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.

$100 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

Thu, Nov 12 - Tue, Nov 17

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

2h 17mnonstop

6:50 pm - 9:49 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

1h 59mnonstop

$234American Airlines

Mon, Jan 18 - Sat, Jan 23

2:10 pm - 3:30 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 20mnonstop

6:29 pm - 9:33 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 04mnonstop

$234American Airlines

Mon, Dec 7 - Wed, Dec 9

4:40 pm - 9:25 pmRIC Richmond Byrd Intl-MDW Chicago Midway

5h 45m1 stop Baltimore/Washington

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

1h 45mnonstop

$307Southwest

Tue, Jan 5 - Sat, Jan 9

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

2h 05mnonstop

4:55 pm - 10:20 pmMDW Chicago Midway-RIC Richmond Byrd Intl

4h 25m1 stop Baltimore/Washington

$307Southwest

Mon, Nov 23 - Fri, Nov 27

6:00 am - 10:48 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

5h 48m1 stop Newark

10:59 am - 2:16 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 17mnonstop

$307United Airlines

Mon, Nov 9 - Wed, Nov 11

5:48 pm - 10:18 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

5h 30m1 stop Newark

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

2h 29mnonstop

$307United Airlines

Tue, Nov 10 - Tue, Nov 17

1:44 pm - 6:30 pmORF Norfolk-ORD Chicago O'Hare Intl

5h 46m1 stop Atlanta Hartsfield-Jackson

7:35 pm - 6:44 pmORD Chicago O'Hare Intl-ORF Norfolk

22h 09m2 stops Atlanta Hartsfield-Jackson Orlando

$309Frontier

Mon, Nov 16 - Mon, Nov 16

5:30 am - 10:24 amORF Norfolk-MDW Chicago Midway

5h 54m1 stop Atlanta Hartsfield-Jackson

6:44 pm - 11:44 pmMDW Chicago Midway-ORF Norfolk

4h 00m1 stop Detroit Metropolitan Wayne County

$309Delta

Fri, Jan 8 - Sun, Jan 10

12:57 pm - 12:55 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

12h 58m1 stop Orlando

5:16 pm - 12:02 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

17h 46m1 stop Orlando

$310Frontier

Fri, Nov 27 - Sat, Dec 5

6:00 am - 10:24 amRIC Richmond Byrd Intl-MDW Chicago Midway

5h 24m1 stop Atlanta Hartsfield-Jackson

6:41 pm - 11:47 pmMDW Chicago Midway-RIC Richmond Byrd Intl

4h 06m1 stop Detroit Metropolitan Wayne County

$317Delta

Recent last minute flight deals from Virginia to Chicago

Sat, Oct 17 - Wed, Nov 18

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

$309American Airlines

Fri, Oct 16 - Wed, Nov 18

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

$309American Airlines

Sat, Oct 17 - Tue, Oct 20

7:41 pm - 7:31 amORF Norfolk-ORD Chicago O'Hare Intl

12h 50m1 stop Orlando

6:00 am - 12:34 pmORD Chicago O'Hare Intl-ORF Norfolk

5h 34m1 stop Atlanta Hartsfield-Jackson

$395Frontier

Sun, Oct 18 - Tue, Oct 20

7:41 pm - 7:31 amORF Norfolk-ORD Chicago O'Hare Intl

12h 50m1 stop Orlando

6:00 am - 12:34 pmORD Chicago O'Hare Intl-ORF Norfolk

5h 34m1 stop Atlanta Hartsfield-Jackson

$403Frontier

Sun, Oct 18 - Sat, Oct 31

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

Sat, Oct 17 - Mon, Oct 19

9:19 am - 4:23 pmROA Roanoke-ORD Chicago O'Hare Intl

8h 04m1 stop New York LaGuardia

6:08 pm - 12:27 amORD Chicago O'Hare Intl-ROA Roanoke

5h 19m1 stop Atlanta Hartsfield-Jackson

$449Delta

Sat, Oct 17 - Sun, Oct 18

5:51 pm - 7:00 pmROA Roanoke-ORD Chicago O'Hare Intl

2h 09mnonstop

7:45 pm - 10:59 pmORD Chicago O'Hare Intl-ROA Roanoke

2h 14mnonstop

$453United Airlines

Sat, Oct 17 - Mon, Oct 19

9:19 am - 8:30 pmROA Roanoke-ORD Chicago O'Hare Intl

12h 11m2 stops New York LaGuardia Detroit Metropolitan Wayne County

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

7h 19m1 stop New York LaGuardia

$454Delta

Sun, Oct 18 - Sun, Oct 25

7:41 pm - 7:31 amORF Norfolk-ORD Chicago O'Hare Intl

12h 50m1 stop Orlando

8:04 am - 12:18 amORD Chicago O'Hare Intl-ORF Norfolk

39h 14m2 stops Fort Lauderdale Jacksonville

$497Multiple Airlines

Thu, Oct 15 - Tue, Oct 20

3:50 pm - 7:31 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

16h 41m1 stop Orlando

8:04 am - 6:41 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

33h 37m2 stops Fort Lauderdale Tampa

$504Multiple Airlines

Recent direct flight deals from Virginia to Chicago

Thu, Nov 12 - Tue, Nov 17

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

2h 17mnonstop

6:50 pm - 9:49 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

1h 59mnonstop

$234American Airlines

Tue, Nov 10 - Tue, Nov 17

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

2h 17mnonstop

6:50 pm - 9:49 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

1h 59mnonstop

$234American Airlines

Fri, Dec 11 - Mon, Dec 14

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 5 - Sat, Nov 7

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, Jan 15 - Mon, Jan 18

1:35 pm - 2:50 pmRIC Richmond Byrd Intl-MDW Chicago Midway

2h 15mnonstop

6:05 pm - 9:00 pmMDW Chicago Midway-RIC Richmond Byrd Intl

1h 55mnonstop

$308Southwest

Thu, Nov 5 - Mon, Nov 9

7:30 am - 8:45 amORF Norfolk-MDW Chicago Midway

2h 15mnonstop

7:05 pm - 10:10 pmMDW Chicago Midway-ORF Norfolk

2h 05mnonstop

$317Southwest

Tue, Nov 3 - Sat, Nov 7

3:46 pm - 5:30 pmORF Norfolk-ORD Chicago O'Hare Intl

2h 44mnonstop

7:29 am - 10:53 amORD Chicago O'Hare Intl-ORF Norfolk

2h 24mnonstop

$317United Airlines

Tue, Nov 10 - Tue, Nov 17

3:46 pm - 5:30 pmORF Norfolk-ORD Chicago O'Hare Intl

2h 44mnonstop

7:29 am - 10:53 amORD Chicago O'Hare Intl-ORF Norfolk

2h 24mnonstop

$317United Airlines

Mon, Dec 21 - Fri, Dec 25

7:20 pm - 8:35 pmORF Norfolk-MDW Chicago Midway

2h 15mnonstop

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

2h 00mnonstop

$317Southwest

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

Useful Info

Low season	January
High season	July
Cheapest flight	$100

Best time to beat the crowds with an average 23% drop in price.

Most popular time to fly with an average 7% 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

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

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$100 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