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$55+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheapflights Tip: The best prices from Virginia Beach to Chicago are usually found in September or October, booked 78 days in advance, depart on a Thursday or Friday and return on a Wednesday

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 November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/158:38 amORF - ORD
2 stops16h 19mMultiple Airlines
Wed 12/171:34 pmORD - ORF
1 stop7h 29mMultiple Airlines
Deal found 11/10$195
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 11/209:26 pmORF - ORD
1 stop11h 00mMultiple Airlines
Mon 11/246:00 amORD - ORF
1 stop8h 21mMultiple Airlines
Deal found 11/11$197
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/128:11 pmORF - ORD
1 stop24h 50mMultiple Airlines
Tue 1/1310:07 amORD - ORF
1 stop26h 19mMultiple Airlines
Deal found 11/11$198
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/1212:00 pmORF - MDW
1 stop8h 42mMultiple Airlines
Tue 1/1312:25 pmMDW - ORF
2 stops24h 01mMultiple Airlines
Deal found 11/11$200
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/209:26 pmORF - ORD
1 stop11h 00mMultiple Airlines
Sun 11/236:35 pmORD - ORF
1 stop19h 46mMultiple Airlines
Deal found 11/12$201
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/128:11 pmORF - ORD
1 stop24h 50mMultiple Airlines
Wed 1/145:32 pmORD - ORF
2 stops17h 46mMultiple Airlines
Deal found 11/11$203
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/48:38 amORF - MDW
1 stop14h 20mMultiple Airlines
Sun 12/76:37 pmMDW - ORF
1 stop12h 06mMultiple Airlines
Deal found 11/12$204
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/1212:00 pmORF - MDW
1 stop8h 42mMultiple Airlines
Thu 1/156:00 amMDW - ORF
2 stops15h 26mMultiple Airlines
Deal found 11/11$205
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/128:11 pmORF - ORD
1 stop24h 50mMultiple Airlines
Thu 1/155:01 amORD - ORF
2 stops16h 25mMultiple Airlines
Deal found 11/11$206
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Sat 12/68:11 pmORF - ORD
2 stops20h 57mMultiple Airlines
Mon 12/87:10 amORD - ORF
1 stop11h 06mMultiple Airlines
Deal found 11/12$207
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/85:40 pmORF - MDW
1 stop16h 06mMultiple Airlines
Sat 12/136:00 amMDW - ORF
2 stops15h 03mMultiple Airlines
Deal found 11/12$218
This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/258:02 pmORF - ORD
1 stop14h 15mSpirit Airlines
Tue 12/26:48 amORD - ORF
1 stop12h 43mSpirit Airlines
Deal found 11/11$221

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$195
(Kiwi.com)

One-way from

$55
(Frontier)

Popular in

December

Cheapest in

September

Average price

$370
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
Search Deals
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. 6% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 13, 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 12/12

12:00 pm-7:42 pm

1 stop8h 42m

Chicago Midway

Sun 1/11

9:07 pm-10:51 am

2 stops12h 44m

$223

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 1/16

11:46 am-9:55 pm

2 stops11h 09m

Chicago O'Hare Intl

Sun 1/18

11:32 am-10:26 pm

1 stop9h 54m

$274

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 1/17

4:45 pm-6:20 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sun 1/18

11:05 am-2:25 pm

Nonstop2h 20m

$275

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 11/27

7:00 am-10:43 pm

2 stops16h 43m

Chicago Midway

Mon 12/1

5:47 pm-8:31 pm

1 stop25h 44m

$283

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 12/3

10:05 am-4:00 pm

1 stop6h 55m

Chicago Midway

Sat 12/6

1:25 pm-4:20 pm

Nonstop1h 55m

$285

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sun 2/15

7:34 am-9:25 am

Nonstop2h 51m

Chicago O'Hare Intl

Sat 2/21

1:54 pm-7:28 pm

1 stop4h 34m

$285

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 1/16

11:46 am-9:55 pm

2 stops11h 09m

Chicago O'Hare Intl

Sat 1/17

7:45 pm-12:24 pm

1 stop15h 39m

$287

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 12/10

10:38 am-4:34 pm

1 stop6h 56m

Chicago Midway

Sat 12/13

11:05 am-4:14 pm

1 stop4h 09m

$295

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 12/15

5:30 pm-6:40 pm

Nonstop2h 10m

Chicago Midway

Wed 12/17

6:05 pm-9:05 pm

Nonstop2h 00m

$295

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sun 2/15

6:00 am-9:40 am

1 stop4h 40m

Chicago O'Hare Intl

Fri 2/20

6:30 am-12:12 pm

1 stop4h 42m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 43 results
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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 November 7, 2025.

Booking 78 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, May is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $108). Flying from Virginia Beach to Chicago in July is currently the most expensive (average of $265). 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 November 13, 2025.

A simple way to save on the total cost of your ticket is to fly from Virginia Beach to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 6% on your trip compared to booking a flight in the evening.

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 November 2, 2025.

Travelers seeking maximum savings on their Virginia Beach to Chicago flight should consider departing on Saturday mornings when fares are most often at their lowest. Sunday evenings 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 November 13, 2025.

The most flights from V1B to CHI are scheduled on a Monday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 November 13, 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

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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
8,138 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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
3,110 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

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 35m. 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 $88. Southwest flights start at $138 while deals on United Airlines start at $138 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 ANA (93%), Republic Airways (92%) and United Airlines (91%).

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

    The cheapest flight price from Virginia Beach to Chicago is $115. On average you can expect to pay $1,018. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $130.

  • 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, May is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $108). Flying from Virginia Beach to Chicago in July is currently the most expensive (average of $265). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Alternative routes for Virginia Beach to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Reagan-National to Springfield 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$258FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$260FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$168Average$208FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$216Average$391FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$217Average$383FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$229Average$380FlexibilityNo cancel feeOn-time63%

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