Cheap flights from Virginia Beach to Chicago (CHI)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from Virginia Beach to Chicago are usually found in February or January, booked 26 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

How to find the cheapest flight from
Virginia Beach to Chicago (CHI)

All the information you need to plan the best null to CHI flight in 2022: compare Virginia Beach to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
V1B - CHI
Price
$217 - $369
CHI
Temperature
23 - 73.4 °F
CHI
Rainfall
1.7 - 4.9 inches

Popular in

June

High demand for flights, 23% potential price rise

Cheapest in

February

Best time to find cheap flights, 24% potential price drop

Round-trip from

$217

From Virginia Beach to Chicago (CHI)

One-way from

$173

One-way flight from Virginia Beach to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
When is the cheapest time to fly from Virginia Beach to Chicago (V1B - CHI)?

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 month to fly from Virginia Beach to Chicago?

The best pricing can be found in the month of February. Prices to Chicago from Virginia Beach average $284. You can even find prices in February for less than $284, as users have found deals to Chicago from as low as $197. The month of June appears to be one of the more expensive times to travel to Chicago from Virginia Beach. Flying in the targeted month can save you up to 29%.

How far in advance should I book a flight from Virginia Beach to Chicago?

Travelers have found it’s best to book a flight 24 days in advance to save up to 31% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 24 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Virginia Beach to Chicago 1-2 weeks in advance for as low as $314, or $387 for flights within the next 24 hours.

Cheap flights from Virginia Beach to Chicago in August, September 2022

The best prices found for Virginia Beach to CHI flights for August, September
26 Aug - 29 Aug
$178pp
ORF
Norfolk
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
22 Aug - 26 Aug
$184pp
ORF
Norfolk
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk
24 Aug - 31 Aug
$185pp
ORF
Norfolk
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
ORF
Norfolk

Virginia Beach to Chicago 2022 flight deals

Cheap flights to Chicago from Virginia Beach found for this year
26 Aug - 31 Aug
$178pp
ORF
Norfolk
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
22 Aug - 26 Aug
$184pp
ORF
Norfolk
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk
24 Aug - 31 Aug
$185pp
ORF
Norfolk
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
ORF
Norfolk

Cheap American Airlines flights from Virginia Beach to Chicago

24 Aug - 31 Aug
$185pp
ORF
Norfolk
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
ORF
Norfolk
23 Aug - 30 Aug
$193pp
ORF
Norfolk
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
ORF
Norfolk
26 Aug - 30 Aug
$194pp
ORF
Norfolk
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
ORF
Norfolk

Cheap Frontier flights from Virginia Beach to Chicago

22 Aug - 26 Aug
$184pp
ORF
Norfolk
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk
2 Nov - 9 Nov
$192pp
ORF
Norfolk
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
ORF
Norfolk
2 Nov - 9 Nov
$210pp
ORF
Norfolk
Frontier
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Frontier
 
1 STOP
ORF
Norfolk

Non-stop flights to Chicago from Virginia Beach

Save time with Virginia Beach to Chicago direct flight deals
26 Aug - 29 Aug
$178pp
ORF
Norfolk
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
3 Sep - 10 Sep
$187pp
ORF
Norfolk
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
22 Sep - 26 Sep
$188pp
ORF
Norfolk
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk

Last minute flights from Virginia Beach to Chicago

Late deals on round-trip flights to Chicago from Virginia Beach, departing today and this week
14 Aug - 6 Sep
$281pp
ORF
Norfolk
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
14 Aug - 6 Sep
$288pp
ORF
Norfolk
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ORF
Norfolk
16 Aug - 23 Aug
$296pp
ORF
Norfolk
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
ORF
Norfolk

One-way flights to Chicago from Virginia Beach

The cheapest one-way flights from Virginia Beach to Chicago
4:50 pm - 6:50 am
Multiple Airlines
2 Stops
15h 00m
ORF - ORD
Multiple Airlines
$173
Kiwi.com
9:00 am - 10:24 am
United Airlines
Nonstop
2h 24m
ORF - ORD
United Airlines
$189
United
10:05 am - 1:17 am
Frontier
2 Stops
16h 12m
ORF - MDW
Frontier
$193
StudentUniverse

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Virginia Beach</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Virginia Beach to Chicago

Which airlines flying from Virginia Beach to Chicago have flexible cancellations due to COVID-19?

United Airlines, American Airlines, and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Virginia Beach to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Virginia Beach to Chicago for under $200. The cheapest flight booked recently is on United Airlines for just $178, but on average you can expect to pay $200.

Are there nonstop flights from Virginia Beach to Chicago for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Virginia Beach to Chicago under $200. A good price for a nonstop flight from Virginia Beach to Chicago is less than $262.

Are there last-minute flights available from Virginia Beach to Chicago for under $300?

There are currently 20+ open flights from Virginia Beach to Chicago within the next 7 days for less than $300.

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

To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $89. Frontier flights start at $96 while deals on Delta start at $98 one-way.

What are the cheapest flights from Virginia Beach to Chicago?

The cheapest flight price from Virginia Beach to Chicago is $122. On average you can expect to pay $327. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $185.

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 SkyWest Airlines (100%), Royal Jordanian (90%) and Envoy Air (88%).

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

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

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Virginia Beach?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Virginia Beach need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Virginia Beach are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

Quarantine requirements
Visitors from Virginia Beach are not required to quarantine after entering Chicago.

Do I need a test to fly back to Virginia Beach from Chicago?

Returning to Virginia Beach from Chicago

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Virginia Beach.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Virginia Beach.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for Virginia Beach to Chicago

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

Top 7 airlines flying from Virginia Beach to Chicago

The chart below displays the airlines Cheapflights users traveling from Virginia Beach to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Juneyao Airlines
$17 $24 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Spirit Airlines
$39 $102 No cancel fee 65%
Frontier
$87 $218 No cancel fee 62%
JetBlue
$91 $190 No cancel fee 62%
American Airlines
$98 $353 No cancel fee 71%
Delta
$100 $348 No cancel fee N/A
United Airlines
$141 $303 No cancel fee 69%

Hourly flight availability from Virginia Beach to Chicago

See what time of day planes typically take off from Virginia Beach towards Chicago.
Afternoon Noon to 6 PM 46% of Virginia Beach to CHI departures
Morning 6 AM to noon 30% of Virginia Beach to CHI departures
Early morning Midnight to 6 AM 21% of Virginia Beach to CHI departures
Evening 6 PM to midnight 3% of Virginia Beach to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Virginia Beach to Chicago
See how many times per day planes take to the skies headed from Virginia Beach to Chicago.
Sunday
14 daily flights
Monday
17 daily flights
Tuesday
17 daily flights
Wednesday
17 daily flights
Thursday
17 daily flights
Friday
17 daily flights
Saturday
13 daily flights
Home Flights North America USA Illinois Chicago Cheap flights from Virginia Beach to Chicago