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$58+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find cheap flights from Chicago to Virginia Beach with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Virginia Beach are usually found in September or February, booked 68 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap 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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$110
(Frontier)

One-way from

$58
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$415
Provider with most accurate pricing for Chicago (CHI)-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Norfolk flights.
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From Chicago (CHI) to Virginia Beach
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One-way flight from Chicago (CHI) to Virginia Beach
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Highest demand for flights based on searches. 3% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 30, 2025.

This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:30 amMDW - ORF
1 stop6h 55mFrontier
Mon 11/1711:29 amORF - MDW
1 stop11h 42mFrontier
Deal found 10/30$110
This Priceline deal was found by Cheapflights users on 10/29. 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.
Thu 11/135:25 amORD - ORF
1 stop6h 50mFrontier
Thu 11/133:20 pmORF - ORD
1 stop9h 51mFrontier
Deal found 10/29$110
This Priceline deal was found by Cheapflights users on 10/30. 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.
Thu 11/135:25 amORD - ORF
1 stop6h 50mFrontier
Mon 11/1711:29 amORF - ORD
1 stop6h 27mFrontier
Deal found 10/30$127
This Priceline deal was found by Cheapflights users on 10/29. 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.
Thu 11/65:01 amORD - ORF
1 stop4h 45mFrontier
Thu 11/133:20 pmORF - ORD
1 stop9h 51mFrontier
Deal found 10/29$143
This Priceline deal was found by Cheapflights users on 10/29. 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.
Wed 11/1210:52 amORD - ORF
1 stop7h 06mMultiple Airlines
Thu 11/133:20 pmORF - ORD
1 stop9h 51mMultiple Airlines
Deal found 10/29$158
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:15 amMDW - ORF
1 stop9h 05mFrontier
Fri 12/1212:00 pmORF - MDW
1 stop8h 42mFrontier
Deal found 10/30$166
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 11/237:09 pmORD - ORF
1 stop13h 34mMultiple Airlines
Tue 12/29:26 pmORF - ORD
1 stop19h 37mMultiple Airlines
Deal found 10/29$167
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 11/206:23 pmORD - ORF
1 stop25h 08mMultiple Airlines
Tue 12/29:26 pmORF - ORD
1 stop19h 37mMultiple Airlines
Deal found 10/29$172
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 12/46:15 amORD - ORF
1 stop12h 01mMultiple Airlines
Thu 12/118:38 amORF - ORD
1 stop6h 43mMultiple Airlines
Deal found 10/28$174
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 11/237:09 pmORD - ORF
1 stop13h 34mMultiple Airlines
Mon 12/19:26 pmORF - ORD
1 stop26h 40mMultiple Airlines
Deal found 10/29$179
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Mon 11/246:48 amORD - ORF
1 stop12h 43mSpirit Airlines
Tue 12/29:26 pmORF - ORD
1 stop19h 37mSpirit Airlines
Deal found 10/29$181
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 11/206:23 pmORD - ORF
1 stop25h 08mMultiple Airlines
Mon 12/19:26 pmORF - ORD
1 stop26h 40mMultiple Airlines
Deal found 10/29$183

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 October 30, 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

Thu 11/13

5:11 am-2:25 pm

1 stop8h 14m

Norfolk

Mon 11/17

11:29 am-4:56 pm

1 stop6h 27m

$150

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Wed 11/12

2:06 pm-1:15 pm

2 stops22h 09m

Norfolk

Sun 11/16

9:03 pm-8:32 am

1 stop12h 29m

$187

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 12/6

7:10 am-7:16 pm

1 stop11h 06m

Norfolk

Mon 12/8

8:38 am-2:21 pm

1 stop6h 43m

$212

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 12/11

5:00 am-7:16 pm

1 stop13h 16m

Norfolk

Thu 12/18

3:01 pm-12:30 am

1 stop10h 29m

$217

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sun 1/18

2:12 pm-10:54 am

1 stop19h 42m

Norfolk

Sun 1/25

1:10 pm-11:25 pm

2 stops35h 15m

$237

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Tue 11/25

6:05 am-2:55 pm

1 stop7h 50m

Norfolk

Mon 12/1

9:26 pm-8:46 am

2 stops36h 20m

$256

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Thu 11/13

12:17 pm-6:58 pm

3 stops29h 41m

Norfolk

Mon 11/17

7:53 pm-6:34 pm

2 stops23h 41m

$256

ChicagoNorfolk

MDW - ORF

MDWORF

Chicago Midway

Sat 12/13

1:25 pm-4:20 pm

Nonstop1h 55m

Norfolk

Sat 1/10

11:15 am-4:55 pm

1 stop6h 40m

$285

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Tue 11/25

5:00 am-12:28 pm

1 stop6h 28m

Norfolk

Thu 11/27

9:56 am-2:14 pm

1 stop5h 18m

$296

ChicagoNorfolk

ORD - ORF

ORDORF

Chicago O'Hare Intl

Sat 12/6

7:10 am-2:25 pm

1 stop6h 15m

Norfolk

Mon 12/8

7:23 am-9:02 am

Nonstop2h 39m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 39 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 October 24, 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 $149). Flying from Chicago to Virginia Beach in January is currently the most expensive (average of $270). 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 October 30, 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 15% 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 October 26, 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. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago to Virginia Beach?

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 October 30, 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
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,030 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,123 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 1h 55m. Frontier provides one of the quickest options available for as low as $285. Chicago and Virginia Beach are separated by a distance of 702 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 Spirit Airlines. According to our data, you can fly for as low as $95. Users have also found prices from $114 and $129 on Frontier 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: Republic Airways (92%), Envoy Air (88%), United Airlines( 83%).

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

    Looking at all options, your cheapest flight can be booked for $115. While the most popular route (Chicago O'Hare Intl - Norfolk) can be booked for $141 on average, our data indicates $322 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 $149). Flying from Chicago to Virginia Beach in January is currently the most expensive (average of $270). 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.
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$218Average$424FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$230Average$363FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$237Average$395FlexibilityNo cancel feeOn-time71%

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