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 7 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?

Delta, Frontier, and Southwest 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 1,262 per week as of May 2026. 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?

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.

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

As of May 2026, there are 180 flights per day flying from Virginia to Chicago. The most common time of day flights depart is 5:00PM, with 54% of flights taking off at noon.

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 May 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.

$67 Cheap Flights from Virginia to Chicago in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

5:48 pm - 11:09 am

RDU

MDW

18h 21m

2 stops

6:00 am - 11:59 am

MDW

RDU

4h 59m

1 stop

$201Frontier

Sun, May 31 - Tue, Jun 2

12:54 pm - 7:29 pm

RDU

ORD

7h 35m

1 stop

4:05 pm - 8:04 am

ORD

RDU

14h 59m

2 stops

$202Frontier

Tue, Jun 2 - Fri, Jun 5

10:03 pm - 10:02 pm

RDU

MDW

24h 59m

2 stops

6:00 am - 12:29 am

MDW

RDU

17h 29m

1 stop

$203Multiple Airlines

Wed, Jun 3 - Tue, Jun 9

5:50 pm - 10:36 pm

DCA

ORD

5h 46m

1 stop

2:00 pm - 6:59 pm

ORD

DCA

3h 59m

1 stop

$228Delta

Wed, May 27 - Thu, Jun 4

6:00 am - 8:45 am

IAD

ORD

3h 45m

1 stop

5:19 pm - 10:56 pm

ORD

IAD

4h 37m

1 stop

$228Delta

Mon, May 25 - Tue, Jun 2

10:10 pm - 11:30 pm

DCA

ORD

2h 20mnonstop

7:10 am - 10:13 am

ORD

DCA

2h 03mnonstop

$231American Airlines

Thu, Jun 25 - Tue, Jun 30

6:30 am - 7:46 am

DCA

ORD

2h 16mnonstop

6:00 am - 8:54 am

ORD

DCA

1h 54mnonstop

$233United Airlines

Wed, Jul 1 - Wed, Jul 8

3:52 pm - 5:25 pm

DCA

ORD

2h 33mnonstop

2:57 pm - 6:00 pm

ORD

DCA

2h 03mnonstop

$234American Airlines

Sat, Jun 13 - Tue, Jun 16

6:15 am - 9:36 am

GSO

ORD

4h 21m

1 stop

6:15 pm - 9:23 pm

ORD

GSO

2h 08mnonstop

$269United Airlines

Tue, Jul 14 - Sat, Jul 18

7:06 pm - 12:25 pm

ORF

ORD

18h 19m

2 stops

1:50 pm - 11:21 am

ORD

ORF

20h 31m

1 stop

$318Multiple Airlines

Wed, Jul 29 - Thu, Aug 6

United Airlines flights from Virginia to Chicago

Our best United Airlines deals on Virginia to Chicago flight tickets

United Airlines

Jul 1

DCA8:10 pmWashington, D.C. Reagan-National

2h 22m

ORD9:32 pmChicago O'Hare Intl

Aug 15

ORD4:00 pmChicago O'Hare Intl

1h 52m

DCA6:52 pmWashington, D.C. Reagan-National

$233

United Airlines

May 28

IAD10:15 pmWashington, D.C. Dulles Intl

2h 11m

ORD11:26 pmChicago O'Hare Intl

Jun 1

ORD9:55 pmChicago O'Hare Intl

2h 04m

IAD12:59 amWashington, D.C. Dulles Intl

$239

United Airlines

Jun 9

IAD8:15 amWashington, D.C. Dulles Intl

2h 21m

ORD9:36 amChicago O'Hare Intl

Jun 13

ORD3:53 pmChicago O'Hare Intl

2h 09m

IAD7:02 pmWashington, D.C. Dulles Intl

$243

American Airlines flights from Virginia to Chicago

Our best American Airlines deals on Virginia to Chicago flight tickets

American Airlines

Jun 25

DCA10:10 pmWashington, D.C. Reagan-National

2h 20m

ORD11:30 pmChicago O'Hare Intl

Jun 30

ORD7:10 amChicago O'Hare Intl

2h 03m

DCA10:13 amWashington, D.C. Reagan-National

$231

American Airlines

Jun 13

DCA3:52 pmWashington, D.C. Reagan-National

2h 33m

ORD5:25 pmChicago O'Hare Intl

Jun 16

ORD2:57 pmChicago O'Hare Intl

2h 03m

DCA6:00 pmWashington, D.C. Reagan-National

$234

American Airlines

Jul 1

DCA11:35 amWashington, D.C. Reagan-National

2h 22m

ORD12:57 pmChicago O'Hare Intl

Aug 15

ORD6:40 amChicago O'Hare Intl

3h 35m

1 stop

DCA11:15 amWashington, D.C. Reagan-National

$243

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 5/31

5:48 pm-11:09 am

2 stops18h 21m

Chicago Midway

Tue 6/2

6:00 am-11:59 am

1 stop4h 59m

$201

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Tue 6/2

12:54 pm-7:29 pm

1 stop7h 35m

Chicago O'Hare Intl

Fri 6/5

4:05 pm-8:04 am

2 stops14h 59m

$202

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 6/3

10:03 pm-10:02 pm

2 stops24h 59m

Chicago Midway

Tue 6/9

6:00 am-12:29 am

1 stop17h 29m

$203

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 5/27

5:50 pm-10:36 pm

1 stop5h 46m

Chicago O'Hare Intl

Thu 6/4

2:00 pm-6:59 pm

1 stop3h 59m

$228

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 5/25

6:00 am-8:45 am

1 stop3h 45m

Chicago O'Hare Intl

Tue 6/2

5:19 pm-10:56 pm

1 stop4h 37m

$228

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 6/25

10:10 pm-11:30 pm

Nonstop2h 20m

Chicago O'Hare Intl

Tue 6/30

7:10 am-10:13 am

Nonstop2h 03m

$231

Quickest round-trip

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 7/1

6:30 am-7:46 am

Nonstop2h 16m

Chicago O'Hare Intl

Wed 7/8

6:00 am-8:54 am

Nonstop1h 54m

$233

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 6/13

3:52 pm-5:25 pm

Nonstop2h 33m

Chicago O'Hare Intl

Tue 6/16

2:57 pm-6:00 pm

Nonstop2h 03m

$234

GreensboroChicago

GSO - ORD

GSOORD

Greensboro/H. Point

Tue 7/14

6:15 am-9:36 am

1 stop4h 21m

Chicago O'Hare Intl

Sat 7/18

6:15 pm-9:23 pm

Nonstop2h 08m

$269

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 7/29

7:06 pm-12:25 pm

2 stops18h 19m

Chicago O'Hare Intl

Thu 8/6

1:50 pm-11:21 am

1 stop20h 31m

$318

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 May is, on average, the cheapest month to fly to Chicago from Virginia, with most prices found around $65. If you’re not able to fly to Chicago in May, then August is your next best option. Flight prices from Virginia to Chicago during August average around $70.

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 $450. 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 $625.

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 $449. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $507.

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 from Virginia 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 $373 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 $267 on momondo.

Can stopping save me money on Virginia to Chicago flights?

You could potentially save up to 6% 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	$193
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 $193. The best round-trip flight deal from Virginia to Chicago found on momondo in the last 72 hours is $307.

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

Frequently asked questions about flying from Virginia to 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 7 operators available for flights from Virginia to Chicago as of May 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 Embraer 175, making up 17.31% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 16.88%, Canadair (Bombardier) Regional Jet CRJ-550 with 12.75%, and Embraer 170 with 8.71%.

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
Frontier	PriceFrom $72	Free Cancellation	Rating 5.6 2,964 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $92	Free Cancellation	Rating 6.3 8,638 reviews	Search Spirit Airlines flights
Delta	PriceFrom $108	Free Cancellation	Rating 7.9 8,460 reviews	Search Delta flights
JetBlue	PriceFrom $126	Free Cancellation	Rating 7.1 2,980 reviews	Search JetBlue flights
Southwest	PriceFrom $178	Free Cancellation	Rating 7.9 4,303 reviews	Search Southwest flights
American Airlines	PriceFrom $203	Free Cancellation	Rating 7.1 11,669 reviews	Search American Airlines flights
United Airlines	PriceFrom $209	Free Cancellation	Rating 7.4 9,690 reviews	Search United Airlines flights

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

Crown Point

Monticello

Chesterton

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.

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Sat 6/6

Sat 6/13

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Virginia

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Virginia to Chicago from $67

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 5/28. 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

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Virginia to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

United Airlines flights from Virginia to Chicago

Our best United Airlines deals on Virginia to Chicago flight tickets

American Airlines flights from Virginia to Chicago

Our best American Airlines deals on Virginia to Chicago flight tickets

momondo Fare Finder

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

What is the cheapest month to fly to Chicago?

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?

What is the cheapest Virginia to Chicago flight route?

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

Can stopping save me money on Virginia to Chicago flights?

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

What airlines fly to Chicago?

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

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

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

Frequently asked questions about flying 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?

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.

Popular cities in the United States

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

Fly to other destinations from Virginia

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year