$70 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 5/15. 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
$297
Typical prices: $469-$368
Southwest
Thu 6/18Mon 6/22
MDW - ORF • Non-stop
Cheapest one-way
$70
Typical prices: $179-$297
Frontier
Fri 5/15
MDW - ORF • 1 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

Thu, Jun 18 - Mon, Jun 22
Southwest Logo
7:40 am - 10:45 am
MDW
-
ORF
2h 05mnonstop
Southwest Logo
7:15 pm - 8:20 pm
ORF
-
MDW
2h 05mnonstop
$297Southwest
Mon, May 18 - Sat, May 23
United Airlines Logo
1:55 pm - 5:19 pm
ORD
-
ORF
2h 24mnonstop
United Airlines Logo
5:02 pm - 6:34 pm
ORF
-
ORD
2h 32mnonstop
$297United Airlines
Fri, May 29 - Fri, Jun 5
Multiple Airlines Logo
8:05 am - 5:39 pm
ORD
-
ORF
8h 34m
1 stop
Multiple Airlines Logo
12:06 pm - 7:51 pm
ORF
-
ORD
8h 45m
1 stop
$298Multiple Airlines
Thu, May 7 - Mon, May 11
American Airlines Logo
7:10 pm - 10:33 pm
ORD
-
ORF
2h 23mnonstop
American Airlines Logo
8:01 pm - 9:42 pm
ORF
-
ORD
2h 41mnonstop
$299American Airlines
Thu, Apr 30 - Fri, May 1
Spirit Airlines Logo
11:28 am - 5:04 pm
ORD
-
ORF
28h 36m
3 stops
Spirit Airlines Logo
8:57 pm - 9:12 pm
ORF
-
ORD
25h 15m
2 stops
$300Spirit Airlines
Fri, May 15 - Sun, May 17
Spirit Airlines Logo
7:33 pm - 6:49 pm
ORD
-
ORF
22h 16m
2 stops
Spirit Airlines Logo
6:34 pm - 12:23 pm
ORF
-
ORD
18h 49m
2 stops
$301Spirit Airlines
Tue, May 12 - Tue, May 19
United Airlines Logo
5:45 pm - 9:04 pm
ORD
-
ORF
2h 19mnonstop
United Airlines Logo
6:00 am - 7:30 am
ORF
-
ORD
2h 30mnonstop
$303United Airlines
Thu, May 14 - Thu, May 21
Frontier Logo
12:19 pm - 8:17 pm
MDW
-
ORF
30h 58m
2 stops
Frontier Logo
12:06 pm - 10:02 pm
ORF
-
MDW
10h 56m
1 stop
$304Frontier
Fri, Jul 3 - Mon, Jul 6
Frontier Logo
1:50 pm - 11:21 am
ORD
-
ORF
20h 31m
1 stop
Frontier Logo
9:56 pm - 4:10 pm
ORF
-
ORD
19h 14m
2 stops
$305Frontier
Thu, Jun 18 - Mon, Jun 22
Southwest Logo
7:00 pm - 11:35 pm
MDW
-
ORF
3h 35m
1 stop
Southwest Logo
7:05 am - 8:10 am
ORF
-
MDW
2h 05mnonstop
$307Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$70
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 1% 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?

    37 direct flights run between Chicago and Virginia Beach on a daily basis. On average, there are about 260 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 Fridays 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 72 hours, the cheapest one-way ticket between Chicago and Virginia Beach found on KAYAK was with Frontier for $93. 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 72 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 4330 reviews
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

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!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

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.

Pretty awful. 2 hours late due to operational issues and finally deboarded around 2am.

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.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

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.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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 !!!!!!!

The flight never took off and we spent 7 hours at the airport

Everything you need to know for your flight from Chicago to Virginia Beach

Complete your trip to Virginia Beach with a hotel stay or car rental