How long is the flight from Virginia Beach to Chicago?

Departing from Virginia Beach to Chicago will take you 2h 15m. 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 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 $72. American Airlines flights start at $98 while deals on Southwest start at $119 one-way.

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.

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).

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 cheapest flights from Virginia Beach to Chicago?

The cheapest flight price from Virginia Beach to Chicago is $154. On average you can expect to pay $1,129. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $131.

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 (80%), Avianca (75%) and GoJet (74%).

What are the most popular airlines that fly from Virginia Beach to Chicago?

Consider American Airlines, United Airlines or Southwest when booking your flight. These represent the most popular airlines when flying from Virginia Beach to Chicago.

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.

$56+ Flights from Virginia Beach to Chicago

Q: How much does it cost to fly round-trip from Virginia Beach to Chicago?

Airfare is below average for this route at the moment. Virginia Beach to Chicago flights typically cost between $309 and $488 in January. The cheapest round-trip price found within the last 3 days was $255 on Delta (Jan 1-Jan 20).

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Virginia Beach to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 Saturday and return on a Tuesday

Cheap 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 18, 2025.

Mon 12/222:04 pmORF - ORD

1 stop5h 29mMultiple Airlines

Mon 1/55:00 amORD - ORF

1 stop8h 06mMultiple Airlines

Deal found 12/17

$313

Wed 12/3112:54 pmORF - ORD

Nonstop2h 28mAmerican Airlines

Mon 1/59:05 amORD - ORF

Nonstop2h 17mAmerican Airlines

Deal found 12/16

$331

Wed 12/3111:44 amORF - MDW

1 stop11h 28mFrontier

Mon 1/56:12 amMDW - ORF

1 stop5h 57mFrontier

Deal found 12/17

$343

Wed 12/3111:44 amORF - ORD

1 stop11h 40mFrontier

Mon 1/56:00 amORD - ORF

1 stop6h 09mFrontier

Deal found 12/17

$343

Wed 12/2411:44 amORF - MDW

1 stop11h 28mFrontier

Fri 12/266:12 amMDW - ORF

1 stop6h 27mFrontier

Deal found 12/16

$353

Mon 12/222:04 pmORF - MDW

1 stop9h 08mFrontier

Mon 1/56:12 amMDW - ORF

1 stop5h 57mFrontier

Deal found 12/17

$364

Fri 12/262:34 pmORF - ORD

1 stop8h 50mMultiple Airlines

Wed 1/74:49 pmORD - ORF

2 stops24h 49mMultiple Airlines

Deal found 12/17

$373

Fri 12/262:34 pmORF - ORD

1 stop8h 50mFrontier

Sat 1/36:10 amORD - ORF

1 stop9h 17mFrontier

Deal found 12/17

$377

Tue 12/237:40 pmORF - RFD

1 stop14h 18mMultiple Airlines

Tue 12/307:54 pmRFD - ORF

2 stops17h 12mMultiple Airlines

Deal found 12/16

$405

Fri 12/262:34 pmORF - ORD

1 stop8h 50mMultiple Airlines

Wed 12/315:00 amORD - ORF

1 stop8h 06mMultiple Airlines

Deal found 12/16

$409

Fri 12/262:34 pmORF - MDW

1 stop8h 38mFrontier

Sat 1/36:12 amMDW - ORF

1 stop9h 15mFrontier

Deal found 12/17

$410

Tue 12/237:40 pmORF - ORD

1 stop24h 22mSpirit Airlines

Tue 12/3012:09 pmORD - ORF

2 stops24h 57mSpirit Airlines

Deal found 12/16

$411

Best flights from Virginia Beach to Chicago
Discover carefully curated flight deals from Virginia Beach to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

Thu 1/15:23 amORF - MDW

1 stop4h 42mDelta

Tue 1/209:50 amMDW - ORF

1 stop6h 44mDelta

Deal found 12/17

$255

Tue 1/205:35 pmORF - MDW

Nonstop2h 15mSouthwest

Sat 1/3112:15 pmMDW - ORF

1 stop4h 35mSouthwest

Deal found 12/16

$259

Sat 4/1110:23 amORF - MDW

1 stop12h 35mFrontier

Sun 4/123:10 pmMDW - ORF

1 stop17h 13mFrontier

Deal found 12/17

$268

Tue 1/66:30 amORF - ORD

1 stop6h 35mUnited Airlines

Tue 1/64:15 pmORD - ORF

1 stop6h 12mUnited Airlines

Deal found 12/15

$283

Thu 1/226:45 amORF - ORD

3 stops18h 01mSpirit Airlines

Thu 1/295:15 amORD - ORF

3 stops15h 35mSpirit Airlines

Deal found 12/15

$285

Fri 2/1311:32 amORF - MDW

1 stop7h 21mMultiple Airlines

Sun 2/157:30 amMDW - ORF

1 stop13h 20mMultiple Airlines

Deal found 12/17

$311

Mon 2/91:38 pmORF - ORD

1 stop8h 08mAmerican Airlines

Wed 2/115:05 pmORD - ORF

1 stop4h 53mAmerican Airlines

Deal found 12/17

$313

Sat 1/1711:15 amORF - MDW

2 stops8h 25mSouthwest

Sun 1/189:50 amMDW - ORF

1 stop7h 00mSouthwest

Deal found 12/18

$266

Tue 1/205:35 amORF - MDW

1 stop4h 17mDelta

Sat 1/3110:46 amMDW - ORF

1 stop5h 25mDelta

Deal found 12/16

$269

Thu 2/264:55 pmORF - ORD

Nonstop2h 35mUnited Airlines

Tue 3/36:02 pmORD - ORF

Nonstop2h 09mUnited Airlines

Deal found 12/15

$293

Tue 1/65:35 amORF - MDW

1 stop4h 17mDelta

Sun 1/185:59 pmMDW - ORF

1 stop5h 17mDelta

Deal found 12/16

$269

Fri 3/63:26 pmORF - MDW

1 stop6h 27mFrontier

Mon 3/96:15 amMDW - ORF

1 stop7h 16mFrontier

Deal found 12/17

$301

Sun 1/185:35 pmORF - MDW

Nonstop2h 15mSouthwest

Fri 1/305:30 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 12/16

$290

Tue 1/65:35 amORF - MDW

1 stop4h 17mDelta

Sat 1/175:31 pmMDW - ORF

1 stop5h 45mDelta

Deal found 12/16

$269

Wed 1/2110:05 amORF - ORD

Nonstop2h 35mUnited Airlines

Thu 1/2212:00 pmORD - ORF

1 stop6h 00mUnited Airlines

Deal found 12/16

$303

Mon 1/125:35 pmORF - MDW

Nonstop2h 15mSouthwest

Wed 1/145:30 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 12/16

$308

Tue 1/64:45 pmORF - ORD

Nonstop2h 34mUnited Airlines

Thu 1/87:10 amORD - ORF

1 stop7h 17mUnited Airlines

Deal found 12/16

$318

Tue 1/610:05 amORF - ORD

Nonstop2h 35mUnited Airlines

Sat 1/171:55 pmORD - ORF

Nonstop2h 11mUnited Airlines

Deal found 12/16

$319

Mon 4/276:00 amORF - ORD

Nonstop2h 30mUnited Airlines

Wed 4/2911:00 amORD - ORF

Nonstop2h 19mUnited Airlines

Deal found 12/17

$323

Thu 1/224:45 pmORF - ORD

Nonstop2h 34mUnited Airlines

Mon 1/2611:05 amORD - ORF

Nonstop2h 20mUnited Airlines

Deal found 12/17

$323

Mon 4/205:00 pmORF - ORD

Nonstop2h 30mUnited Airlines

Wed 4/225:50 pmORD - ORF

Nonstop2h 19mUnited Airlines

Deal found 12/17

$323

Thu 1/2210:05 amORF - ORD

Nonstop2h 35mUnited Airlines

Thu 1/2911:05 amORD - ORF

Nonstop2h 20mUnited Airlines

Deal found 12/15

$323

Thu 1/224:45 pmORF - ORD

Nonstop2h 34mUnited Airlines

Mon 2/26:10 pmORD - ORF

Nonstop2h 22mUnited Airlines

Deal found 12/15

$323

Last-minute flights from Virginia Beach to Chicago
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated December 18, 2025 and is based on user searches.

Thu 1/15:23 amORF - MDW

1 stop4h 42mDelta

Tue 1/209:50 amMDW - ORF

1 stop6h 44mDelta

Deal found 12/17

$255

Thu 1/18:15 amORF - ORD

1 stop4h 44mAmerican Airlines

Tue 1/2010:10 amORD - ORF

1 stop5h 00mAmerican Airlines

Deal found 12/17

$255

Mon 1/53:01 pmORF - ORD

1 stop10h 29mSpirit Airlines

Thu 1/155:15 amORD - ORF

1 stop12h 23mSpirit Airlines

Deal found 12/16

$267

Tue 1/63:01 pmORF - ORD

3 stops29h 01mSpirit Airlines

Thu 1/84:38 pmORD - ORF

3 stops25h 00mSpirit Airlines

Deal found 12/16

$259

Tue 1/65:35 amORF - MDW

1 stop4h 17mDelta

Sat 1/175:31 pmMDW - ORF

1 stop5h 45mDelta

Deal found 12/16

$269

Tue 1/65:35 amORF - MDW

1 stop4h 17mDelta

Wed 1/149:50 amMDW - ORF

1 stop6h 23mDelta

Deal found 12/16

$283

Wed 1/1410:05 amORF - ORD

Nonstop2h 35mUnited Airlines

Wed 1/218:45 amORD - ORF

1 stop4h 22mUnited Airlines

Deal found 12/17

$273

Sat 1/1711:15 amORF - MDW

2 stops8h 25mSouthwest

Sun 1/189:50 amMDW - ORF

1 stop7h 00mSouthwest

Deal found 12/18

$266

Mon 1/1911:17 amORF - MDW

1 stop12h 02mMultiple Airlines

Fri 1/301:00 pmMDW - ORF

1 stop7h 50mMultiple Airlines

Deal found 12/16

$270

Tue 1/205:35 pmORF - MDW

Nonstop2h 15mSouthwest

Sat 1/3112:15 pmMDW - ORF

1 stop4h 35mSouthwest

Deal found 12/16

$259

Sun 1/257:33 pmORF - ORD

3 stops28h 09mSpirit Airlines

Fri 1/303:22 pmORD - ORF

3 stops29h 28mSpirit Airlines

Deal found 12/16

$256

Wed 1/285:35 pmORF - MDW

Nonstop2h 15mSouthwest

Sat 1/316:00 amMDW - ORF

1 stop5h 55mSouthwest

Deal found 12/16

$273

One-way flights from Virginia Beach to Chicago
Search for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated December 18, 2025.

Wed 2/46:15 pmORF - ORD

1 stop6h 32mSpirit Airlines

Deal found 12/18

$56

Wed 2/187:31 pmORF - ORD

1 stop28h 53mMultiple Airlines

Deal found 12/17

$64

Thu 1/87:33 pmORF - ORD

1 stop16h 49mSpirit Airlines

Deal found 12/18

$65

Sat 2/79:10 pmORF - MDW

1 stop23h 42mFrontier

Deal found 12/18

$70

Sat 2/79:10 pmORF - ORD

1 stop13h 00mFrontier

Deal found 12/18

$70

Fri 1/167:33 pmORF - ORD

1 stop16h 49mSpirit Airlines

Deal found 12/17

$72

Sat 1/246:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Deal found 12/18

$74

Mon 1/197:33 pmORF - ORD

1 stop16h 49mSpirit Airlines

Deal found 12/16

$77

Thu 1/156:45 amORF - MDW

1 stop27h 24mMultiple Airlines

Deal found 12/17

$80

Thu 1/156:45 amORF - ORD

1 stop13h 56mMultiple Airlines

Deal found 12/17

$80

Thu 4/912:03 pmORF - ORD

1 stop6h 09mFrontier

Deal found 12/18

$81

Mon 1/267:33 pmORF - ORD

2 stops18h 40mSpirit Airlines

Deal found 12/18

$83

Find flight deals from Virginia Beach to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$255 (Delta)
One-way from	$56 (Priceline)
Popular in	December
Cheapest in	September
Average price	$390

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. 2% potential increase in price ($10 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 December 2025

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from Virginia Beach to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 1/1

5:23 am-9:05 am

1 stop4h 42m

Chicago Midway

Tue 1/20

9:50 am-5:34 pm

1 stop6h 44m

$255

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 1/20

5:35 pm-6:50 pm

Nonstop2h 15m

Chicago Midway

Sat 1/31

12:15 pm-5:50 pm

1 stop4h 35m

$259

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 1/17

11:15 am-6:40 pm

2 stops8h 25m

Chicago Midway

Sun 1/18

9:50 am-5:50 pm

1 stop7h 00m

$266

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 4/11

10:23 am-9:58 pm

1 stop12h 35m

Chicago Midway

Sun 4/12

3:10 pm-9:23 am

1 stop17h 13m

$268

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 1/20

5:35 am-8:52 am

1 stop4h 17m

Chicago Midway

Sat 1/31

10:46 am-5:11 pm

1 stop5h 25m

$269

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 1/6

5:35 am-8:52 am

1 stop4h 17m

Chicago Midway

Sun 1/18

5:59 pm-12:16 am

1 stop5h 17m

$269

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 1/6

5:35 am-8:52 am

1 stop4h 17m

Chicago Midway

Sat 1/17

5:31 pm-12:16 am

1 stop5h 45m

$269

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 1/6

6:30 am-12:05 pm

1 stop6h 35m

Chicago O'Hare Intl

Tue 1/6

4:15 pm-11:27 pm

1 stop6h 12m

$283

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 1/22

6:45 am-11:46 pm

3 stops18h 01m

Chicago O'Hare Intl

Thu 1/29

5:15 am-9:50 pm

3 stops15h 35m

$285

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sun 1/18

5:35 pm-6:50 pm

Nonstop2h 15m

Chicago Midway

Fri 1/30

5:30 pm-8:30 pm

Nonstop2h 00m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 47 results

...

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?

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?

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 16% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Virginia Beach to Chicago?

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.

How much does it cost to fly round-trip from Virginia Beach to Chicago?

Reviews of airlines servicing Chicago

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

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Southwest

7.9

Good

4,250 reviews

Southwest

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

United Airlines

7.4

Good

9,091 reviews

Southwest

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

American Airlines

7.2

Good

11,054 reviews

Southwest

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Spirit Airlines

6.3

Okay

8,190 reviews

Southwest

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Frontier

5.8

Fair

3,081 reviews

Southwest

7.9

Good

4,250 reviews

Reviews

1 / 20

2.0

Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

How long is the flight from Virginia Beach to Chicago?
Departing from Virginia Beach to Chicago will take you 2h 15m. 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 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 $72. American Airlines flights start at $98 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 ANA (80%), Avianca (75%) and GoJet (74%).
What are the cheapest flights from Virginia Beach to Chicago?
The cheapest flight price from Virginia Beach to Chicago is $154. On average you can expect to pay $1,129. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $131.
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

Lansing

Merrillville

Hammond

Porter

Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Top 6 airlines flying from Virginia Beach to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$65	Average$249	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$108	Average$260	FlexibilityNo cancel fee	On-timeN/A
Frontier	Cheapest$176	Average$208	FlexibilityNo cancel fee	On-time62%
Southwest	Cheapest$181	Average$364	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$214	Average$385	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$217	Average$362	FlexibilityNo cancel fee	On-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$56+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Virginia Beach to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 Saturday and return on a Tuesday

Cheap flight deals from Virginia Beach to Chicago

Cheapest flights from Virginia Beach to ChicagoExplore 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 18, 2025.

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 18, 2025.

Find 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 December 18, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Virginia Beach to Chicago that are best for you.

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.

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 December 12, 2025.

What is the cheapest month to book a flight from Virginia Beach to Chicago?

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 18, 2025.

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 13, 2025.

How much does it cost to fly round-trip from Virginia Beach to Chicago?

Reviews of airlines servicing Chicago

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.

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?

What are the cheapest airlines to fly from Virginia Beach to Chicago one-way?

What are the most popular routes from Virginia Beach to Chicago?

What are the most reliable airlines from Virginia Beach to Chicago?

What are the cheapest flights from Virginia Beach to Chicago?

Can I find deals for flights from Virginia Beach to Chicago that include hotel bookings?

How can I find direct flights from Virginia Beach to Chicago?

Can I find deals for business class flights from Virginia Beach to Chicago?

What is the cheapest month to book a flight from Virginia Beach to Chicago?

Traveling to a place near Chicago?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Virginia Beach to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Virginia Beach to Chicago

100% Free

Book with Flexibility

Travel Smart

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 18, 2025.