Cheap flights from Virginia (VA) 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

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

All the information you need to plan the best null to CHI flight in 2022: compare Virginia to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
What is the cheapest month to fly from Virginia to Chicago?

The best pricing can be found in the month of February. Prices to Chicago from Virginia 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. Flying in the targeted month can save you up to 29%.

When is the cheapest time to fly from Virginia to Chicago (VA - CHI)?

When flying from Virginia to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Find a great deal and save up to 31% by booking at least 24 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Virginia to Chicago within the next two weeks, with the cheapest ticket starting at $314.

Cheap flights from Virginia to Chicago in August, September 2022

The best prices found for Virginia to CHI flights for August, September
14 Sep - 20 Sep
$152pp
RIC
Richmond Byrd Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
RIC
Richmond Byrd Intl
14 Sep - 27 Sep
$155pp
RIC
Richmond Byrd Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
RIC
Richmond Byrd Intl
14 Sep - 20 Sep
$159pp
RIC
Richmond Byrd Intl
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
RIC
Richmond Byrd Intl

Virginia to Chicago 2022 flight deals

Cheap flights to Chicago from Virginia found for this year
12 Oct - 12 Oct
$150pp
RIC
Richmond Byrd Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
RIC
Richmond Byrd Intl
14 Sep - 20 Sep
$152pp
RIC
Richmond Byrd Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
RIC
Richmond Byrd Intl
14 Sep - 27 Sep
$155pp
RIC
Richmond Byrd Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
RIC
Richmond Byrd Intl

Cheap American Airlines flights from Virginia to Chicago

12 Oct - 12 Oct
$150pp
RIC
Richmond Byrd Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
RIC
Richmond Byrd Intl
21 Sep - 22 Sep
$156pp
RIC
Richmond Byrd Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
RIC
Richmond Byrd Intl
16 Aug - 17 Aug
$176pp
RIC
Richmond Byrd Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
RIC
Richmond Byrd Intl

Cheap Spirit Airlines flights from Virginia to Chicago

14 Sep - 20 Sep
$152pp
RIC
Richmond Byrd Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
RIC
Richmond Byrd Intl
14 Sep - 27 Sep
$155pp
RIC
Richmond Byrd Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
RIC
Richmond Byrd Intl
14 Sep - 20 Sep
$159pp
RIC
Richmond Byrd Intl
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
RIC
Richmond Byrd Intl

Non-stop flights to Chicago from Virginia

Save time with Virginia to Chicago direct flight deals
6 Sep - 9 Sep
$168pp
ROA
Roanoke
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ROA
Roanoke
26 Oct - 1 Nov
$175pp
ROA
Roanoke
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
ROA
Roanoke
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

Last minute flights from Virginia to Chicago

Late deals on round-trip flights to Chicago from Virginia, departing today and this week
16 Aug - 17 Aug
$176pp
RIC
Richmond Byrd Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
RIC
Richmond Byrd Intl
16 Aug - 17 Aug
$187pp
RIC
Richmond Byrd Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
RIC
Richmond Byrd Intl
16 Aug - 23 Aug
$191pp
RIC
Richmond Byrd Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
RIC
Richmond Byrd Intl

One-way flights to Chicago from Virginia

The cheapest one-way flights from Virginia to Chicago
2:40 am - 9:40 am
Delta
1 Stop
8h 00m
ORF - ORD
Delta
$98
Delta
6:50 am - 1:57 pm
JetBlue
1 Stop
8h 07m
RIC - ORD
JetBlue
9:23 am - 10:41 am
United Airlines
Nonstop
2h 18m
ORF - ORD
United Airlines
$111
United

Related info for your journey

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

Flight FAQs

From Virginia to Chicago

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

Some of the carriers operating flights from Virginia to Chicago that may be offering flexible cancellation policies are United Airlines, American Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

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

Yes, there are multiple flights from Virginia to Chicago for under $200. The cheapest flight booked recently is on American Airlines for just $150, but on average you can expect to pay $172.

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

Cheapflights has at least 20 direct flights from Virginia to Chicago under $200. A good price for a nonstop flight from Virginia to Chicago is less than $217.

Are there last-minute flights available from Virginia to Chicago for under $200?

There are currently 20+ open flights from Virginia to Chicago within the next 7 days for less than $200.

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

The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $68. However, be on the lookout for offers from United Airlines and Frontier, as they are both options that can get you from Virginia to Chicago for a low price.

What are the most popular routes from Virginia to Chicago?

When deciding which route to take from Virginia to Chicago consider Richmond Byrd Intl - Chicago O'Hare Intl, Norfolk - Chicago O'Hare Intl or Richmond Byrd Intl - Chicago Midway as they are the most popular.

What are the cheapest flights from Virginia to Chicago?

While on average a flight from Virginia to Chicago is generally $327, our data shows the cheapest flight currently is $122. When looking at the most popular route, (Richmond Byrd Intl - Chicago O'Hare Intl), you can expect to pay $152 for that flight.

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

Before booking your flight from Virginia to Chicago check out the most popular airlines for this route: American Airlines, JetBlue or Delta.

What are the most reliable airlines from Virginia to Chicago?

Consider SkyWest Airlines (100%), Royal Jordanian (90%) or Envoy Air (88%) when booking your flight. These represent the most reliable airlines when flying from Virginia to Chicago.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

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

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

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

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

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

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

Returning to Virginia 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.

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

Hide COVID Travel Restrictions for Chicago, IL

Departure points for flights from Virginia to Chicago

Select to see more specific information for flights to Chicago from all departure points in Virginia.

Top 7 airlines flying from Virginia to Chicago

The chart below displays the airlines Cheapflights users traveling from Virginia 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 $369 No cancel fee 71%
Delta
$100 $387 No cancel fee N/A
United Airlines
$141 $320 No cancel fee 69%