How many flights depart from Virginia to Chicago on average per day?

As of September 2025, there are 116 flights per day flying from Virginia to Chicago. The most common time of day flights depart is 6:00AM, with 55% of flights taking off at noon.

What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Virginia according to our data. United Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Virginia to Chicago?

Frontier, Spirit Airlines, and JetBlue are the most popular carriers operating from Virginia to Chicago

How long does it take to fly to Chicago?

Average flight duration from Virginia to Chicago depends on which airport you fly into and out of. Flying from Roanoke to Chicago O'Hare Intl Airport is 1h 53m on average, while flying from Charlottesville to Chicago O'Hare Intl Airport is 2h 05m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

How many flights depart from Virginia to Chicago on average per week?

The number of flights available between Virginia and Chicago is 815 per week as of September 2025. The most frequent departure day is Tue, with 23% of weekly flights leaving on this day.

When did momondo last update prices for flights from Virginia to Chicago?

Prices for flights from Virginia to Chicago refresh daily.

How many operators does momondo search for flights from Virginia to Chicago?

There are 6 operators available for flights from Virginia to Chicago as of September 2025.

How old do you have to be to fly from Virginia to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Virginia to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$72 Cheap Flights from Virginia to Chicago in 2025/26

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Find the cheapest flights from Virginia to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

9:44 pm - 11:06 pmRDU-ORD

2h 22mnonstop

2:41 pm - 5:47 pmORD-RDU

2h 06mnonstop

$127Frontier

Find Deal

Sun, Oct 12 - Fri, Oct 17

9:44 pm - 11:06 pmRDU-ORD

2h 22mnonstop

6:00 am - 1:32 pmORD-RDU

6h 32m1 stop

$128Frontier

Find Deal

Sun, Oct 12 - Fri, Oct 24

10:06 pm - 11:28 pmRDU-ORD

2h 22mnonstop

8:50 pm - 11:55 pmORD-RDU

26h 05m1 stop

$130Multiple Airlines

Find Deal

Mon, Nov 3 - Wed, Nov 5

6:15 am - 7:38 amRDU-ORD

2h 23mnonstop

2:20 pm - 5:23 pmORD-RDU

2h 03mnonstop

$139United Airlines

Find Deal

Wed, Oct 22 - Wed, Oct 29

6:00 am - 6:55 amRDU-MDW

1h 55mnonstop

9:55 am - 12:45 pmMDW-RDU

1h 50mnonstop

$139Southwest

Find Deal

Wed, Oct 29 - Sat, Nov 1

10:48 am - 9:23 pmRDU-ORD

11h 35m1 stop

4:16 pm - 7:21 pmORD-RDU

2h 05mnonstop

$147Multiple Airlines

Find Deal

Tue, Dec 9 - Sun, Dec 14

10:00 am - 11:32 amRDU-ORD

2h 32mnonstop

7:10 am - 10:14 amORD-RDU

2h 04mnonstop

$158United Airlines

Find Deal

Sat, Oct 25 - Mon, Oct 27

12:05 pm - 1:05 pmRDU-MDW

2h 00mnonstop

5:45 pm - 8:35 pmMDW-RDU

1h 50mnonstop

$158Southwest

Find Deal

Thu, Oct 23 - Sat, Oct 25

6:25 pm - 11:05 pmRDU-ORD

5h 40m1 stop

8:41 am - 4:24 pmORD-RDU

6h 43m1 stop

$183Spirit Airlines

Find Deal

Thu, Dec 11 - Mon, Dec 15

10:09 am - 6:38 pmRIC-ORD

9h 29m1 stop

11:55 am - 7:55 pmORD-RIC

7h 00m1 stop

$204Spirit Airlines

Find Deal

Mon, Oct 20 - Sun, Oct 26

American Airlines flights from Virginia to Chicago

Our best American Airlines deals on Virginia to Chicago flight tickets

American Airlines

Oct 25

GSO7:30 amGreensboro/H. Point

2h 08m

ORD8:38 amChicago O'Hare Intl

Oct 27

ORD4:50 pmChicago O'Hare Intl

1h 57m

GSO7:47 pmGreensboro/H. Point

$204

Find similar

American Airlines

Dec 6

ROA8:12 amRoanoke

5h 15m

1 stop

ORD12:27 pmChicago O'Hare Intl

Dec 8

ORD9:04 pmChicago O'Hare Intl

1h 55m

ROA11:59 pmRoanoke

$230

Find similar

American Airlines

Oct 31

GSO7:30 amGreensboro/H. Point

2h 08m

ORD8:38 amChicago O'Hare Intl

Nov 2

ORD8:10 amChicago O'Hare Intl

1h 57m

GSO11:07 amGreensboro/H. Point

$235

Find similar

Frontier flights from Virginia to Chicago

Our best Frontier deals on Virginia to Chicago flight tickets

Frontier

Oct 12

RDU9:44 pmRaleigh-Durham

2h 22m

ORD11:06 pmChicago O'Hare Intl

Oct 17

ORD2:41 pmChicago O'Hare Intl

2h 06m

RDU5:47 pmRaleigh-Durham

$127

Find similar

Frontier

Oct 12

RDU9:44 pmRaleigh-Durham

2h 22m

ORD11:06 pmChicago O'Hare Intl

Oct 24

ORD6:00 amChicago O'Hare Intl

6h 32m

1 stop

RDU1:32 pmRaleigh-Durham

$128

Find similar

Frontier

Sep 29

RDU3:35 pmRaleigh-Durham

2h 16m

ORD4:51 pmChicago O'Hare Intl

Oct 2

ORD11:36 amChicago O'Hare Intl

2h 14m

RDU2:50 pmRaleigh-Durham

$130

Find similar

Fly from

Fly to

Route

Depart

Return

Price

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sun 10/12

9:44 pm-11:06 pm

Nonstop2h 22m

Chicago O'Hare Intl

Fri 10/17

2:41 pm-5:47 pm

Nonstop2h 06m

$127

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sun 10/12

9:44 pm-11:06 pm

Nonstop2h 22m

Chicago O'Hare Intl

Fri 10/24

6:00 am-1:32 pm

1 stop6h 32m

$128

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Mon 11/3

10:06 pm-11:28 pm

Nonstop2h 22m

Chicago O'Hare Intl

Wed 11/5

8:50 pm-11:55 pm

1 stop26h 05m

$130

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 10/22

6:15 am-7:38 am

Nonstop2h 23m

Chicago O'Hare Intl

Wed 10/29

2:20 pm-5:23 pm

Nonstop2h 03m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 10/29

6:00 am-6:55 am

Nonstop1h 55m

Chicago Midway

Sat 11/1

9:55 am-12:45 pm

Nonstop1h 50m

$139

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Tue 12/9

10:48 am-9:23 pm

1 stop11h 35m

Chicago O'Hare Intl

Sun 12/14

4:16 pm-7:21 pm

Nonstop2h 05m

$147

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 10/25

10:00 am-11:32 am

Nonstop2h 32m

Chicago O'Hare Intl

Mon 10/27

7:10 am-10:14 am

Nonstop2h 04m

$158

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 10/23

12:05 pm-1:05 pm

Nonstop2h 00m

Chicago Midway

Sat 10/25

5:45 pm-8:35 pm

Nonstop1h 50m

$158

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 12/11

6:25 pm-11:05 pm

1 stop5h 40m

Chicago O'Hare Intl

Mon 12/15

8:41 am-4:24 pm

1 stop6h 43m

$183

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Mon 10/20

10:09 am-6:38 pm

1 stop9h 29m

Chicago O'Hare Intl

Sun 10/26

11:55 am-7:55 pm

1 stop7h 00m

$204

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Virginia to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Virginia, with most prices found around $320. If you’re not able to fly to Chicago in October, then March is your next best option. Flight prices from Virginia to Chicago during March average around $338.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $468. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Virginia to Chicago for around $619.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Virginia to Chicago during this time can be as low as $462. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $513.

What is the cheapest Virginia to Chicago flight route?

Fly from Richmond Byrd Intl to Chicago Midway for the best Virginia - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Virginia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $370 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Virginia for as low as $243 on momondo.

What cabin class options are available on Virginia to Chicago flights?

There are 4 cabin classes available to choose from on Virginia to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Virginia to Chicago flights?

No. A direct flight is the cheapest option for a flight between Virginia to Chicago.

Cheap Virginia to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Virginia to Chicago

Best Price Found	$128
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Virginia in the past 72 hours is $128. The best round-trip flight deal from Virginia to Chicago found on momondo in the last 72 hours is $283.

The fastest flight from Virginia to Chicago takes 1h 55m

Direct flights go from Virginia to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Virginia to Chicago?
Prices for flights from Virginia to Chicago refresh daily.
How many operators does momondo search for flights from Virginia to Chicago?
There are 6 operators available for flights from Virginia to Chicago as of September 2025.
How old do you have to be to fly from Virginia to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Virginia to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Virginia to Chicago?
Based on momondo bookings for flights between Virginia and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 19.00% of the total bookings. Other popular models include Canadair (Bombardier) Regional Jet CRJ-550 with 16.03%, Canadair (Bombardier) Regional Jet 700 with 11.33%, and Embraer 175 with 11.05%.

Best airlines flying from Virginia to Chicago

Compare and see reviews for airlines that fly from Virginia to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $65	Free Cancellation	Rating 6.3 8,041 reviews	Search Spirit Airlines flights
Delta	PriceFrom $98	Free Cancellation	Rating 7.9 7,974 reviews	Search Delta flights
Frontier	PriceFrom $168	Free Cancellation	Rating 5.8 3,165 reviews	Search Frontier flights
American Airlines	PriceFrom $209	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $209	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights
Southwest	PriceFrom $229	Free Cancellation	Rating 8.0 4,244 reviews	Search Southwest flights

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Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Virginia to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Virginia to Chicago for you.

Can I find flights from Virginia to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Virginia on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Virginia to Chicago?

momondo helps you find the best flight between Virginia and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Virginia to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Virginia to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Denverfrom $82

Cheap flights from Virginia to Chicago from $72

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Virginia to Chicago departing on 10/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Find the cheapest flights from Virginia to Chicago

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

American Airlines flights from Virginia to Chicago

Our best American Airlines deals on Virginia to Chicago flight tickets

Frontier flights from Virginia to Chicago

Our best Frontier deals on Virginia to Chicago flight tickets

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Use the filters below to find and compare flights from Virginia to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Virginia to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Virginia, with most prices found around $320. If you’re not able to fly to Chicago in October, then March is your next best option. Flight prices from Virginia to Chicago during March average around $338.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Virginia to Chicago during this time can be as low as $462. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $513.

What is the cheapest Virginia to Chicago flight route?

Fly from Richmond Byrd Intl to Chicago Midway for the best Virginia - Chicago flight prices

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

What cabin class options are available on Virginia to Chicago flights?

There are 4 cabin classes available to choose from on Virginia to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Virginia to Chicago flights?

No. A direct flight is the cheapest option for a flight between Virginia to Chicago.

What is the cheapest airline that flies from Virginia to Chicago?

Frontier, Spirit Airlines, and JetBlue are the most popular carriers operating from Virginia to Chicago

What airlines fly to Chicago?

How many flights depart from Virginia to Chicago on average per day?

As of September 2025, there are 116 flights per day flying from Virginia to Chicago. The most common time of day flights depart is 6:00AM, with 55% of flights taking off at noon.

How many flights depart from Virginia to Chicago on average per week?

The number of flights available between Virginia and Chicago is 815 per week as of September 2025. The most frequent departure day is Tue, with 23% of weekly flights leaving on this day.

How long does it take to fly to Chicago?

Cheap Virginia to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Virginia to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Virginia to Chicago?

How many operators does momondo search for flights from Virginia to Chicago?

How old do you have to be to fly from Virginia to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Virginia to Chicago?

Best airlines flying from Virginia to Chicago

Compare and see reviews for airlines that fly from Virginia to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Virginia to Chicago?

Can I find flights from Virginia to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Virginia to Chicago?

I’m not ready to book a flight from Virginia to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago