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

Delta, United Airlines, 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 1,249 per week as of June 2026. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.

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

As of June 2026, there are 178 flights per day flying from Virginia to Chicago. The most common time of day flights depart is 6:00AM, with 64% of flights taking off at noon.

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 Charlottesville to Chicago O'Hare Intl Airport is 2h 05m on average, while flying from Roanoke to Chicago O'Hare Intl Airport is 2h 08m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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 52% 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.

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 June 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.

$99 Cheap Flights from Virginia to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

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.

5:40 pm - 12:15 pm

IAD

ORD

19h 35m

1 stop

10:16 am - 6:33 pm

ORD

IAD

7h 17m

1 stop

$246Frontier

Tue, Aug 11 - Mon, Aug 17

10:10 pm - 11:30 pm

DCA

ORD

2h 20mnonstop

4:45 pm - 10:20 pm

ORD

DCA

4h 35m

1 stop

$247American Airlines

Sat, Jul 25 - Mon, Jul 27

7:55 pm - 11:15 pm

DCA

MDW

4h 20m

1 stop

6:00 am - 8:45 am

MDW

DCA

1h 45mnonstop

$247Southwest

Wed, Jul 22 - Mon, Jul 27

8:33 pm - 8:02 am

IAD

ORD

12h 29m

1 stop

8:05 am - 7:44 pm

ORD

IAD

10h 39m

1 stop

$247Frontier

Sat, Aug 15 - Thu, Aug 20

12:50 pm - 7:55 pm

DCA

ORD

8h 05m

1 stop

10:56 am - 5:56 pm

ORD

DCA

6h 00m

1 stop

$248JetBlue

Thu, Sep 3 - Sun, Sep 6

8:33 pm - 7:53 am

IAD

ORD

12h 20m

1 stop

8:05 am - 7:38 pm

ORD

IAD

10h 33m

1 stop

$248Frontier

Wed, Jul 8 - Wed, Jul 15

2:40 pm - 5:45 pm

DCA

MDW

4h 05m

1 stop

9:15 am - 12:00 pm

MDW

DCA

1h 45mnonstop

$251Southwest

Mon, Nov 16 - Thu, Nov 19

11:40 am - 5:55 pm

DCA

MDW

7h 15m

2 stops

6:00 am - 8:45 am

MDW

DCA

1h 45mnonstop

$252Southwest

Wed, Jul 22 - Mon, Jul 27

10:27 pm - 11:40 pm

IAD

ORD

2h 13mnonstop

9:39 pm - 12:44 am

ORD

IAD

2h 05mnonstop

$253United Airlines

Fri, Sep 4 - Sun, Sep 6

10:20 pm - 11:31 pm

IAD

ORD

2h 11mnonstop

9:40 pm - 12:45 am

ORD

IAD

2h 05mnonstop

$254United Airlines

Sat, Aug 1 - Mon, Aug 3

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American Airlines flights from Virginia to Chicago

Our best American Airlines deals on Virginia to Chicago flight tickets

American Airlines

Jul 25

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

2h 20m

ORD11:30 pmChicago O'Hare Intl

Jul 27

ORD4:45 pmChicago O'Hare Intl

4h 35m

1 stop

DCA10:20 pmWashington, D.C. Reagan-National

$247

American Airlines

Aug 7

DCA5:00 amWashington, D.C. Reagan-National

5h 00m

1 stop

ORD9:00 amChicago O'Hare Intl

Aug 11

ORD5:55 pmChicago O'Hare Intl

2h 04m

DCA8:59 pmWashington, D.C. Reagan-National

$253

American Airlines

Aug 6

DCA6:59 amWashington, D.C. Reagan-National

4h 31m

1 stop

ORD10:30 amChicago O'Hare Intl

Aug 10

ORD7:03 amChicago O'Hare Intl

1h 57m

DCA10:00 amWashington, D.C. Reagan-National

$255

Delta flights from Virginia to Chicago

Our best Delta deals on Virginia to Chicago flight tickets

Delta

Sep 30

IAD12:31 pmWashington, D.C. Dulles Intl

4h 40m

1 stop

MDW4:11 pmChicago Midway

Oct 7

MDW6:45 pmChicago Midway

3h 17m

1 stop

IAD11:02 pmWashington, D.C. Dulles Intl

$253

Delta

Aug 8

IAD5:16 pmWashington, D.C. Dulles Intl

4h 14m

1 stop

ORD8:30 pmChicago O'Hare Intl

Aug 10

ORD5:20 pmChicago O'Hare Intl

5h 06m

1 stop

IAD11:26 pmWashington, D.C. Dulles Intl

$257

Delta

Jun 30

DCA1:30 pmWashington, D.C. Reagan-National

5h 30m

1 stop

ORD6:00 pmChicago O'Hare Intl

Jul 3

ORD3:22 pmChicago O'Hare Intl

6h 25m

1 stop

DCA10:47 pmWashington, D.C. Reagan-National

$270

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 8/11

5:40 pm-12:15 pm

1 stop19h 35m

Chicago O'Hare Intl

Mon 8/17

10:16 am-6:33 pm

1 stop7h 17m

$246

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 7/25

10:10 pm-11:30 pm

Nonstop2h 20m

Chicago O'Hare Intl

Mon 7/27

4:45 pm-10:20 pm

1 stop4h 35m

$247

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 7/22

7:55 pm-11:15 pm

1 stop4h 20m

Chicago Midway

Mon 7/27

6:00 am-8:45 am

Nonstop1h 45m

$247

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 8/15

8:33 pm-8:02 am

1 stop12h 29m

Chicago O'Hare Intl

Thu 8/20

8:05 am-7:44 pm

1 stop10h 39m

$247

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 9/3

12:50 pm-7:55 pm

1 stop8h 05m

Chicago O'Hare Intl

Sun 9/6

10:56 am-5:56 pm

1 stop6h 00m

$248

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 7/8

8:33 pm-7:53 am

1 stop12h 20m

Chicago O'Hare Intl

Wed 7/15

8:05 am-7:38 pm

1 stop10h 33m

$248

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 11/16

2:40 pm-5:45 pm

1 stop4h 05m

Chicago Midway

Thu 11/19

9:15 am-12:00 pm

Nonstop1h 45m

$251

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 7/22

11:40 am-5:55 pm

2 stops7h 15m

Chicago Midway

Mon 7/27

6:00 am-8:45 am

Nonstop1h 45m

$252

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 9/4

10:27 pm-11:40 pm

Nonstop2h 13m

Chicago O'Hare Intl

Sun 9/6

9:39 pm-12:44 am

Nonstop2h 05m

$253

Quickest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 8/1

10:20 pm-11:31 pm

Nonstop2h 11m

Chicago O'Hare Intl

Mon 8/3

9:40 pm-12:45 am

Nonstop2h 05m

$254

Flights are sorted by cheapest round-trip flights first.

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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 August is, on average, the cheapest month to fly to Chicago from Virginia, with most prices found around $70. If you’re not able to fly to Chicago in August, then December is your next best option. Flight prices from Virginia to Chicago during December average around $73.

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 $458. 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 $636.

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 in the afternoon. Flights from Virginia to Chicago during this time can be as low as $454. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $520.

What is the cheapest Virginia to Chicago flight route?

Fly from Richmond Byrd Intl to Chicago O'Hare Intl 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 $386 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 $298 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 13% 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	$206
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 $206. 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 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 6 operators available for flights from Virginia to Chicago as of June 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 (Enhanced Winglets), making up 19.61% of the total bookings. Other popular models include Embraer 175 with 17.45%, Canadair (Bombardier) Regional Jet CRJ-550 with 14.71%, and Airbus A320-100/200 with 10.38%.

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 2,870 reviews	Search Frontier flights
JetBlue	PriceFrom $126	Free Cancellation	Rating 7.1 3,001 reviews	Search JetBlue flights
Southwest	PriceFrom $178	Free Cancellation	Rating 7.9 4,242 reviews	Search Southwest flights
Delta	PriceFrom $200	Free Cancellation	Rating 7.8 8,424 reviews	Search Delta flights
American Airlines	PriceFrom $203	Free Cancellation	Rating 7.1 11,745 reviews	Search American Airlines flights
United Airlines	PriceFrom $209	Free Cancellation	Rating 7.4 9,875 reviews	Search United Airlines flights

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Portage

Saint Joseph

Lansing

Valparaiso

Schererville

Munster

Crown Point

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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Fly into one of these airports located in Chicago

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Cheap flights from Virginia to Chicago from $99

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 7/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Virginia to Chicago

Our best American Airlines deals on Virginia to Chicago flight tickets

Delta flights from Virginia to Chicago

Our best Delta deals on Virginia to Chicago flight tickets

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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?

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

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

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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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