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

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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

Fri, Nov 6 - Sun, Nov 8

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

Thu, Oct 29 - Mon, Nov 2

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

$234American Airlines

Mon, Oct 26 - Wed, Oct 28

6:15 pm - 10:00 pmRIC Richmond Byrd Intl-MDW Chicago Midway

4h 45m1 stop Baltimore/Washington

7:40 am - 2:35 pmMDW Chicago Midway-RIC Richmond Byrd Intl

5h 55m1 stop Nashville Intl

$310Southwest

Fri, Dec 4 - Sun, Dec 6

1:59 pm - 8:48 pmRIC Richmond Byrd Intl-MDW Chicago Midway

7h 49m1 stop Orlando

9:37 pm - 1:04 pmMDW Chicago Midway-RIC Richmond Byrd Intl

14h 27m1 stop Orlando

$310Frontier

Fri, Dec 4 - Sun, Dec 6

1:59 pm - 9:18 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

20h 19m1 stop Orlando

5:24 pm - 1:04 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

18h 40m1 stop Orlando

$310Frontier

Sat, Oct 31 - Tue, Nov 3

6:20 am - 1:15 pmRIC Richmond Byrd Intl-MDW Chicago Midway

7h 55m2 stops Baltimore/Washington Lambert-St Louis

6:00 am - 11:40 amMDW Chicago Midway-RIC Richmond Byrd Intl

4h 40m1 stop Baltimore/Washington

$313Southwest

Fri, Nov 13 - Mon, Nov 16

7:46 pm - 11:54 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

5h 08m1 stop Atlanta Hartsfield-Jackson

10:06 am - 5:02 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

5h 56m1 stop New York LaGuardia

$317Delta

Mon, Dec 14 - Wed, Jan 27

7:21 pm - 11:33 amORF Norfolk-MDW Chicago Midway

17h 12m1 stop Atlanta Hartsfield-Jackson

1:18 pm - 4:30 pmMDW Chicago Midway-ORF Norfolk

26h 12m2 stops Atlanta Hartsfield-Jackson New Orleans Louis Armstrong

$317Multiple Airlines

Tue, Dec 15 - Wed, Jan 27

12:44 pm - 7:20 amORF Norfolk-ORD Chicago O'Hare Intl

19h 36m2 stops Jacksonville Atlanta Hartsfield-Jackson

10:18 am - 10:29 pmORD Chicago O'Hare Intl-ORF Norfolk

11h 11m1 stop Tampa

$318Multiple Airlines

Tue, Nov 10 - Fri, Nov 13

8:05 am - 2:49 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

7h 44m1 stop Atlanta Hartsfield-Jackson

6:15 pm - 12:40 amORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

5h 25m1 stop Atlanta Hartsfield-Jackson

$328Delta

Recent last minute flight deals from Virginia to Chicago

Fri, Oct 9 - Mon, Oct 12

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

2h 14mnonstop

6:20 pm - 9:26 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 06mnonstop

$334American Airlines

Sat, Oct 10 - Mon, Oct 12

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

2h 14mnonstop

6:20 pm - 9:26 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 06mnonstop

$334American Airlines

Thu, Oct 8 - Sat, Oct 10

1:39 pm - 5:45 pmORF Norfolk-MDW Chicago Midway

5h 06m1 stop Atlanta Hartsfield-Jackson

6:21 am - 2:55 pmMDW Chicago Midway-ORF Norfolk

7h 34m1 stop Atlanta Hartsfield-Jackson

$337Frontier

Thu, Oct 8 - Sat, Oct 10

1:39 pm - 6:31 pmORF Norfolk-ORD Chicago O'Hare Intl

5h 52m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:55 pmORD Chicago O'Hare Intl-ORF Norfolk

7h 55m1 stop Atlanta Hartsfield-Jackson

$343Frontier

Tue, Oct 13 - Tue, Oct 27

10:18 am - 11:34 amLYH Lynchburg Preston-Glenn Field-ORD Chicago O'Hare Intl

2h 16mnonstop

9:20 pm - 12:18 amORD Chicago O'Hare Intl-LYH Lynchburg Preston-Glenn Field

1h 58mnonstop

$417United Airlines

Fri, Oct 9 - Fri, Oct 9

1:00 pm - 2:34 pmORF Norfolk-ORD Chicago O'Hare Intl

2h 34mnonstop

5:45 pm - 9:42 amORD Chicago O'Hare Intl-ORF Norfolk

14h 57m2 stops Lynchburg Preston-Glenn Field Washington, D.C. Dulles Intl

$449United Airlines

Tue, Oct 13 - Mon, Oct 19

7:41 pm - 7:51 amORF Norfolk-ORD Chicago O'Hare Intl

13h 10m1 stop Orlando

8:04 am - 12:04 pmORD Chicago O'Hare Intl-ORF Norfolk

27h 00m2 stops Fort Lauderdale Jacksonville

$456Multiple Airlines

Tue, Oct 13 - Mon, Oct 19

1:19 pm - 11:43 pmORF Norfolk-MDW Chicago Midway

11h 24m1 stop Atlanta Hartsfield-Jackson

6:15 am - 12:18 amMDW Chicago Midway-ORF Norfolk

17h 03m2 stops Atlanta Hartsfield-Jackson Jacksonville

$466Multiple Airlines

Sat, Oct 10 - Tue, Oct 13

5:33 pm - 11:57 pmCHO Charlottesville Albemarle-ORD Chicago O'Hare Intl

7h 24m1 stop Atlanta Hartsfield-Jackson

6:30 am - 1:50 pmORD Chicago O'Hare Intl-CHO Charlottesville Albemarle

6h 20m1 stop Atlanta Hartsfield-Jackson

$495Delta

Thu, Oct 8 - Sun, Oct 11

11:59 am - 4:58 pmCHO Charlottesville Albemarle-ORD Chicago O'Hare Intl

5h 59m1 stop Atlanta Hartsfield-Jackson

5:27 am - 11:14 amORD Chicago O'Hare Intl-CHO Charlottesville Albemarle

4h 47m1 stop Atlanta Hartsfield-Jackson

$509Delta

Recent direct flight deals from Virginia to Chicago

Fri, Nov 6 - Sun, Nov 8

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

Thu, Oct 29 - Mon, Nov 2

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

$234American Airlines

Fri, Nov 13 - Sun, Nov 15

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

Wed, Nov 4 - Mon, Nov 9

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

Fri, Oct 30 - Tue, Nov 3

7:35 pm - 8:35 pmRIC Richmond Byrd Intl-MDW Chicago Midway

2h 00mnonstop

1:15 pm - 4:00 pmMDW Chicago Midway-RIC Richmond Byrd Intl

1h 45mnonstop

$316Southwest

Fri, Jan 8 - Mon, Jan 11

7:50 am - 9:05 amRIC Richmond Byrd Intl-MDW Chicago Midway

2h 15mnonstop

1:45 pm - 4:35 pmMDW Chicago Midway-RIC Richmond Byrd Intl

1h 50mnonstop

$317Southwest

Fri, Oct 30 - Sun, Nov 1

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

2h 16mnonstop

10:25 am - 1:28 pmORD Chicago O'Hare Intl-CHO Charlottesville Albemarle

2h 03mnonstop

$319United Airlines

Fri, Dec 4 - Sun, Dec 6

2:04 pm - 3:15 pmCHO Charlottesville Albemarle-ORD Chicago O'Hare Intl

2h 11mnonstop

10:25 am - 1:29 pmORD Chicago O'Hare Intl-CHO Charlottesville Albemarle

2h 04mnonstop

$319United Airlines

Wed, Nov 4 - Sat, Nov 7

5:49 pm - 7:00 pmCHO Charlottesville Albemarle-ORD Chicago O'Hare Intl

2h 11mnonstop

6:55 am - 10:00 amORD Chicago O'Hare Intl-CHO Charlottesville Albemarle

2h 05mnonstop

$319United Airlines

Wed, Oct 28 - Fri, Oct 30

7:55 am - 8:50 amRIC Richmond Byrd Intl-MDW Chicago Midway

1h 55mnonstop

12:45 pm - 3:40 pmMDW Chicago Midway-RIC Richmond Byrd Intl

1h 55mnonstop

$331Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$89

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

Most popular time to fly with an average 3% increase in price.

Flight from Norfolk 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

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

More options for your flight to Chicago

Add a hotel or car rental

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

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

Car rentals in Chicago

$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