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$58+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
nov. 22 — nov. 291
sáb. 11/22
sáb. 11/29
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 10 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 octubre 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
vie. 11/77:53 pmORF - ORD
1 stop16h 19mSpirit Airlines
mar. 11/117:34 pmORD - ORF
2 stops21h 04mSpirit Airlines
Deal found 10/22$214
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
jue. 11/209:26 pmORF - ORD
1 stop11h 00mMultiple Airlines
jue. 11/272:01 pmORD - ORF
1 stop7h 28mMultiple Airlines
Deal found 10/22$216
This United Airlines deal was found by Cheapflights users on 10/22. 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.
vie. 12/128:10 pmORF - ORD
1 stop4h 34mUnited Airlines
dom. 12/1411:20 amORD - ORF
Nonstop2h 14mUnited Airlines
Deal found 10/22$217
This Mytrip deal was found by Cheapflights users on 10/21. 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.
mar. 11/116:33 pmORF - ORD
2 stops20h 58mSpirit Airlines
mié. 11/127:34 pmORD - ORF
2 stops23h 34mSpirit Airlines
Deal found 10/21$218
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/106:15 pmORF - MDW
1 stop3h 50mSouthwest
vie. 12/127:25 pmMDW - ORF
Nonstop2h 00mSouthwest
Deal found 10/20$221
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
mar. 11/258:02 pmORF - ORD
2 stops53h 06mMultiple Airlines
lun. 12/16:15 pmORD - ORF
1 stop25h 16mMultiple Airlines
Deal found 10/21$222
This American Airlines deal was found by Cheapflights users on 10/23. 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.
vie. 12/123:13 pmORF - ORD
Nonstop2h 42mAmerican Airlines
lun. 12/157:30 amORD - ORF
Nonstop2h 15mAmerican Airlines
Deal found 10/23$224
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
vie. 11/77:53 pmORF - ORD
2 stops16h 37mMultiple Airlines
lun. 11/103:26 pmORD - ORF
1 stop26h 32mMultiple Airlines
Deal found 10/20$225
This Delta deal was found by Cheapflights users on 10/22. 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.
lun. 11/245:15 amORF - MDW
1 stop5h 37mDelta
mié. 12/36:00 amMDW - ORF
1 stop7h 09mDelta
Deal found 10/22$227
This Mytrip deal was found by Cheapflights users on 10/20. 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.
jue. 11/67:53 pmORF - ORD
1 stop16h 19mSpirit Airlines
mar. 11/118:28 amORD - ORF
3 stops33h 30mSpirit Airlines
Deal found 10/20$227
This Delta deal was found by Cheapflights users on 10/22. 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.
sáb. 12/612:12 pmORF - MDW
1 stop4h 32mDelta
dom. 12/76:00 amMDW - ORF
1 stop7h 09mDelta
Deal found 10/22$228
This Southwest deal was found by Cheapflights users on 10/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/165:30 pmORF - MDW
Nonstop2h 10mSouthwest
jue. 12/187:25 pmMDW - ORF
Nonstop2h 00mSouthwest
Deal found 10/23$229

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 octubre 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$214
(Kiwi.com)

One-way from

$58
(Priceline)

Popular in

December

Cheapest in

September

Average price

$313
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 ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 octubre 23, 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

mié. 12/10

6:15 pm-9:05 pm

1 stop3h 50m

Chicago Midway

vie. 12/12

7:25 pm-10:25 pm

Nonstop2h 00m

$221

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

sáb. 12/6

12:12 pm-3:44 pm

1 stop4h 32m

Chicago Midway

dom. 12/7

6:00 am-2:09 pm

1 stop7h 09m

$228

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

vie. 11/7

7:53 pm-11:12 am

1 stop16h 19m

Chicago O'Hare Intl

mar. 11/11

8:28 am-6:58 pm

3 stops33h 30m

$228

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

mié. 11/5

6:33 pm-9:12 am

1 stop15h 39m

Chicago Midway

sáb. 11/8

1:37 pm-12:16 pm

2 stops21h 39m

$244

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

sáb. 12/6

5:30 pm-6:40 pm

Nonstop2h 10m

Chicago Midway

dom. 12/7

7:25 pm-10:25 pm

Nonstop2h 00m

$244

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

jue. 11/20

9:26 pm-7:26 am

1 stop11h 00m

Chicago O'Hare Intl

dom. 11/30

7:09 pm-9:43 am

1 stop13h 34m

$249

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mié. 11/26

4:52 pm-6:20 pm

Nonstop2h 28m

Chicago O'Hare Intl

jue. 1/1

7:25 am-10:38 am

Nonstop2h 13m

$254

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mié. 11/26

8:02 pm-2:31 pm

2 stops19h 29m

Chicago O'Hare Intl

lun. 12/1

9:22 pm-8:31 pm

2 stops22h 09m

$258

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

mié. 12/24

1:05 pm-2:39 pm

Nonstop2h 34m

Chicago O'Hare Intl

sáb. 1/3

7:25 am-10:38 am

Nonstop2h 13m

$261

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

vie. 12/26

1:05 pm-2:39 pm

Nonstop2h 34m

Chicago O'Hare Intl

mié. 1/7

11:05 am-2:25 pm

Nonstop2h 20m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 45 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 October 17, 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, 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 December is currently the most expensive (average of $306). 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 octubre 23, 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 7% 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 October 19, 2025.

Travelers seeking maximum savings on their Virginia Beach to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Monday 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 octubre 23, 2025.

The most flights from V1B to CHI are scheduled on a Thursday (28 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 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 octubre 23, 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
4,236 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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
8,995 reviews
Southwest
8.0
Very good
4,236 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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
11,033 reviews
Southwest
8.0
Very good
4,236 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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
8,104 reviews
Southwest
8.0
Very good
4,236 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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
3,128 reviews
Southwest
8.0
Very good
4,236 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

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 3h 50m. The distance between Virginia Beach and Chicago is about 702 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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%), GoJet (94%) and ANA (93%).

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

    The cheapest flight price from Virginia Beach to Chicago is $120. On average you can expect to pay $921. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $145.

  • 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 December is currently the most expensive (average of $306). 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
Porter
Benton Harbor

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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.
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
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Top 5 airlines flying from Virginia Beach to Chicago

Discover the top 5 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 octubre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$283FlexibilityNo cancel feeOn-time65%
FrontierCheapest$168Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$385FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$392FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$229Average$381FlexibilityNo cancel feeOn-time63%

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