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Virginia Beach

$56+ Cheap flights from Chicago (CHI) to Virginia Beach, VA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
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Find cheap flights from Chicago to Virginia Beach with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Virginia Beach are usually found in September or October, booked 70 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Virginia Beach

Cheapest flights from Chicago to Virginia Beach
Explore the most affordable flight options available from Chicago to Virginia Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 17, 2025.

This Priceline deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:00 amORD - ORF
1 stop6h 09mFrontier
Fri 12/262:34 pmORF - ORD
1 stop8h 50mFrontier
Deal found 12/14$337
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:25 amORD - ORF
Nonstop2h 13mUnited Airlines
Sun 1/46:30 amORF - ORD
Nonstop2h 35mUnited Airlines
Deal found 12/16$421
This Kiwi.com deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:15 pmORD - ORF
2 stops20h 17mMultiple Airlines
Wed 12/315:46 pmORF - ORD
1 stop7h 10mMultiple Airlines
Deal found 12/17$437
This Delta deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:22 pmORD - ORF
1 stop7h 30mDelta
Mon 12/297:38 pmORF - ORD
1 stop5h 24mDelta
Deal found 12/16$463
This Kiwi.com deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:00 amORD - ORF
1 stop29h 06mMultiple Airlines
Sat 1/39:39 pmORF - ORD
2 stops14h 59mMultiple Airlines
Deal found 12/15$464
This Priceline deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:00 amORD - ORF
1 stop6h 09mFrontier
Mon 12/292:04 pmORF - ORD
1 stop9h 20mFrontier
Deal found 12/14$472
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/252:50 pmORD - ORF
Nonstop2h 13mAmerican Airlines
Mon 12/297:23 amORF - ORD
Nonstop2h 32mAmerican Airlines
Deal found 12/16$478
This United Airlines deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:53 pmORD - ORF
1 stop6h 26mUnited Airlines
Sat 1/35:15 pmORF - ORD
Nonstop2h 40mUnited Airlines
Deal found 12/15$479
This Kiwi.com deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:14 amMDW - ORF
2 stops30h 52mMultiple Airlines
Sat 1/33:01 pmORF - MDW
1 stop6h 52mMultiple Airlines
Deal found 12/14$501
This Kiwi.com deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:14 amMDW - ORF
1 stop27h 18mFrontier
Sat 1/33:01 pmORF - MDW
1 stop6h 52mFrontier
Deal found 12/14$502
This Trip.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:12 amMDW - ORF
1 stop6h 27mFrontier
Mon 12/292:04 pmORF - MDW
1 stop9h 08mFrontier
Deal found 12/16$509
This Trip.com deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:12 amMDW - ORF
1 stop6h 27mFrontier
Tue 12/303:11 pmORF - MDW
1 stop7h 47mFrontier
Deal found 12/15$510

Find flight deals from Chicago to Virginia Beach

Keep the following information in mind while searching for Chicago to Virginia Beach flight deals. Data was last updated December 17, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$122
(Kiwi.com)

One-way from

$56
(Spirit)

Popular in

April

Cheapest in

September

Average price

$380
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Norfolk flights.
Search Deals
From Chicago (CHI) to Virginia Beach
Search Deals
One-way flight from Chicago (CHI) to Virginia Beach
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Virginia Beach that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 17, 2025.
Use the filters below to find and compare flights from Chicago to Virginia Beach that are best for you.

Fly from

Chicago

Fly to

Virginia Beach

Route

Depart

Return

Price

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Fri 1/16

5:15 am-6:38 pm

1 stop12h 23m

Norfolk

Mon 1/19

7:33 pm-11:22 am

1 stop16h 49m

$174

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 1/24

12:44 pm-9:50 pm

1 stop8h 06m

Norfolk

Mon 2/2

11:43 am-10:46 pm

1 stop12h 03m

$186

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 1/8

6:10 am-9:50 pm

2 stops14h 40m

Norfolk

Mon 1/12

6:45 am-11:09 pm

1 stop17h 24m

$194

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sun 2/22

10:44 am-9:50 pm

1 stop10h 06m

Norfolk

Thu 2/26

6:45 am-5:46 pm

1 stop12h 01m

$200

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 2/20

6:00 am-6:26 pm

2 stops11h 26m

Norfolk

Sun 2/22

6:45 am-2:26 pm

1 stop8h 41m

$205

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 1/24

12:44 pm-9:50 pm

1 stop8h 06m

Norfolk

Sun 2/1

11:43 am-10:46 pm

1 stop12h 03m

$205

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Wed 1/7

5:00 am-2:06 pm

1 stop8h 06m

Norfolk

Thu 1/8

7:33 pm-10:42 pm

3 stops28h 09m

$211

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 1/22

5:01 pm-10:48 am

1 stop16h 47m

Norfolk

Sun 1/25

11:43 am-10:19 pm

1 stop11h 36m

$214

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Fri 1/23

1:00 pm-9:50 pm

1 stop7h 50m

Norfolk

Sun 1/25

9:37 pm-11:45 am

2 stops15h 08m

$217

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Thu 1/8

6:10 am-6:38 pm

2 stops11h 28m

Norfolk

Sun 1/11

2:29 pm-10:59 pm

1 stop9h 30m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 42 results
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Best time to book a flight from Chicago to Virginia Beach

Have a flexible travel schedule? Discover the best time to fly to Virginia Beach from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Virginia Beach?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Virginia Beach. Price data was last updated on December 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Virginia Beach, you should look to book at least 68 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Virginia Beach?

Currently, February is the cheapest month in which you can book a flight from Chicago to Virginia Beach (average of $121). Flying from Chicago to Virginia Beach in December is currently the most expensive (average of $266). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to V1B?

Find hourly flight availability from Chicago to Virginia Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 17, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Virginia Beach in the evening. If you’re flexible enough to do this you can expect to save up to 16% on your trip compared to booking a flight in the afternoon.

What is the cheapest day to fly from Chicago to Virginia Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Virginia Beach. Price data was last updated on December 13, 2025.

Travelers seeking maximum savings on their Chicago to Virginia Beach flight should consider departing on Sunday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Virginia Beach

Get insights into the airlines that provide service to Virginia Beach. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Virginia Beach. Reviews last updated December 17, 2025.
Read through reviews of airlines operating flights from Chicago to Virginia Beach, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,049 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,082 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Chicago to Virginia Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Virginia Beach?

    A quick flight from Chicago to Virginia Beach can take about 12h 23m. Spirit Airlines provides one of the quickest options available for as low as $174. Chicago and Virginia Beach are separated by a distance of 715 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Virginia Beach one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $93. Users have also found prices from $115 and $132 on American Airlines and United Airlines, respectively.

  • What are the most reliable airlines from Chicago to Virginia Beach?

    Before booking your flight to Virginia Beach from Chicago, check out the most reliable airlines to get you to your destination on time: GoJet (73%), United Airlines (69%), Qatar Airways( 65%).

  • What are the cheapest flights from Chicago to Virginia Beach?

    Looking at all options, your cheapest flight can be booked for $119. While the most popular route (Chicago O'Hare Intl - Norfolk) can be booked for $127 on average, our data indicates $412 when flying from Chicago to Virginia Beach.

  • Can I find deals for flights from Chicago to Virginia Beach that include hotel bookings?

    Yes. In addition to deals on Chicago to Virginia Beach flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Virginia Beach?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Virginia Beach.

  • Can I find deals for business class flights from Chicago to Virginia Beach?

    Yes. Cheapflights offers flight deals from Chicago to Virginia Beach by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Virginia Beach?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Virginia Beach (average of $121). Flying from Chicago to Virginia Beach in December is currently the most expensive (average of $266). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Virginia Beach

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Reagan-National flights
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Midway to Reagan-National flights
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Top 4 airlines flying from Chicago to Virginia Beach

Discover the top 4 airlines that operate flights from Chicago to Virginia Beach. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$207Average$400FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$213Average$369FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$235Average$394FlexibilityNo cancel feeOn-time71%

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