How does KAYAK find such low prices on flights from Virginia to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Virginia to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Virginia to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Virginia is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Virginia to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Virginia with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Virginia to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Virginia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$89 CHEAP FLIGHTS from Virginia to Chicago

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Flight Deals

Cheap Flights from Virginia to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Virginia to Chicago

Sun, Feb 14 - Tue, Feb 16

1:39 pm - 3:00 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 21mnonstop

6:24 pm - 9:26 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 02mnonstop

$234American Airlines

Sun, Feb 14 - Tue, Feb 16

1:39 pm - 3:00 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 21mnonstop

6:24 pm - 9:26 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 02mnonstop

$234American Airlines

Sat, Nov 21 - Fri, Nov 27

5:10 pm - 6:43 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

2h 33mnonstop

6:20 pm - 9:49 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 29mnonstop

$311United Airlines

Wed, Nov 25 - Fri, Nov 27

6:10 am - 7:50 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

2h 40mnonstop

1:55 pm - 5:07 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 12mnonstop

$311United Airlines

Thu, Nov 12 - Fri, Nov 13

3:53 pm - 8:46 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

17h 53m1 stop Orlando

7:50 pm - 6:41 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

21h 51m2 stops Atlanta Hartsfield-Jackson Tampa

$312Multiple Airlines

Sat, Dec 26 - Sun, Jan 10

7:31 pm - 12:01 amORF Norfolk-MDW Chicago Midway

5h 30m1 stop Atlanta Hartsfield-Jackson

8:30 pm - 5:27 pmMDW Chicago Midway-ORF Norfolk

19h 57m1 stop Orlando

$315Frontier

Tue, Nov 24 - Mon, Nov 30

3:36 pm - 12:43 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

10h 07m1 stop Orlando Sanford Intl

11:53 pm - 1:00 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

36h 07m2 stops San Juan Luis Munoz Marin Intl Orlando

$315Multiple Airlines

Fri, Dec 25 - Mon, Dec 28

7:31 pm - 12:01 amORF Norfolk-MDW Chicago Midway

5h 30m1 stop Atlanta Hartsfield-Jackson

8:35 pm - 4:19 pmMDW Chicago Midway-ORF Norfolk

18h 44m1 stop Orlando

$316Frontier

Fri, Jan 29 - Fri, Jan 29

8:05 am - 9:10 amRIC Richmond Byrd Intl-MDW Chicago Midway

2h 05mnonstop

5:40 pm - 8:40 pmMDW Chicago Midway-RIC Richmond Byrd Intl

2h 00mnonstop

$317Southwest

Tue, Nov 17 - Fri, Nov 20

7:05 am - 8:10 amRIC Richmond Byrd Intl-MDW Chicago Midway

2h 05mnonstop

7:00 pm - 10:00 pmMDW Chicago Midway-RIC Richmond Byrd Intl

2h 00mnonstop

$317Southwest

Recent last minute flight deals from Virginia to Chicago

Tue, Oct 27 - Wed, Oct 28

1:44 pm - 6:45 pmORF Norfolk-ORD Chicago O'Hare Intl

6h 01m1 stop Atlanta Hartsfield-Jackson

9:51 am - 6:44 pmORD Chicago O'Hare Intl-ORF Norfolk

7h 53m1 stop Orlando

$329Frontier

Fri, Oct 30 - Tue, Nov 3

3:44 pm - 8:46 amORF Norfolk-ORD Chicago O'Hare Intl

18h 02m1 stop Orlando

9:51 am - 6:44 pmORD Chicago O'Hare Intl-ORF Norfolk

7h 53m1 stop Orlando

$332Frontier

Thu, Oct 29 - Wed, Nov 4

1:46 pm - 3:00 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 14mnonstop

6:20 pm - 9:19 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

1h 59mnonstop

$334American Airlines

Tue, Oct 27 - Tue, Nov 3

4:49 pm - 6:15 pmROA Roanoke-ORD Chicago O'Hare Intl

2h 26mnonstop

1:29 pm - 4:22 pmORD Chicago O'Hare Intl-ROA Roanoke

1h 53mnonstop

$410American Airlines

Fri, Oct 30 - Fri, Nov 6

2:03 pm - 3:19 pmCHO Charlottesville Albemarle-ORD Chicago O'Hare Intl

2h 16mnonstop

6:55 am - 10:02 amORD Chicago O'Hare Intl-CHO Charlottesville Albemarle

2h 07mnonstop

$414United Airlines

Fri, Oct 30 - Fri, Nov 6

10:45 am - 11:59 amCHO Charlottesville Albemarle-ORD Chicago O'Hare Intl

2h 14mnonstop

5:54 pm - 8:58 pmORD Chicago O'Hare Intl-CHO Charlottesville Albemarle

2h 04mnonstop

$414United Airlines

Wed, Oct 28 - Tue, Nov 3

6:00 am - 9:25 amROA Roanoke-ORD Chicago O'Hare Intl

4h 25m1 stop Atlanta Hartsfield-Jackson

2:30 pm - 10:49 pmORD Chicago O'Hare Intl-ROA Roanoke

7h 19m1 stop New York LaGuardia

$434Delta

Thu, Oct 29 - Tue, Nov 3

6:00 am - 12:13 pmROA Roanoke-ORD Chicago O'Hare Intl

7h 13m1 stop Atlanta Hartsfield-Jackson

2:30 pm - 10:49 pmORD Chicago O'Hare Intl-ROA Roanoke

7h 19m1 stop New York LaGuardia

$434Delta

Tue, Oct 27 - Fri, Oct 30

1:44 pm - 6:45 pmORF Norfolk-ORD Chicago O'Hare Intl

6h 01m1 stop Atlanta Hartsfield-Jackson

7:00 am - 8:59 pmORD Chicago O'Hare Intl-ORF Norfolk

12h 59m1 stop Fort Lauderdale

$436Multiple Airlines

Tue, Oct 27 - Fri, Oct 30

1:44 pm - 6:45 pmORF Norfolk-ORD Chicago O'Hare Intl

6h 01m1 stop Atlanta Hartsfield-Jackson

7:00 am - 8:59 pmORD Chicago O'Hare Intl-ORF Norfolk

12h 59m1 stop Fort Lauderdale

$436Multiple Airlines

Recent direct flight deals from Virginia to Chicago

Sun, Feb 14 - Tue, Feb 16

1:39 pm - 3:00 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 21mnonstop

6:24 pm - 9:26 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 02mnonstop

$234American Airlines

Sun, Feb 14 - Tue, Feb 16

1:39 pm - 3:00 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 21mnonstop

6:24 pm - 9:26 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 02mnonstop

$234American Airlines

Thu, Dec 3 - Sat, Dec 5

1:41 pm - 3:00 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 19mnonstop

6:50 pm - 9:59 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 09mnonstop

$234American Airlines

Thu, Nov 12 - Sat, Nov 14

1:43 pm - 3:00 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 17mnonstop

6:20 pm - 9:19 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

1h 59mnonstop

$234American Airlines

Sat, Nov 21 - Fri, Nov 27

5:10 pm - 6:43 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

2h 33mnonstop

6:20 pm - 9:49 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 29mnonstop

$311United Airlines

Wed, Nov 25 - Fri, Nov 27

6:10 am - 7:50 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

2h 40mnonstop

1:55 pm - 5:07 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 12mnonstop

$311United Airlines

Wed, Nov 25 - Fri, Nov 27

6:10 am - 7:50 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

2h 40mnonstop

6:20 pm - 9:49 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 29mnonstop

$311United Airlines

Tue, Nov 17 - Fri, Nov 20

7:05 am - 8:10 amRIC Richmond Byrd Intl-MDW Chicago Midway

2h 05mnonstop

7:00 pm - 10:00 pmMDW Chicago Midway-RIC Richmond Byrd Intl

2h 00mnonstop

$317Southwest

Fri, Jan 29 - Fri, Jan 29

8:05 am - 9:10 amRIC Richmond Byrd Intl-MDW Chicago Midway

2h 05mnonstop

5:40 pm - 8:40 pmMDW Chicago Midway-RIC Richmond Byrd Intl

2h 00mnonstop

$317Southwest

Thu, Dec 10 - Mon, Dec 14

8:00 am - 9:15 amORF Norfolk-MDW Chicago Midway

2h 15mnonstop

6:25 pm - 9:30 pmMDW Chicago Midway-ORF Norfolk

2h 05mnonstop

$323Southwest

Useful Info

Low season	January
High season	July
Cheapest flight	$89

Best time to beat the crowds with an average 22% drop in price.

Most popular time to fly with an average 5% increase in price.

Flight from Richmond to Chicago O'Hare Airport

How does KAYAK find such low prices on flights from Virginia to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Virginia to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Virginia to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Virginia is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Virginia to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Virginia with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Virginia to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Virginia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

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$89 Find Cheap Flights from Virginia to Chicago - Compare and Save

Cheap Flights from Virginia to Chicago

Recent round-trip flight deals from Virginia to Chicago

Recent one-way flight deals from Virginia to Chicago

Recent last minute flight deals from Virginia to Chicago

Recent direct flight deals from Virginia to Chicago

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from Virginia to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Virginia

Find direct flights for Chicago

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight