HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$72+ Cheap flights from Virginia Beach, VA to Chicago (CHI)

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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Virginia Beach to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Virginia Beach to Chicago are usually found in October or March, booked 10 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap flight deals from Virginia Beach to Chicago

Keep the following information in mind while searching for Virginia Beach to Chicago flight deals. Data was last updated September 16, 2025.

Round-trip from

$217
(CheapOair)

One-way from

$72
(Priceline)

Popular in

January

Cheapest in

October

Average price

$361
From Virginia Beach to Chicago (CHI)
Search Deals
One-way flight from Virginia Beach to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Virginia Beach to Chicago

Cheapest flights from Virginia Beach to Chicago
Explore the most affordable flight options available from Virginia Beach to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:00 amORF - ORD
1 stop13h 23mSpirit Airlines
Mon 11/1010:18 amORD - ORF
1 stop12h 49mSpirit Airlines
Deal found 9/16$217
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:38 pmORF - MDW
1 stop17h 43mMultiple Airlines
Sun 10/510:13 amMDW - ORF
1 stop29h 26mMultiple Airlines
Deal found 9/16$219
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 12/128:32 pmORF - ORD
1 stop23h 12mMultiple Airlines
Mon 12/1510:18 amORD - ORF
1 stop8h 19mMultiple Airlines
Deal found 9/15$219
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/175:38 pmORF - MDW
1 stop17h 43mMultiple Airlines
Sun 10/196:20 amMDW - ORF
1 stop7h 34mMultiple Airlines
Deal found 9/15$220
This Trip.com deal was found by Cheapflights users on 9/15. 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.
Thu 9/255:12 pmORF - ORD
1 stop27h 32mFrontier
Mon 9/295:10 amORD - ORF
1 stop5h 14mFrontier
Deal found 9/15$221
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/28:01 amORF - ORD
1 stop14h 22mMultiple Airlines
Fri 12/56:05 amORD - ORF
1 stop15h 15mMultiple Airlines
Deal found 9/16$222
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/305:24 amORF - ORD
2 stops9h 35mMultiple Airlines
Mon 11/35:15 amORD - ORF
1 stop10h 24mMultiple Airlines
Deal found 9/15$223
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/301:06 pmORF - ORD
2 stops11h 22mFrontier
Thu 11/65:25 amORD - ORF
1 stop5h 56mFrontier
Deal found 9/15$224
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:01 amORF - MDW
1 stop15h 19mMultiple Airlines
Sun 11/910:12 amMDW - ORF
1 stop12h 55mMultiple Airlines
Deal found 9/16$226
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/245:38 pmORF - ORD
1 stop23h 01mMultiple Airlines
Mon 10/278:15 amORD - ORF
1 stop7h 24mMultiple Airlines
Deal found 9/15$226
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 11/611:41 amORF - MDW
1 stop11h 22mMultiple Airlines
Sun 11/910:12 amMDW - ORF
1 stop12h 55mMultiple Airlines
Deal found 9/15$227
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 10/275:24 amORF - ORD
2 stops32h 29mMultiple Airlines
Mon 11/35:15 amORD - ORF
1 stop10h 24mMultiple Airlines
Deal found 9/14$228

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia Beach to Chicago 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 September 16, 2025.
Use the filters below to find and compare flights from Virginia Beach to Chicago that are best for you.

Fly from

Virginia Beach

Fly to

Chicago

Route

Depart

Return

Price

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 11/7

11:43 am-10:20 pm

2 stops11h 37m

Chicago Midway

Sun 11/9

10:12 am-12:07 am

1 stop12h 55m

$240

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 10/3

5:20 am-10:52 am

1 stop6h 32m

Chicago O'Hare Intl

Sat 10/4

11:57 am-10:48 pm

1 stop9h 51m

$254

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 10/3

12:19 pm-10:28 am

2 stops23h 09m

Chicago Midway

Sun 10/5

10:13 am-4:57 pm

1 stop5h 44m

$255

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 12/2

8:32 pm-9:00 pm

2 stops25h 28m

Chicago O'Hare Intl

Fri 12/5

6:05 am-7:37 pm

1 stop12h 32m

$260

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 10/11

4:56 pm-6:21 pm

Nonstop2h 25m

Chicago O'Hare Intl

Tue 10/14

11:20 am-2:40 pm

Nonstop2h 20m

$275

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 9/29

7:00 am-12:41 pm

1 stop6h 41m

Chicago Midway

Thu 10/2

6:20 am-3:53 pm

2 stops8h 33m

$291

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 10/13

12:45 pm-2:18 pm

Nonstop2h 33m

Chicago O'Hare Intl

Wed 10/15

11:20 am-2:40 pm

Nonstop2h 20m

$294

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 3/3

5:45 am-8:50 am

1 stop4h 05m

Chicago Midway

Wed 3/4

10:35 am-4:59 pm

1 stop5h 24m

$295

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 10/28

12:22 pm-6:49 pm

1 stop7h 27m

Chicago O'Hare Intl

Sat 11/1

4:09 pm-9:33 pm

1 stop4h 24m

$295

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 10/4

6:05 pm-10:14 pm

1 stop5h 09m

Chicago O'Hare Intl

Tue 10/7

12:30 pm-6:00 pm

1 stop4h 30m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 46 results
1
2
3
...
5

Best time to book a flight from Virginia Beach to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Virginia Beach 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 Virginia Beach to Chicago

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

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

Booking 10 days in advance of your planned departure date is, on average, the best time to get cheap flights from Virginia Beach to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, August is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $245). Flying from Virginia Beach to Chicago in March is currently the most expensive (average of $321). 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 V1B to CHI?

Find hourly flight availability from Virginia Beach to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Virginia Beach to Chicago as you normally would.

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

Use this chart to determine the cheapest time to fly round-trip from Virginia Beach to Chicago. Price data was last updated on September 14, 2025.

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

Weekly flight availability from Virginia Beach to Chicago

Explore weekly flight availability from Virginia Beach to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 16, 2025.

The most flights from V1B to CHI are scheduled on a Monday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 16, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Virginia Beach to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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 Virginia Beach to Chicago. 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 Virginia Beach to Chicago?

    Departing from Virginia Beach to Chicago will take you 2h 25m. The distance between Virginia Beach and Chicago is about 715 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $78. JetBlue flights start at $124 while deals on United Airlines start at $133 one-way.

  • What are the most popular routes from Virginia Beach to Chicago?

    The most popular route from Virginia Beach to Chicago is Norfolk - Chicago O'Hare Intl. You may also consider Norfolk - Chicago Midway or Norfolk - Chicago Greater Rockford.

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

    The top 3 most reliable airlines when flying from Virginia Beach to Chicago are Emirates (100%), Avianca (89%) and United Airlines (86%).

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

    The cheapest flight price from Virginia Beach to Chicago is $135. On average you can expect to pay $901. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $161.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Virginia Beach to Chicago 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 Virginia Beach to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $245). Flying from Virginia Beach to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Virginia Beach to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Reagan-National to Midway flights
Reagan-National to St. Louis flights
Dulles Intl to St. Louis flights
Richmond to O'Hare Intl flights
Raleigh to Midway flights
Norfolk to O'Hare Intl flights
Greensboro to O'Hare Intl flights
Roanoke to O'Hare Intl flights
Charlottesville to O'Hare Intl flights
Richmond to Midway flights
Norfolk to Midway flights
Raleigh to St. Louis flights
Roanoke to Midway flights
Greensboro to Midway flights
Charlottesville to Midway flights
Richmond to St. Louis flights
Norfolk to St. Louis flights
Dulles Intl to Moline flights
Greensboro to St. Louis flights
Roanoke to St. Louis flights
Charlottesville to Peoria flights
Norfolk to Evansville flights
Dulles Intl to Peoria flights
Raleigh to Moline flights
Roanoke to Moline flights
Roanoke to Peoria flights
Reagan-National to Peoria flights
Raleigh to Peoria flights
Blountville to O'Hare Intl flights
Reagan-National to Moline flights
Richmond to Moline flights
Lewisburg to O'Hare Intl flights
Raleigh to Evansville flights
Reagan-National to Bloomington flights
Greensboro to Moline flights
Norfolk to Moline flights
Charlottesville to St. Louis flights
Dulles Intl to Bloomington flights
Richmond to Evansville flights
Charlottesville to Moline flights
Reagan-National to Evansville flights
Dulles Intl to Evansville flights
Lynchburg to Peoria flights
Reagan-National to Champaign flights
Charlottesville to Bloomington flights

Top 6 airlines flying from Virginia Beach to Chicago

Discover the top 6 airlines that operate flights from Virginia Beach to Chicago. 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$270FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$352FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$168Average$204FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$208Average$383FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$238Average$392FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$383FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.