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, Dec 3 - 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

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 11 - Mon, Dec 14

7:26 pm - 4:33 pmORF Norfolk-ORD Chicago O'Hare Intl

22h 07m2 stops Atlanta Hartsfield-Jackson Dallas/Fort Worth

8:30 am - 6:31 pmORD Chicago O'Hare Intl-ORF Norfolk

9h 01m1 stop Atlanta Hartsfield-Jackson

$302Frontier

Thu, Dec 3 - Thu, Dec 10

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

2h 15mnonstop

8:50 am - 1:30 pmMDW Chicago Midway-ORF Norfolk

3h 40m1 stop Baltimore/Washington

$303Southwest

Thu, Feb 25 - Sat, Feb 27

5:14 pm - 3:56 pmORF Norfolk-ORD Chicago O'Hare Intl

23h 42m1 stop Orlando

5:16 pm - 4:19 pmORD Chicago O'Hare Intl-ORF Norfolk

22h 03m1 stop Orlando

$304Frontier

Thu, Dec 3 - Sat, Dec 5

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

2h 15mnonstop

4:25 pm - 9:15 pmMDW Chicago Midway-ORF Norfolk

3h 50m1 stop Baltimore/Washington

$307Southwest

Thu, Dec 3 - Sat, Dec 5

6:00 am - 11:47 amORF Norfolk-ORD Chicago O'Hare Intl

6h 47m1 stop Newark

11:59 am - 3:21 pmORD Chicago O'Hare Intl-ORF Norfolk

2h 22mnonstop

$307United Airlines

Sat, Dec 19 - Wed, Dec 23

7:49 pm - 12:01 amORF Norfolk-ORD Chicago O'Hare Intl

5h 12m1 stop Washington, D.C. Dulles Intl

5:55 pm - 9:24 pmORD Chicago O'Hare Intl-ORF Norfolk

2h 29mnonstop

$307United Airlines

Sat, Dec 5 - Sun, Dec 6

7:00 am - 10:00 pmORF Norfolk-ORD Chicago O'Hare Intl

16h 00m2 stops Tampa Atlanta Hartsfield-Jackson

10:29 pm - 6:31 pmORD Chicago O'Hare Intl-ORF Norfolk

19h 02m1 stop Atlanta Hartsfield-Jackson

$312Multiple Airlines

Sat, Dec 5 - Sat, Dec 12

7:16 pm - 4:06 pmORF Norfolk-MDW Chicago Midway

21h 50m1 stop Atlanta Hartsfield-Jackson

12:28 pm - 8:45 pmMDW Chicago Midway-ORF Norfolk

31h 17m2 stops Atlanta Hartsfield-Jackson Columbus

$313Multiple Airlines

Recent last minute flight deals from Virginia to Chicago

Thu, Nov 12 - 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

$334American Airlines

Fri, Nov 13 - Thu, Nov 19

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

2h 17mnonstop

6:27 pm - 9:32 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 05mnonstop

$334American Airlines

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

$339Frontier

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

$339Frontier

Mon, Nov 9 - Fri, Nov 13

3:44 pm - 5:07 pmORF Norfolk-ORD Chicago O'Hare Intl

26h 23m1 stop Orlando

7:55 am - 6:03 pmORD Chicago O'Hare Intl-ORF Norfolk

33h 08m2 stops Fort Lauderdale Jacksonville

$378Multiple Airlines

Fri, Nov 13 - Mon, Nov 16

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

18h 02m1 stop Orlando

2:59 pm - 8:59 pmORD Chicago O'Hare Intl-ORF Norfolk

29h 00m1 stop Fort Lauderdale

$383Multiple Airlines

Tue, Nov 10 - Tue, Nov 17

2:01 pm - 3:10 pmROA Roanoke-ORD Chicago O'Hare Intl

2h 09mnonstop

6:05 pm - 11:44 pmORD Chicago O'Hare Intl-ROA Roanoke

4h 39m1 stop Washington, D.C. Dulles Intl

$424United Airlines

Tue, Nov 10 - Tue, Nov 17

10:26 am - 2:38 pmROA Roanoke-ORD Chicago O'Hare Intl

5h 12m1 stop Washington, D.C. Dulles Intl

8:50 am - 2:15 pmORD Chicago O'Hare Intl-ROA Roanoke

4h 25m1 stop Washington, D.C. Dulles Intl

$434United Airlines

Fri, Nov 13 - Sun, Nov 15

8:10 am - 9:15 amRIC Richmond Byrd Intl-MDW Chicago Midway

2h 05mnonstop

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

2h 00mnonstop

$471Southwest

Fri, Nov 13 - Fri, Nov 13

8:10 am - 9:15 amRIC Richmond Byrd Intl-MDW Chicago Midway

2h 05mnonstop

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

2h 00mnonstop

$471Southwest

Recent direct flight deals from Virginia to Chicago

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

Tue, Dec 22 - Fri, Jan 1

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

Fri, Dec 4 - Fri, Dec 11

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

Wed, Jan 6 - Sat, Jan 9

10:10 am - 11:42 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

2h 32mnonstop

2:00 pm - 5:19 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 19mnonstop

$319United Airlines

Wed, Jan 6 - Sat, Jan 9

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

2h 05mnonstop

7:40 am - 10:40 amMDW Chicago Midway-RIC Richmond Byrd Intl

2h 00mnonstop

$319Southwest

Wed, Dec 9 - Fri, Dec 11

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

2h 15mnonstop

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

2h 05mnonstop

$323Southwest

Thu, Dec 3 - Thu, Dec 10

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

Sat, Dec 5 - Sat, Dec 12

10:25 am - 11:43 amLYH Lynchburg Preston-Glenn Field-ORD Chicago O'Hare Intl

2h 18mnonstop

9:30 pm - 12:28 amORD Chicago O'Hare Intl-LYH Lynchburg Preston-Glenn Field

1h 58mnonstop

$327United Airlines

Sat, Dec 12 - Mon, Jan 18

10:25 am - 11:43 amLYH Lynchburg Preston-Glenn Field-ORD Chicago O'Hare Intl

2h 18mnonstop

9:25 pm - 12:29 amORD Chicago O'Hare Intl-LYH Lynchburg Preston-Glenn Field

2h 04mnonstop

$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 Midway 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