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

Tue, Dec 22 - Fri, Dec 25

1:13 pm - 2:32 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 19mnonstop

6:59 pm - 10:08 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 09mnonstop

$234American Airlines

Thu, Dec 3 - Thu, Dec 10

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, Dec 10 - Mon, Dec 14

6:05 pm - 9:30 pmORF Norfolk-MDW Chicago Midway

4h 25m1 stop Baltimore/Washington

1:20 pm - 9:15 pmMDW Chicago Midway-ORF Norfolk

6h 55m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington

$309Southwest

Thu, Dec 10 - Fri, Dec 11

6:05 pm - 9:30 pmORF Norfolk-MDW Chicago Midway

4h 25m1 stop Baltimore/Washington

7:50 am - 5:15 pmMDW Chicago Midway-ORF Norfolk

8h 25m2 stops Buffalo Baltimore/Washington

$309Southwest

Thu, Dec 10 - Mon, Dec 14

5:09 pm - 1:08 amORF Norfolk-ORD Chicago O'Hare Intl

8h 59m1 stop Orlando

5:35 am - 4:14 pmORD Chicago O'Hare Intl-ORF Norfolk

9h 39m1 stop Orlando

$309Frontier

Sun, Nov 15 - Sun, Nov 22

1:31 pm - 11:47 pmORF Norfolk-MDW Chicago Midway

11h 16m1 stop Atlanta Hartsfield-Jackson

8:42 pm - 3:56 pmMDW Chicago Midway-ORF Norfolk

18h 14m1 stop Orlando

$310Frontier

Fri, Dec 11 - Mon, Dec 14

5:25 pm - 10:54 pmORF Norfolk-MDW Chicago Midway

6h 29m1 stop Atlanta Hartsfield-Jackson

6:41 pm - 11:43 pmMDW Chicago Midway-ORF Norfolk

4h 02m1 stop Detroit Metropolitan Wayne County

$311Delta

Wed, Dec 30 - Mon, Jan 11

7:31 pm - 12:00 pmORF Norfolk-ORD Chicago O'Hare Intl

17h 29m1 stop Atlanta Hartsfield-Jackson

7:10 am - 11:34 amORD Chicago O'Hare Intl-ORF Norfolk

27h 24m2 stops Fort Lauderdale Jacksonville

$311Multiple Airlines

Thu, Feb 18 - Sat, Feb 20

6:15 am - 7:51 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

2h 36mnonstop

1:55 pm - 5:16 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 21mnonstop

$317United Airlines

Wed, Jan 6 - Fri, Jan 8

8:05 am - 1:09 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

6h 04m1 stop Newark

8:40 am - 1:45 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

4h 05m1 stop Washington, D.C. Dulles Intl

$317United Airlines

Recent last minute flight deals from Virginia to Chicago

Sun, Nov 8 - Tue, Nov 10

1:31 pm - 6:45 pmORF Norfolk-ORD Chicago O'Hare Intl

6h 14m1 stop Atlanta Hartsfield-Jackson

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

7h 53m1 stop Orlando

$320Frontier

Sun, Nov 8 - Wed, Nov 11

1:31 pm - 6:45 pmORF Norfolk-ORD Chicago O'Hare Intl

6h 14m1 stop Atlanta Hartsfield-Jackson

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

7h 53m1 stop Orlando

$320Frontier

Sat, Nov 7 - 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

$334American Airlines

Sun, Nov 8 - Wed, Jan 6

5:06 pm - 11:40 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

19h 34m2 stops Nashville Intl Quincy Regional

7:52 pm - 8:13 amORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

11h 21m1 stop Tampa

$375Multiple Airlines

Sun, Nov 8 - Tue, Jan 5

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

17h 53m1 stop Orlando

9:40 am - 8:13 amORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

45h 33m2 stops Atlanta Hartsfield-Jackson Tampa

$381Multiple Airlines

Thu, Nov 5 - Fri, Jan 8

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

2h 40mnonstop

6:15 pm - 9:26 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 11mnonstop

$389United Airlines

Thu, Nov 5 - Fri, Jan 8

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

2h 40mnonstop

12:40 pm - 6:45 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

5h 05m1 stop Newark

$399United Airlines

Thu, Nov 5 - Fri, Jan 8

8:25 pm - 11:15 pmRIC Richmond Byrd Intl-MDW Chicago Midway

3h 50m1 stop Baltimore/Washington

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

2h 00mnonstop

$399Southwest

Wed, Nov 4 - Tue, Jan 19

4:52 pm - 6:20 pmROA Roanoke-ORD Chicago O'Hare Intl

2h 28mnonstop

1:42 pm - 4:39 pmORD Chicago O'Hare Intl-ROA Roanoke

1h 57mnonstop

$400American Airlines

Thu, Nov 5 - Fri, Jan 8

8:25 pm - 11:15 pmRIC Richmond Byrd Intl-MDW Chicago Midway

3h 50m1 stop Baltimore/Washington

10:40 am - 3:40 pmMDW Chicago Midway-RIC Richmond Byrd Intl

4h 00m1 stop Nashville Intl

$409Southwest

Recent direct flight deals from Virginia to Chicago

Tue, Dec 22 - Fri, Dec 25

1:13 pm - 2:32 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 19mnonstop

6:59 pm - 10:08 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 09mnonstop

$234American Airlines

Thu, Dec 3 - Thu, Dec 10

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

Fri, Dec 4 - Sun, Dec 6

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

Sat, Jan 23 - Thu, Jan 28

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

2h 20mnonstop

6:20 pm - 9:24 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 04mnonstop

$234American Airlines

Thu, Feb 18 - Sat, Feb 20

6:15 am - 7:51 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

2h 36mnonstop

1:55 pm - 5:16 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 21mnonstop

$317United Airlines

Thu, Nov 19 - Mon, Nov 23

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

Tue, Jan 5 - Tue, Jan 12

7:05 am - 8:10 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, Feb 18 - Sat, Feb 20

8:00 am - 9:05 amRIC Richmond Byrd Intl-MDW Chicago Midway

2h 05mnonstop

2:20 pm - 5:15 pmMDW Chicago Midway-RIC Richmond Byrd Intl

1h 55mnonstop

$317Southwest

Fri, Nov 27 - Mon, Nov 30

10:02 am - 11:19 amLYH Lynchburg Preston-Glenn Field-ORD Chicago O'Hare Intl

2h 17mnonstop

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

1h 58mnonstop

$327United Airlines

Sat, Mar 6 - Tue, Mar 16

10:24 am - 11:42 amLYH Lynchburg Preston-Glenn Field-ORD Chicago O'Hare Intl

2h 18mnonstop

9:25 pm - 12:26 amORD Chicago O'Hare Intl-LYH Lynchburg Preston-Glenn Field

2h 01mnonstop

$327United Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$100

Best time to beat the crowds with an average 12% drop in price.

Most popular time to fly with an average 4% 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

Chesterton

Schererville

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