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 (29 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 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 $165. On average you can expect to pay $961. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $265.

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 (79%), Qatar Airways (78%) and Japan Airlines (78%).

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

Consider United Airlines, American 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

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 January or February, 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	$366

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

Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in October 2026

Search Deals

Cheapflights Insights

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 afternoon. If you’re flexible enough to do this you can expect to save up to 7% 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 evenings 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

4,215 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

4,215 reviews

Southwest

7.9

Good

4,215 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

7.4

Good

10,282 reviews

Southwest

7.9

Good

4,215 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

12,129 reviews

Southwest

7.9

Good

4,215 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

5.6

Fair

2,563 reviews

Southwest

7.9

Good

4,215 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 (79%), Qatar Airways (78%) and Japan Airlines (78%).
What are the cheapest flights from Virginia Beach to Chicago?
The cheapest flight price from Virginia Beach to Chicago is $165. On average you can expect to pay $961. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $265.
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.

See more FAQs

Benton Harbor

Lansing

Merrillville

Valparaiso

Hammond

Saint Joseph

Porter

Browse thousands of different options on Cheapflights for your next trip

Alternative routes

Chicago flight routes

Complete your trip

Flights by cabin class

Other flight options

Popular flights

Top destinations

Alternative routes for Virginia Beach to Chicago

Dulles Intl to O'Hare Intl flights

Reagan-National to O'Hare Intl flights

Dulles Intl to Midway flights

Raleigh to O'Hare Intl flights

Reagan-National to Midway flights

Raleigh to Midway flights

Norfolk to O'Hare Intl flights

Richmond to O'Hare Intl flights

Dulles Intl to St. Louis flights

Raleigh to St. Louis flights

Reagan-National to St. Louis flights

Greensboro to O'Hare Intl flights

Roanoke to O'Hare Intl flights

Richmond to Midway flights

Norfolk to Midway flights

Richmond to St. Louis flights

Greensboro to Midway flights

Charlottesville to O'Hare Intl flights

Lynchburg to O'Hare Intl flights

Greensboro to St. Louis flights

Raleigh to Peoria flights

Dulles Intl to Moline flights

Norfolk to St. Louis flights

Blountville to O'Hare Intl flights

Raleigh to Rockford flights

Charlottesville to Midway flights

Dulles Intl to Peoria flights

Reagan-National to Peoria flights

Raleigh to Moline flights

Richmond to Rockford flights

Greensboro to Peoria flights

Lynchburg to St. Louis flights

Norfolk to Moline flights

Raleigh to Bloomington flights

Charlottesville to St. Louis flights

Reagan-National to Evansville flights

Roanoke to St. Louis flights

Dulles Intl to Paducah flights

Dulles Intl to Champaign flights

Reagan-National to Paducah flights

Top 6 airlines flying from Virginia Beach to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$154	Average$369	FlexibilityNo cancel fee	On-time62%
JetBlue	Cheapest$220	Average$352	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$252	Average$393	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$260	Average$260	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$275	Average$462	FlexibilityNo cancel fee	On-time69%
Southwest	Cheapest$290	Average$418	FlexibilityNo cancel fee	On-time63%

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.

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

Most trusted provider

Popular in

Cheapest in

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 afternoon. If you’re flexible enough to do this you can expect to save up to 7% 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 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 Friday (29 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 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?

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.

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 3, 2026.

Complete your trip

Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Virginia Beach to Chicago by cabin class

Find flights from Virginia Beach to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Virginia Beach and Chicago flights

Browse other Virginia Beach and Chicago flight options. Last updated on October 3, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

Virginia Beach to Chicago flights

Consider these flights traveling from Virginia Beach to Chicago.

Top 6 airlines flying from Virginia Beach to Chicago

100% Free

Book with Flexibility

Travel Smart