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$59+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 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 11, 2025.

Round-trip from

$218
(Kiwi.com)

One-way from

$59
(Southwest)

Popular in

January

Cheapest in

September

Average price

$302
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. 5% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/255:12 pmORF - ORD
2 stops31h 58mFrontier
Sun 9/285:10 amORD - ORF
1 stop5h 09mFrontier
Deal found 9/11$218
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/159:45 amORF - MDW
2 stops8h 05mSouthwest
Sat 10/188:20 amMDW - ORF
2 stops5h 40mSouthwest
Deal found 9/10$219
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:30 amORF - ORD
Nonstop2h 24mUnited Airlines
Sun 10/56:15 pmORD - ORF
Nonstop2h 23mUnited Airlines
Deal found 9/11$219
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/111:45 amORF - MDW
1 stop5h 40mSouthwest
Sat 10/410:00 amMDW - ORF
2 stops12h 00mSouthwest
Deal found 9/10$220
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:00 amORF - ORD
1 stop6h 55mAmerican Airlines
Wed 10/229:05 amORD - ORF
Nonstop2h 18mAmerican Airlines
Deal found 9/10$220
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Sun 9/285:47 pmORF - ORD
1 stop26h 57mFrontier
Thu 10/25:10 amORD - ORF
1 stop5h 14mFrontier
Deal found 9/11$221
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Sat 10/47:00 amORF - MDW
2 stops17h 41mMultiple Airlines
Sun 10/510:13 amMDW - ORF
1 stop5h 44mMultiple Airlines
Deal found 9/11$222
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 9/265:38 pmORF - ORD
1 stop22h 39mMultiple Airlines
Tue 9/306:44 pmORD - ORF
1 stop27h 04mMultiple Airlines
Deal found 9/11$222
This United Airlines deal was found by Cheapflights users on 9/9. 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.
Thu 10/306:35 amORF - ORD
Nonstop2h 26mUnited Airlines
Sun 11/25:00 amORD - ORF
1 stop6h 58mUnited Airlines
Deal found 9/9$223
This Expedia deal was found by Cheapflights users on 9/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/711:43 amORF - ORD
1 stop6h 13mMultiple Airlines
Mon 11/1010:49 amORD - ORF
1 stop11h 51mMultiple Airlines
Deal found 9/11$224
This Orbitz deal was found by Cheapflights users on 9/10. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:20 amORF - ORD
1 stop13h 19mMultiple Airlines
Sun 9/285:10 amORD - ORF
1 stop5h 09mMultiple Airlines
Deal found 9/10$225
This CheapOair deal was found by Cheapflights users on 9/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:01 amORF - ORD
1 stop10h 03mSpirit Airlines
Mon 11/1010:49 amORD - ORF
1 stop11h 51mSpirit Airlines
Deal found 9/10$226

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 11, 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

Wed 10/15

9:45 am-4:50 pm

2 stops8h 05m

Chicago Midway

Sat 10/18

8:20 am-3:00 pm

2 stops5h 40m

$219

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 10/10

12:45 pm-2:18 pm

Nonstop2h 33m

Chicago O'Hare Intl

Mon 10/13

11:20 am-2:40 pm

Nonstop2h 20m

$219

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 10/3

4:56 pm-6:21 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sun 10/5

7:10 am-10:42 am

Nonstop2h 32m

$219

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 10/9

4:56 pm-6:21 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sun 10/12

6:15 pm-9:38 pm

Nonstop2h 23m

$219

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 10/17

6:30 am-7:55 am

Nonstop2h 25m

Chicago O'Hare Intl

Sun 10/19

7:10 am-10:42 am

Nonstop2h 32m

$219

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 10/9

6:30 am-7:54 am

Nonstop2h 24m

Chicago O'Hare Intl

Mon 10/13

11:20 am-2:40 pm

Nonstop2h 20m

$219

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 10/2

4:56 pm-6:21 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sun 10/5

7:10 am-10:42 am

Nonstop2h 32m

$219

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 10/16

4:56 pm-6:21 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sun 10/19

7:10 am-10:42 am

Nonstop2h 32m

$219

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 11/5

10:24 am-2:57 pm

1 stop5h 33m

Chicago O'Hare Intl

Sun 11/9

8:36 am-11:47 am

Nonstop2h 11m

$222

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 10/21

6:25 pm-7:35 pm

Nonstop2h 10m

Chicago Midway

Fri 10/24

7:00 pm-10:00 pm

Nonstop2h 00m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 38 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 August 29, 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 11, 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 7, 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 11, 2025.

The most flights from V1B to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 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 11, 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
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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 33m. 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 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 Avianca (87%), United Airlines (85%) and Republic Airways (83%).

  • 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 $916. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $117.

  • 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

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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.
Reagan-National to O'Hare Intl flights
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Greensboro to Moline flights
Staunton to O'Hare Intl flights
Charlottesville to St. Louis flights
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Richmond to Bloomington flights
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Richmond to Peoria flights
Reagan-National to Champaign flights
Charlottesville to Bloomington flights
Richmond to Evansville 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$274FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$393FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$198Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$208Average$383FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$238Average$393FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$383FlexibilityNo cancel feeOn-time63%

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