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 $80 while deals on Southwest start at $132 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 $134. On average you can expect to pay $1,038. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $112.

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

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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 Friday 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 29, 2025.

Tue 12/303:11 pmORF - ORD

1 stop20h 07mFrontier

Tue 1/62:26 pmORD - ORF

1 stop19h 19mFrontier

Deal found 12/27

$546

Tue 12/303:11 pmORF - MDW

1 stop7h 47mFrontier

Tue 1/66:52 amMDW - ORF

1 stop26h 53mFrontier

Deal found 12/27

$554

Tue 12/303:01 pmORF - ORD

2 stops18h 30mSpirit Airlines

Tue 1/64:38 pmORD - ORF

2 stops20h 28mSpirit Airlines

Deal found 12/27

$569

Mon 12/293:01 pmORF - ORD

1 stop10h 29mSpirit Airlines

Mon 1/512:09 pmORD - ORF

1 stop5h 36mSpirit Airlines

Deal found 12/27

$605

Mon 12/292:04 pmORF - ORD

2 stops24h 36mMultiple Airlines

Mon 1/59:47 amORD - ORF

1 stop7h 58mMultiple Airlines

Deal found 12/27

$623

Wed 12/315:46 pmORF - ORD

1 stop7h 10mMultiple Airlines

Fri 1/210:12 amORD - ORF

1 stop24h 58mMultiple Airlines

Deal found 12/28

$624

Tue 12/305:33 pmORF - ORD

1 stop7h 23mMultiple Airlines

Mon 1/512:25 pmORD - ORF

1 stop24h 02mMultiple Airlines

Deal found 12/29

$629

Tue 12/303:11 pmORF - MDW

1 stop7h 47mMultiple Airlines

Mon 1/53:10 pmMDW - ORF

1 stop26h 35mMultiple Airlines

Deal found 12/29

$646

Mon 12/292:04 pmORF - MDW

1 stop9h 08mMultiple Airlines

Mon 1/53:10 pmMDW - ORF

1 stop26h 35mMultiple Airlines

Deal found 12/27

$671

Mon 12/292:04 pmORF - MDW

1 stop9h 08mMultiple Airlines

Sun 1/42:16 pmMDW - ORF

1 stop27h 29mMultiple Airlines

Deal found 12/28

$681

Mon 12/293:01 pmORF - ORD

1 stop10h 29mSpirit Airlines

Wed 12/315:00 amORD - ORF

1 stop8h 06mSpirit Airlines

Deal found 12/27

$693

Tue 12/305:33 pmORF - ORD

1 stop7h 23mMultiple Airlines

Sun 1/41:15 pmORD - ORF

2 stops22h 54mMultiple Airlines

Deal found 12/29

$696

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 29, 2025.

Wed 2/46:15 pmORF - ORD

1 stop6h 32mSpirit Airlines

Mon 2/95:15 amORD - ORF

1 stop12h 23mSpirit Airlines

Deal found 12/27

$112

Wed 2/46:15 pmORF - ORD

1 stop29h 21mMultiple Airlines

Mon 2/94:19 pmORD - ORF

2 stops18h 46mMultiple Airlines

Deal found 12/27

$158

Sat 2/77:32 amORF - ORD

Nonstop2h 38mAmerican Airlines

Sat 2/77:25 pmORD - ORF

Nonstop2h 07mAmerican Airlines

Deal found 12/28

$263

Fri 1/236:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Mon 1/265:15 amORD - ORF

1 stop12h 23mSpirit Airlines

Deal found 12/28

$135

Sat 2/216:20 amORF - ORD

1 stop4h 14mUnited Airlines

Tue 2/2411:05 amORD - ORF

Nonstop2h 17mUnited Airlines

Deal found 12/26

$273

Sat 2/75:20 amORF - MDW

1 stop5h 33mDelta

Sat 2/74:30 pmMDW - ORF

1 stop6h 46mDelta

Deal found 12/28

$283

Wed 1/285:35 pmORF - MDW

Nonstop2h 15mSouthwest

Mon 3/26:10 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 12/29

$293

Fri 2/276:45 amORF - ORD

2 stops17h 39mMultiple Airlines

Mon 3/27:00 amORD - ORF

1 stop10h 26mMultiple Airlines

Deal found 12/28

$162

Fri 1/306:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Sun 2/15:15 amORD - ORF

1 stop12h 23mSpirit Airlines

Deal found 12/27

$158

Fri 1/237:33 pmORF - ORD

1 stop16h 49mMultiple Airlines

Mon 1/268:45 amORD - ORF

2 stops27h 46mMultiple Airlines

Deal found 12/28

$182

Fri 1/237:33 pmORF - ORD

1 stop16h 49mSpirit Airlines

Tue 1/275:32 pmORD - ORF

2 stops23h 53mSpirit Airlines

Deal found 12/28

$178

Wed 1/2810:31 pmORF - MDW

2 stops46h 21mMultiple Airlines

Mon 3/29:22 pmMDW - ORF

1 stop13h 43mMultiple Airlines

Deal found 12/29

$206

Sat 2/710:05 amORF - ORD

Nonstop2h 35mUnited Airlines

Sat 2/76:17 pmORD - ORF

1 stop4h 13mUnited Airlines

Deal found 12/28

$273

Mon 1/127:33 pmORF - ORD

2 stops23h 52mMultiple Airlines

Fri 1/165:15 amORD - ORF

1 stop12h 23mMultiple Airlines

Deal found 12/28

$206

Sat 1/245:20 amORF - MDW

1 stop5h 33mDelta

Sat 1/314:30 pmMDW - ORF

1 stop6h 46mDelta

Deal found 12/27

$283

Sat 1/246:10 amORF - MDW

2 stops8h 30mSouthwest

Sat 1/3112:15 pmMDW - ORF

1 stop4h 35mSouthwest

Deal found 12/26

$298

Wed 2/111:01 pmORF - MDW

1 stop5h 54mDelta

Wed 2/1812:45 pmMDW - ORF

1 stop6h 43mDelta

Deal found 12/28

$289

Sat 2/76:10 amORF - MDW

1 stop6h 15mSouthwest

Sat 2/712:45 pmMDW - ORF

2 stops7h 50mSouthwest

Deal found 12/28

$309

Fri 2/133:18 pmORF - ORD

2 stops21h 04mMultiple Airlines

Sun 2/152:13 pmORD - ORF

1 stop7h 13mMultiple Airlines

Deal found 12/27

$235

Mon 3/169:50 amORF - MDW

2 stops9h 00mSouthwest

Wed 3/186:05 pmMDW - ORF

Nonstop2h 00mSouthwest

Deal found 12/27

$312

Wed 3/117:00 amORF - MDW

1 stop7h 25mDelta

Sat 3/149:35 amMDW - ORF

1 stop5h 44mDelta

Deal found 12/27

$315

Sat 1/246:45 amORF - MDW

2 stops30h 00mMultiple Airlines

Sat 1/319:38 amMDW - ORF

1 stop24h 10mMultiple Airlines

Deal found 12/27

$294

Last-minute flights from Virginia Beach to Chicago
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated December 29, 2025 and is based on user searches.

Sun 1/117:33 pmORF - ORD

1 stop16h 49mMultiple Airlines

Thu 1/151:13 pmORD - ORF

1 stop28h 25mMultiple Airlines

Deal found 12/26

$188

Sun 1/112:29 pmORF - MDW

1 stop9h 30mMultiple Airlines

Thu 1/1511:27 amMDW - ORF

1 stop9h 23mMultiple Airlines

Deal found 12/29

$280

Sat 1/176:45 amORF - ORD

1 stop8h 54mMultiple Airlines

Tue 1/205:32 pmORD - ORF

2 stops23h 53mMultiple Airlines

Deal found 12/27

$157

Fri 1/236:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Mon 1/265:15 amORD - ORF

1 stop12h 23mSpirit Airlines

Deal found 12/28

$135

Fri 1/237:33 pmORF - ORD

1 stop16h 49mMultiple Airlines

Tue 1/275:53 pmORD - ORF

2 stops44h 13mMultiple Airlines

Deal found 12/28

$173

Fri 1/237:33 pmORF - ORD

1 stop16h 49mSpirit Airlines

Tue 1/275:32 pmORD - ORF

2 stops23h 53mSpirit Airlines

Deal found 12/28

$178

Fri 1/237:33 pmORF - ORD

1 stop16h 49mMultiple Airlines

Mon 1/268:45 amORD - ORF

2 stops27h 46mMultiple Airlines

Deal found 12/28

$182

Sat 1/246:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Sat 1/3110:48 amORD - ORF

1 stop10h 02mSpirit Airlines

Deal found 12/27

$165

Mon 1/266:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Tue 2/35:15 amORD - ORF

1 stop12h 23mSpirit Airlines

Deal found 12/27

$125

Wed 1/2810:31 pmORF - MDW

2 stops46h 21mMultiple Airlines

Mon 3/29:22 pmMDW - ORF

1 stop13h 43mMultiple Airlines

Deal found 12/29

$206

Fri 1/306:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Mon 2/25:15 amORD - ORF

1 stop12h 23mSpirit Airlines

Deal found 12/28

$146

Fri 1/306:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Sun 2/15:15 amORD - ORF

1 stop12h 23mSpirit Airlines

Deal found 12/29

$158

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 29, 2025.

Wed 2/46:15 pmORF - ORD

1 stop6h 32mSpirit Airlines

Deal found 12/29

$56

Fri 1/307:33 pmORF - ORD

1 stop25h 11mMultiple Airlines

Deal found 12/28

$64

Thu 1/227:33 pmORF - ORD

1 stop16h 49mSpirit Airlines

Deal found 12/29

$65

Thu 2/54:01 pmORF - MDW

1 stop28h 51mFrontier

Deal found 12/29

$68

Sat 1/316:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Deal found 12/27

$68

Thu 1/296:45 amORF - ORD

1 stop12h 07mSpirit Airlines

Deal found 12/28

$70

Sat 2/216:45 amORF - ORD

1 stop12h 01mSpirit Airlines

Deal found 12/29

$72

Thu 2/196:45 amORF - MDW

1 stop8h 41mMultiple Airlines

Deal found 12/29

$73

Fri 1/306:45 amORF - MDW

1 stop14h 07mMultiple Airlines

Deal found 12/29

$74

Fri 2/66:45 amORF - MDW

1 stop14h 07mMultiple Airlines

Deal found 12/28

$75

Fri 1/236:45 amORF - MDW

1 stop14h 07mMultiple Airlines

Deal found 12/29

$76

Sat 2/76:45 amORF - ORD

1 stop10h 55mMultiple Airlines

Deal found 12/26

$76

Find flight deals from Virginia Beach to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$112 (Super.com)
One-way from	$56 (Expedia)
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 - ORD

ORFORD

Norfolk

Wed 2/4

6:15 pm-11:47 pm

1 stop6h 32m

Chicago O'Hare Intl

Mon 2/9

5:15 am-6:38 pm

1 stop12h 23m

$112

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 1/23

6:45 am-5:52 pm

1 stop12h 07m

Chicago O'Hare Intl

Mon 1/26

5:15 am-6:38 pm

1 stop12h 23m

$135

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 2/4

6:15 pm-10:36 pm

1 stop29h 21m

Chicago O'Hare Intl

Mon 2/9

4:19 pm-12:05 pm

2 stops18h 46m

$158

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 1/30

6:45 am-5:52 pm

1 stop12h 07m

Chicago O'Hare Intl

Sun 2/1

5:15 am-6:38 pm

1 stop12h 23m

$158

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 2/27

6:45 am-11:24 pm

2 stops17h 39m

Chicago O'Hare Intl

Mon 3/2

7:00 am-6:26 pm

1 stop10h 26m

$162

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 1/23

7:33 pm-11:22 am

1 stop16h 49m

Chicago O'Hare Intl

Tue 1/27

5:32 pm-6:25 pm

2 stops23h 53m

$178

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 1/23

7:33 pm-11:22 am

1 stop16h 49m

Chicago O'Hare Intl

Mon 1/26

8:45 am-1:31 pm

2 stops27h 46m

$182

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 1/28

10:31 pm-7:52 pm

2 stops46h 21m

Chicago Midway

Mon 3/2

9:22 pm-12:05 pm

1 stop13h 43m

$206

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 1/12

7:33 pm-6:25 pm

2 stops23h 52m

Chicago O'Hare Intl

Fri 1/16

5:15 am-6:38 pm

1 stop12h 23m

$206

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 2/13

3:18 pm-11:22 am

2 stops21h 04m

Chicago O'Hare Intl

Sun 2/15

2:13 pm-10:26 pm

1 stop7h 13m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 43 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 12% 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 at noon 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.

Weekly flight availability from Virginia Beach to Chicago

The most flights from V1B to CHI are scheduled on a Monday (23 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (17 on average).

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

8.0

Very good

4,252 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

8.0

Very good

4,252 reviews

Southwest

8.0

Very good

4,252 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

9,120 reviews

Southwest

8.0

Very good

4,252 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

11,072 reviews

Southwest

8.0

Very good

4,252 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

8,221 reviews

Southwest

8.0

Very good

4,252 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

5.7

Fair

3,063 reviews

Southwest

8.0

Very good

4,252 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 $80 while deals on Southwest start at $132 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 $134. On average you can expect to pay $1,038. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $112.
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$367	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$215	Average$385	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$215	Average$364	FlexibilityNo cancel fee	On-time71%

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$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

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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 Friday 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 29, 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 29, 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 29, 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 26, 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 29, 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 27, 2025.

Weekly flight availability 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?

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Alternative routes for Virginia Beach to Chicago

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Top 6 airlines flying from Virginia Beach to Chicago

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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 29, 2025.