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 51% 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, United Airlines, and Spirit Airlines 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 2h 04m on average, while flying from Charlottesville to Chicago O'Hare Intl Airport is 2h 10m 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 day?

As of February 2026, there are 110 flights per day flying from Virginia to Chicago. The most common time of day flights depart is 12:00PM, with 47% 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 774 per week as of February 2026. The most frequent departure day is Sun, with 21% 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 7 operators available for flights from Virginia to Chicago as of February 2026.

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.

$39 Cheap Flights from Virginia to Chicago in 2026

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Find the cheapest flights from Virginia to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:31 pm - 11:22 am

ORF

ORD

16h 51m

1 stop

7:00 am - 6:26 pm

ORD

ORF

10h 26m

1 stop

$145Spirit Airlines

Fri, Mar 6 - Wed, Mar 11

1:02 pm - 3:52 pm

ORF

ORD

27h 50m

1 stop

6:02 pm - 10:51 am

ORD

ORF

15h 49m

1 stop

$157Frontier

Tue, Feb 24 - Wed, Feb 25

4:07 pm - 10:19 pm

RDU

MDW

7h 12m

1 stop

7:30 am - 5:29 pm

MDW

RDU

8h 59m

1 stop

$158Multiple Airlines

Fri, Mar 13 - Tue, Mar 17

10:07 pm - 11:37 pm

RDU

ORD

2h 30mnonstop

8:16 pm - 5:59 pm

ORD

RDU

20h 43m

2 stops

$159Multiple Airlines

Mon, Feb 23 - Thu, Feb 26

6:15 am - 11:54 am

RDU

ORD

6h 39m

1 stop

6:04 am - 2:47 pm

ORD

RDU

7h 43m

1 stop

$161JetBlue

Thu, Feb 26 - Mon, Mar 2

7:00 pm - 8:35 pm

DCA

ORD

2h 35mnonstop

7:40 pm - 10:52 pm

ORD

DCA

2h 12mnonstop

$175United Airlines

Sat, Mar 7 - Sat, Mar 14

6:30 am - 7:50 am

DCA

ORD

2h 20mnonstop

7:00 am - 9:54 am

ORD

DCA

1h 54mnonstop

$177United Airlines

Wed, Mar 4 - Sat, Mar 7

5:33 pm - 7:08 pm

DCA

ORD

2h 35mnonstop

8:58 pm - 11:50 pm

ORD

DCA

1h 52mnonstop

$182American Airlines

Sat, Feb 28 - Tue, Mar 3

3:21 pm - 4:45 pm

DCA

ORD

2h 24mnonstop

11:50 am - 2:41 pm

ORD

DCA

1h 51mnonstop

$184American Airlines

Sat, Feb 28 - Wed, Apr 1

8:50 am - 10:59 pm

RIC

ORD

15h 09m

2 stops

10:00 am - 7:27 pm

ORD

RIC

8h 27m

1 stop

$303JetBlue

Thu, Mar 5 - Sat, Mar 7

United Airlines flights from Virginia to Chicago

Our best United Airlines deals on Virginia to Chicago flight tickets

United Airlines

Mar 7

DCA7:00 pmWashington, D.C. Reagan-National

2h 35m

ORD8:35 pmChicago O'Hare Intl

Mar 14

ORD7:40 pmChicago O'Hare Intl

2h 12m

DCA10:52 pmWashington, D.C. Reagan-National

$175

United Airlines

Mar 4

DCA6:30 amWashington, D.C. Reagan-National

2h 20m

ORD7:50 amChicago O'Hare Intl

Mar 7

ORD7:00 amChicago O'Hare Intl

1h 54m

DCA9:54 amWashington, D.C. Reagan-National

$177

United Airlines

Jul 29

DCA6:30 amWashington, D.C. Reagan-National

2h 16m

ORD7:46 amChicago O'Hare Intl

Aug 1

ORD7:00 amChicago O'Hare Intl

1h 59m

DCA9:59 amWashington, D.C. Reagan-National

$196

American Airlines flights from Virginia to Chicago

Our best American Airlines deals on Virginia to Chicago flight tickets

American Airlines

Feb 28

DCA5:33 pmWashington, D.C. Reagan-National

2h 35m

ORD7:08 pmChicago O'Hare Intl

Mar 3

ORD8:58 pmChicago O'Hare Intl

1h 52m

DCA11:50 pmWashington, D.C. Reagan-National

$182

American Airlines

Feb 28

DCA3:21 pmWashington, D.C. Reagan-National

2h 24m

ORD4:45 pmChicago O'Hare Intl

Apr 1

ORD11:50 amChicago O'Hare Intl

1h 51m

DCA2:41 pmWashington, D.C. Reagan-National

$184

American Airlines

Apr 11

DCA1:45 pmWashington, D.C. Reagan-National

2h 24m

ORD3:09 pmChicago O'Hare Intl

Apr 18

ORD9:01 pmChicago O'Hare Intl

1h 56m

DCA11:57 pmWashington, D.C. Reagan-National

$185

Fly from

Fly to

Route

Depart

Return

Price

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 3/6

7:31 pm-11:22 am

1 stop16h 51m

Chicago O'Hare Intl

Wed 3/11

7:00 am-6:26 pm

1 stop10h 26m

$145

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 2/24

1:02 pm-3:52 pm

1 stop27h 50m

Chicago O'Hare Intl

Wed 2/25

6:02 pm-10:51 am

1 stop15h 49m

$157

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 3/13

4:07 pm-10:19 pm

1 stop7h 12m

Chicago Midway

Tue 3/17

7:30 am-5:29 pm

1 stop8h 59m

$158

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Mon 2/23

10:07 pm-11:37 pm

Nonstop2h 30m

Chicago O'Hare Intl

Thu 2/26

8:16 pm-5:59 pm

2 stops20h 43m

$159

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 2/26

6:15 am-11:54 am

1 stop6h 39m

Chicago O'Hare Intl

Mon 3/2

6:04 am-2:47 pm

1 stop7h 43m

$161

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 3/7

7:00 pm-8:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sat 3/14

7:40 pm-10:52 pm

Nonstop2h 12m

$175

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 3/4

6:30 am-7:50 am

Nonstop2h 20m

Chicago O'Hare Intl

Sat 3/7

7:00 am-9:54 am

Nonstop1h 54m

$177

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 2/28

5:33 pm-7:08 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 3/3

8:58 pm-11:50 pm

Nonstop1h 52m

$182

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 2/28

3:21 pm-4:45 pm

Nonstop2h 24m

Chicago O'Hare Intl

Wed 4/1

11:50 am-2:41 pm

Nonstop1h 51m

$184

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Thu 3/5

8:50 am-10:59 pm

2 stops15h 09m

Chicago O'Hare Intl

Sat 3/7

10:00 am-7:27 pm

1 stop8h 27m

$303

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 September is, on average, the cheapest month to fly to Chicago from Virginia, with most prices found around $287. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Virginia to Chicago during October average around $310.

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 $449. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Virginia to Chicago for around $571.

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 $443. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $501.

What is the cheapest Virginia to Chicago flight route?

Fly from Norfolk 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 $359 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?

You could potentially save up to 7% on your flight if you consider stops on a Virginia to Chicago flight.

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	$202
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Virginia in the past 72 hours is $202. The best round-trip flight deal from Virginia to Chicago found on momondo in the last 72 hours is $286.

The fastest flight from Virginia to Chicago takes 1h 50m

Direct flights go from Virginia to Chicago every day.

There are 3 airports in Chicago. From Virginia there are direct flights to 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 7 operators available for flights from Virginia to Chicago as of February 2026.
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 Canadair (Bombardier) Regional Jet CRJ-550, making up 15.52% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 13.50%, Canadair (Bombardier) Regional Jet 700 with 13.01%, and Embraer 175 with 12.30%.

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 $92	Free Cancellation	Rating 6.3 8,430 reviews	Search Spirit Airlines flights
Delta	PriceFrom $108	Free Cancellation	Rating 7.9 8,172 reviews	Search Delta flights
Frontier	PriceFrom $172	Free Cancellation	Rating 5.7 3,052 reviews	Search Frontier flights
Southwest	PriceFrom $178	Free Cancellation	Rating 8.0 4,280 reviews	Search Southwest flights
United Airlines	PriceFrom $191	Free Cancellation	Rating 7.4 9,254 reviews	Search United Airlines flights
American Airlines	PriceFrom $209	Free Cancellation	Rating 7.2 11,249 reviews	Search American Airlines flights

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Porter

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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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Fly into one of these airports located in Chicago

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Cheap flights from Virginia to Chicago from $39

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 2/23. 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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United Airlines flights from Virginia to Chicago

Our best United Airlines deals on Virginia to Chicago flight tickets

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Our best American Airlines 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.

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How to get the cheapest flight ticket from Virginia to Chicago

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Virginia, with most prices found around $287. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Virginia to Chicago during October average around $310.

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 $443. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $501.

What is the cheapest Virginia to Chicago flight route?

Fly from Norfolk 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?

You could potentially save up to 7% on your flight if you consider stops on a Virginia to Chicago flight.

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

Frontier, United Airlines, and Spirit Airlines 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 February 2026, there are 110 flights per day flying from Virginia to Chicago. The most common time of day flights depart is 12:00PM, with 47% 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 774 per week as of February 2026. The most frequent departure day is Sun, with 21% 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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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