m1 stop
$166American Airlines
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Tue, Jul 29 - Tue, Aug 5
Spirit Airlines Logo
10:00 am - 10:35 pmORD-ORF
11h 35m1 stop
Spirit Airlines Logo
5:50 am - 3:31 pmORF-ORD
10h 41m1 stop
$180Spirit Airlines
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Wed, Jul 23 - Wed, Jul 30
Spirit Airlines Logo
10:00 am - 10:35 pmORD-ORF
11h 35m1 stop
Spirit Airlines Logo
5:50 am - 3:31 pmORF-ORD
10h 41m1 stop
$186Spirit Airlines
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Thu, Aug 28 - Mon, Sep 1
Frontier Logo
6:15 am - 3:18 pmMDW-ORF
8h 03m1 stop
Frontier Logo
4:12 pm - 11:27 pmORF-MDW
8h 15m1 stop
$201Frontier
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Good to know

Low seasonFebruary
High seasonJune
Cheapest flight$57
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 11% 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 1h 55m.

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

    28 direct flights run between Chicago and Virginia Beach on a daily basis. On average, there are about 196 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 Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays and the most expensive ones on Thursdays.

  • 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 72 hours, the cheapest one-way ticket between Chicago and Virginia Beach found on KAYAK was with Southwest for $57. Southwest offered a round-trip connection from $113 and United Airlines from $113.

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 73 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be May, June and July. The cheapest month to fly is September.

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

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 Beach

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