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$54+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Dec 24 — Dec 311
Tue 12/24
Tue 12/31
1 adult, Economy
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The best prices from Virginia Beach to Chicago are usually found in March or February, 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 December 19, 2024.

Round-trip from

$277
(American Airlines)

One-way from

$54
(Mytrip)

Popular in

June

Cheapest in

March

Average price

$384
From Virginia Beach to Chicago (CHI)
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One-way flight from Virginia Beach to Chicago (CHI)
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High demand for flights, 3% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in December 2024
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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 December 19, 2024.

This American Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/257:00 amORF - ORD
Nonstop2h 35mAmerican Airlines
Mon 12/306:55 pmORD - ORF
Nonstop2h 34mAmerican Airlines
Deal found 12/18$488
This Delta deal was found by Cheapflights users on 12/18. 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.
Sun 12/295:10 pmORF - ORD
1 stop6h 42mDelta
Tue 12/3110:30 amORD - ORF
1 stop6h 46mDelta
Deal found 12/18$496
This FlightHub deal was found by Cheapflights users on 12/18. 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.
Sun 12/223:26 pmORF - ORD
1 stop6h 43mMultiple Airlines
Sat 1/48:14 pmORD - ORF
1 stop11h 36mMultiple Airlines
Deal found 12/18$500
This Southwest deal was found by Cheapflights users on 12/18. 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.
Mon 12/307:45 pmORF - MDW
Nonstop2h 15mSouthwest
Fri 1/36:30 amMDW - ORF
1 stop7h 45mSouthwest
Deal found 12/18$514
This United Airlines deal was found by Cheapflights users on 12/18. 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.
Fri 12/276:15 amORF - ORD
Nonstop2h 30mUnited Airlines
Thu 1/27:15 amORD - ORF
Nonstop2h 23mUnited Airlines
Deal found 12/18$539
This Delta deal was found by Cheapflights users on 12/18. 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 12/236:36 amORF - MDW
1 stop5h 45mDelta
Tue 12/313:32 pmMDW - ORF
1 stop6h 18mDelta
Deal found 12/18$626
This Frontier deal was found by Cheapflights users on 12/18. 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.
Sun 12/223:26 pmORF - ORD
1 stop6h 43mFrontier
Sun 12/2911:24 amORD - ORF
1 stop7h 37mFrontier
Deal found 12/18$663
This FlightHub deal was found by Cheapflights users on 12/18. 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.
Sun 12/229:01 pmORF - MDW
1 stop21h 53mFrontier
Sat 1/46:49 pmMDW - ORF
1 stop24h 12mFrontier
Deal found 12/18$713
This CheapOair deal was found by Cheapflights users on 12/18. 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.
Mon 12/309:45 amORF - ORD
1 stop5h 51mSpirit Airlines
Fri 1/38:14 pmORD - ORF
1 stop11h 36mSpirit Airlines
Deal found 12/18$732
This Mytrip deal was found by Cheapflights users on 12/18. 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 12/279:26 pmORF - RFD
2 stops21h 59mMultiple Airlines
Thu 1/25:05 pmRFD - ORF
3 stops38h 45mMultiple Airlines
Deal found 12/18$796
This Southwest deal was found by Cheapflights users on 12/18. 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.
Fri 12/2010:05 amORF - ORD
1 stop4h 55mSouthwest
Tue 12/3111:25 amORD - ORF
2 stops9h 25mSouthwest
Deal found 12/18$811

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 December 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 1/16

6:30 am-8:01 am

Nonstop2h 31m

Chicago O'Hare Intl

Sat 1/18

6:54 pm-10:06 pm

Nonstop2h 12m

$277

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 1/9

5:25 am-4:10 pm

1 stop11h 45m

Chicago O'Hare Intl

Sun 1/12

11:12 am-11:59 pm

3 stops35h 47m

$283

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 1/9

5:25 am-11:20 am

1 stop6h 55m

Chicago O'Hare Intl

Sun 1/12

7:26 am-9:36 pm

1 stop13h 10m

$287

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 1/16

12:55 pm-6:14 pm

1 stop6h 19m

Chicago Midway

Sat 1/18

3:41 pm-9:21 pm

1 stop4h 40m

$296

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 1/16

2:40 pm-8:30 pm

2 stops6h 50m

Chicago Midway

Sat 1/18

5:55 am-2:10 pm

1 stop7h 15m

$301

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 1/16

11:25 am-4:13 pm

1 stop5h 48m

Chicago O'Hare Intl

Sun 1/19

7:30 am-2:47 pm

1 stop6h 17m

$311

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 1/10

6:37 am-8:07 am

Nonstop2h 30m

Chicago O'Hare Intl

Mon 1/13

7:10 am-2:35 pm

1 stop6h 25m

$317

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 1/31

6:35 am-4:45 pm

2 stops11h 10m

Chicago O'Hare Intl

Sun 2/2

7:00 am-3:35 pm

1 stop7h 35m

$331

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sun 12/22

3:26 pm-9:09 pm

1 stop6h 43m

Chicago O'Hare Intl

Sun 12/29

11:24 am-8:01 pm

1 stop7h 37m

$663

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 1/27

3:46 pm-10:27 pm

1 stop7h 41m

$54

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 21 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.

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 December 13, 2024.

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, September is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $232). Flying from Virginia Beach to Chicago in June is currently the most expensive (average of $308). 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 December 19, 2024.

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.

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 December 19, 2024.
Read reviews from past customers who have flown American Airlines, United Airlines and Delta 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
4,836 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

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
4,836 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

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
8,600 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

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
9,048 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

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
4,836 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

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.

Spirit Airlines
6.3
Okay
8,120 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

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 $54. Spirit Airlines flights start at $89 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 Envoy Air (96%), ANA (95%) and Avianca (90%).

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

    The cheapest flight price from Virginia Beach to Chicago is $185. On average you can expect to pay $906. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $138.

  • 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, September is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $232). Flying from Virginia Beach to Chicago in June is currently the most expensive (average of $308). 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

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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 December 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$387FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$189Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$248Average$364FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$268Average$391FlexibilityNo cancel feeOn-time63%
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