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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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Virginia Beach to Chicago are usually found in March or April, booked 36 days in advance, depart on a Wednesday or Saturday and return on a Tuesday

Cheap flight deals from Virginia Beach to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Virginia Beach (V1B) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$264
(FlightHub)

One-way from

$55
(Frontier)

Popular in

June

Cheapest in

March

Average price

$388
From Virginia Beach to Chicago (CHI)
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One-way flight from Virginia Beach to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($12 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 January 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 January 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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.
Wed 2/194:29 pmORF - ORD
1 stop8h 29mSpirit Airlines
Wed 2/2611:35 amORD - ORF
3 stops34h 46mSpirit Airlines
Deal found 1/20$259
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/225:28 amORF - ORD
1 stop11h 29mMultiple Airlines
Sat 4/264:30 pmORD - ORF
1 stop17h 02mMultiple Airlines
Deal found 1/21$264
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Fri 2/73:49 pmORF - ORD
1 stop8h 44mFrontier
Mon 2/247:08 pmORD - ORF
1 stop21h 26mFrontier
Deal found 1/20$266
This Southwest deal was found by Cheapflights users on 1/20. 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.
Wed 2/267:15 amORF - MDW
Nonstop2h 20mSouthwest
Sun 3/28:15 pmMDW - ORF
Nonstop2h 00mSouthwest
Deal found 1/20$306
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/124:42 pmORF - ORD
Nonstop2h 41mUnited Airlines
Sat 2/154:10 pmORD - ORF
1 stop6h 26mUnited Airlines
Deal found 1/20$315
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/107:00 amORF - MDW
1 stop8h 15mDelta
Fri 3/1412:51 pmMDW - ORF
1 stop4h 06mDelta
Deal found 1/21$326
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/35:39 amORF - ORD
1 stop6h 12mAmerican Airlines
Sun 4/63:54 pmORD - ORF
1 stop5h 44mAmerican Airlines
Deal found 1/21$326
This Southwest deal was found by Cheapflights users on 1/19. 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 2/266:35 amORF - ORD
2 stops11h 10mSouthwest
Thu 2/277:00 amORD - ORF
2 stops11h 25mSouthwest
Deal found 1/19$351
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/47:01 amORF - ORD
1 stop7h 12mDelta
Sun 4/66:15 pmORD - ORF
1 stop3h 50mDelta
Deal found 1/21$395
This Mytrip deal was found by Cheapflights users on 1/21. 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.
Tue 5/207:49 pmORF - RFD
1 stop15h 07mMultiple Airlines
Sat 5/2410:14 amRFD - ORF
2 stops21h 31mMultiple Airlines
Deal found 1/21$406
This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/194:52 pmORF - MDW
1 stop7h 47mFrontier
Sat 5/249:12 pmMDW - ORF
1 stop11h 01mFrontier
Deal found 1/20$470

Find flights from Virginia Beach to Chicago within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 4/22

5:28 am-3:57 pm

1 stop11h 29m

Chicago O'Hare Intl

Sat 4/26

4:30 pm-10:32 am

1 stop17h 02m

$264

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 2/10

3:46 pm-10:27 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 2/17

4:58 pm-5:34 pm

1 stop23h 36m

$266

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 2/18

6:00 am-7:37 am

Nonstop2h 37m

Chicago O'Hare Intl

Sat 2/22

6:06 am-11:18 am

1 stop4h 12m

$267

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 2/1

4:31 pm-9:34 am

2 stops18h 03m

Chicago O'Hare Intl

Sat 2/8

5:11 am-3:36 pm

1 stop9h 25m

$272

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 2/18

2:40 pm-9:30 pm

1 stop7h 50m

Chicago O'Hare Intl

Sat 2/22

4:20 pm-10:40 pm

1 stop5h 20m

$277

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 2/26

7:15 am-8:35 am

Nonstop2h 20m

Chicago Midway

Sun 3/2

8:15 pm-11:15 pm

Nonstop2h 00m

$306

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 5/20

6:00 am-11:48 am

1 stop6h 48m

Chicago O'Hare Intl

Sat 5/24

11:10 am-2:29 pm

Nonstop2h 19m

$316

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 3/10

7:00 am-2:15 pm

1 stop8h 15m

Chicago Midway

Fri 3/14

12:51 pm-5:57 pm

1 stop4h 06m

$326

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 4/4

7:01 am-1:13 pm

1 stop7h 12m

Chicago O'Hare Intl

Sun 4/6

6:15 pm-11:05 pm

1 stop3h 50m

$395

NorfolkChicago

ORF - RFD

ORFRFD

Norfolk

Tue 5/20

7:49 pm-9:56 am

1 stop15h 07m

Chicago Greater Rockford

Sat 5/24

10:14 am-8:45 am

2 stops21h 31m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 24 results
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2
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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.

Travel insights for flights from Virginia Beach to Chicago

Get recent, data-driven insights about flights from Virginia Beach to Chicago including ideal travel times, pricing trends, and more.

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 January 17, 2025.

Booking 36 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 $320). 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 January 21, 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 December 16, 2024.

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. Sunday 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 January 21, 2025.

The most flights from V1B to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 January 21, 2025.
Read reviews from past customers who have flown American Airlines, Spirit Airlines and United Airlines from Virginia Beach to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,985 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

  • 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 $55. Spirit Airlines flights start at $95 while deals on Southwest start at $119 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 Avianca (87%), ANA (84%) and Royal Jordanian (80%).

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

    The cheapest flight price from Virginia Beach to Chicago is $168. On average you can expect to pay $1,032. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $160.

  • 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 $320). 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 Virginia Beach?

Book flights to Virginia Beach if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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.
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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$226FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$390FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$189Average$396FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$250Average$368FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$268Average$388FlexibilityNo cancel feeOn-time63%
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