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 48% 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?

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

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

The number of flights available between Virginia and Chicago is 1,043 per week as of November 2025. The most frequent departure day is Thu, with 17% of weekly flights leaving on this day.

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

As of November 2025, there are 149 flights per day flying from Virginia to Chicago. The most common time of day flights depart is 6:00AM, with 47% of flights taking off in the afternoon.

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 1h 58m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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 November 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.

$55 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

Enter your travel dates to find the best prices.

1:58 pm - 3:23 pmRDU-ORD

2h 25mnonstop

5:30 am - 2:05 pmORD-RDU

7h 35m1 stop

$126Frontier

Find Deal

Thu, Nov 20 - Mon, Nov 24

5:33 pm - 12:10 amRDU-ORD

7h 37m1 stop

11:44 am - 12:12 amORD-RDU

11h 28m1 stop

$127Frontier

Find Deal

Sat, Nov 22 - Mon, Dec 15

5:10 pm - 6:15 pmRDU-MDW

2h 05mnonstop

9:50 am - 12:45 pmMDW-RDU

1h 55mnonstop

$139Southwest

Find Deal

Sat, Dec 6 - Sat, Dec 13

1:40 pm - 2:45 pmRDU-MDW

2h 05mnonstop

10:00 am - 1:00 pmMDW-RDU

2h 00mnonstop

$149Southwest

Find Deal

Tue, Dec 2 - Tue, Dec 9

6:20 am - 7:46 amRDU-ORD

2h 26mnonstop

2:05 pm - 5:08 pmORD-RDU

2h 03mnonstop

$149United Airlines

Find Deal

Tue, Dec 2 - Tue, Dec 9

10:00 am - 11:25 amRDU-ORD

2h 25mnonstop

7:10 am - 10:14 amORD-RDU

2h 04mnonstop

$158United Airlines

Find Deal

Sat, Dec 6 - Thu, Dec 11

9:00 am - 2:31 pmIAD-ORD

6h 31m1 stop

7:41 pm - 4:24 pmORD-IAD

19h 43m2 stops

$160Multiple Airlines

Find Deal

Wed, Dec 10 - Sat, Dec 13

8:44 am - 11:06 pmIAD-ORD

15h 22m1 stop

4:22 pm - 2:29 pmORD-IAD

21h 07m1 stop

$162Multiple Airlines

Find Deal

Sun, Nov 23 - Tue, Dec 2

4:55 pm - 8:52 pmDCA-ORD

4h 57m1 stop

1:43 pm - 10:59 pmORD-DCA

8h 16m1 stop

$169JetBlue

Find Deal

Tue, Nov 18 - Thu, Nov 20

6:15 am - 1:10 pmDCA-ORD

7h 55m1 stop

2:05 pm - 10:47 pmORD-DCA

7h 42m1 stop

$177JetBlue

Find Deal

Fri, Jan 9 - Sat, Jan 10

Frontier flights from Virginia to Chicago

Our best Frontier deals on Virginia to Chicago flight tickets

Frontier

Nov 20

RDU1:58 pmRaleigh-Durham

2h 25m

ORD3:23 pmChicago O'Hare Intl

Nov 24

ORD5:30 amChicago O'Hare Intl

7h 35m

1 stop

RDU2:05 pmRaleigh-Durham

$126

Find similar

Frontier

Nov 22

RDU5:33 pmRaleigh-Durham

7h 37m

1 stop

ORD12:10 amChicago O'Hare Intl

Dec 15

ORD11:44 amChicago O'Hare Intl

11h 28m

1 stop

RDU12:12 amRaleigh-Durham

$127

Find similar

Frontier

Nov 18

RDU6:10 amRaleigh-Durham

6h 04m

1 stop

ORD11:14 amChicago O'Hare Intl

Nov 20

ORD6:00 amChicago O'Hare Intl

11h 19m

1 stop

RDU6:19 pmRaleigh-Durham

$128

Find similar

Spirit Airlines flights from Virginia to Chicago

Our best Spirit Airlines deals on Virginia to Chicago flight tickets

Spirit Airlines

Dec 3

ORF8:02 pmNorfolk

25h 07m

3 stops

ORD8:09 pmChicago O'Hare Intl

Dec 6

ORD7:10 amChicago O'Hare Intl

11h 06m

1 stop

ORF7:16 pmNorfolk

$191

Find similar

Spirit Airlines

Jan 9

ORF6:45 amNorfolk

12h 07m

1 stop

ORD5:52 pmChicago O'Hare Intl

Jan 11

ORD12:44 pmChicago O'Hare Intl

8h 04m

1 stop

ORF9:48 pmNorfolk

$193

Find similar

Spirit Airlines

Dec 5

ORF8:38 amNorfolk

6h 43m

1 stop

ORD2:21 pmChicago O'Hare Intl

Dec 7

ORD1:52 pmChicago O'Hare Intl

16h 51m

2 stops

ORF7:43 amNorfolk

$196

Find similar

Fly from

Fly to

Route

Depart

Return

Price

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 11/20

1:58 pm-3:23 pm

Nonstop2h 25m

Chicago O'Hare Intl

Mon 11/24

5:30 am-2:05 pm

1 stop7h 35m

$126

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 11/22

5:33 pm-12:10 am

1 stop7h 37m

Chicago O'Hare Intl

Mon 12/15

11:44 am-12:12 am

1 stop11h 28m

$127

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Sat 12/13

9:50 am-12:45 pm

Nonstop1h 55m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 12/2

1:40 pm-2:45 pm

Nonstop2h 05m

Chicago Midway

Tue 12/9

10:00 am-1:00 pm

Nonstop2h 00m

$149

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Tue 12/2

6:20 am-7:46 am

Nonstop2h 26m

Chicago O'Hare Intl

Tue 12/9

2:05 pm-5:08 pm

Nonstop2h 03m

$149

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 12/6

10:00 am-11:25 am

Nonstop2h 25m

Chicago O'Hare Intl

Thu 12/11

7:10 am-10:14 am

Nonstop2h 04m

$158

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 12/10

9:00 am-2:31 pm

1 stop6h 31m

Chicago O'Hare Intl

Sat 12/13

7:41 pm-4:24 pm

2 stops19h 43m

$160

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 11/23

8:44 am-11:06 pm

1 stop15h 22m

Chicago O'Hare Intl

Tue 12/2

4:22 pm-2:29 pm

1 stop21h 07m

$162

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 11/18

4:55 pm-8:52 pm

1 stop4h 57m

Chicago O'Hare Intl

Thu 11/20

1:43 pm-10:59 pm

1 stop8h 16m

$169

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 1/9

6:15 am-1:10 pm

1 stop7h 55m

Chicago O'Hare Intl

Sat 1/10

2:05 pm-10:47 pm

1 stop7h 42m

$177

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 $312.

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 $465. 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 $607.

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 $450. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $519.

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 $223 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 49% 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	$137
Fastest flight time	1h 53m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Virginia in the past 72 hours is $137. The best round-trip flight deal from Virginia to Chicago found on momondo in the last 72 hours is $302.

The fastest flight from Virginia to Chicago takes 1h 53m

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 November 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 20.99% of the total bookings. Other popular models include Canadair (Bombardier) Regional Jet CRJ-550 with 16.84%, Canadair (Bombardier) Regional Jet 700 with 11.52%, and Embraer 175 with 11.45%.

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 8,122 reviews	Search Spirit Airlines flights
Delta	PriceFrom $108	Free Cancellation	Rating 7.9 8,001 reviews	Search Delta flights
Frontier	PriceFrom $168	Free Cancellation	Rating 5.8 3,116 reviews	Search Frontier flights
American Airlines	PriceFrom $209	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights
United Airlines	PriceFrom $215	Free Cancellation	Rating 7.4 9,007 reviews	Search United Airlines flights
Southwest	PriceFrom $229	Free Cancellation	Rating 8.0 4,241 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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Cheap flights from Virginia to Chicago from $55

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 1/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

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

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Frontier flights from Virginia to Chicago

Our best Frontier deals on Virginia to Chicago flight tickets

Spirit Airlines flights from Virginia to Chicago

Our best Spirit 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.

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 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 $312.

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 $450. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $519.

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?

You could potentially save up to 49% on your flight if you consider stops on a Virginia to Chicago flight.

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

Spirit Airlines, Frontier, and United 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 November 2025, there are 149 flights per day flying from Virginia to Chicago. The most common time of day flights depart is 6:00AM, with 47% of flights taking off in the afternoon.

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

The number of flights available between Virginia and Chicago is 1,043 per week as of November 2025. The most frequent departure day is Thu, with 17% 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