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 $69. United Airlines flights start at $132 while deals on Southwest start at $137 one-way.

Weekly flight availability from Virginia Beach to Chicago

The most flights from V1B to CHI are scheduled on a Friday (38 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (29 on average).

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 $198. On average you can expect to pay $793. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $264.

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 (86%), Avianca (83%) and Air Canada (81%).

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.

Find Cheap Flights from Virginia Beach to Chicago

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Cheapflights Tip: The best prices from Virginia Beach to Chicago are usually found in January or August, booked 65 days in advance, depart on a Thursday or Wednesday and return on a Saturday

Find flight deals from Virginia Beach to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Popular in	July
Cheapest in	January
Average price	$378

Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.

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Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.

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Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).

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Average for round-trip flights in October 2026

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Everything you need to know about your flight from Virginia Beach to Chicago

Prices

Airlines

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 evening. If you’re flexible enough to do this you can expect to save up to 8% on your trip compared to booking a flight in the morning.

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 Friday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican 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

4,212 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Southwest

7.9

Good

4,212 reviews

Southwest

7.9

Good

4,212 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

United Airlines

7.3

Good

10,388 reviews

Southwest

7.9

Good

4,212 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

American Airlines

7.0

Good

12,178 reviews

Southwest

7.9

Good

4,212 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Frontier

5.5

Fair

2,527 reviews

Southwest

7.9

Good

4,212 reviews

Reviews

1 / 20

6.0

Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

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 $69. United Airlines flights start at $132 while deals on Southwest start at $137 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 (86%), Avianca (83%) and Air Canada (81%).
What are the cheapest flights from Virginia Beach to Chicago?
The cheapest flight price from Virginia Beach to Chicago is $198. On average you can expect to pay $793. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $264.
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.

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Top 6 airlines flying from Virginia Beach to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$176	Average$397	FlexibilityNo cancel fee	On-time62%
JetBlue	Cheapest$220	Average$352	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$253	Average$397	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$260	Average$260	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$275	Average$476	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$290	Average$419	FlexibilityNo cancel fee	On-time63%

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Cheap flights from Virginia Beach, VA to Chicago (CHI)

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

Find flight deals from Virginia Beach to Chicago

Most accurate provider

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Popular in

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Average price

Cheapflights Insights

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 evening. If you’re flexible enough to do this you can expect to save up to 8% on your trip compared to booking a flight in the morning.

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 Friday at noon when fares are most often at their lowest. Sunday mornings 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 Friday (38 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (29 on average).

Reviews of airlines servicing Chicago

Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican 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

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?

Traveling to a place near Chicago?

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Other flights to Chicago

Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 19, 2026.

Complete your trip

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