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

Wed, Dec 2 - Mon, Dec 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

Thu, Oct 15 - Sun, Oct 18

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

$234American Airlines

Fri, Nov 6 - Mon, Nov 9

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

$287United Airlines

Fri, Nov 6 - Mon, Nov 9

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

$287United Airlines

Sat, Dec 12 - Mon, Dec 14

4:00 pm - 7:40 pmRIC Richmond Byrd Intl-MDW Chicago Midway

4h 40m1 stop Baltimore/Washington

1:20 pm - 9:15 pmMDW Chicago Midway-RIC Richmond Byrd Intl

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

$303Southwest

Sat, Jan 16 - Mon, Jan 18

9:45 am - 4:25 pmRIC Richmond Byrd Intl-MDW Chicago Midway

7h 40m1 stop Atlanta Hartsfield-Jackson

5:59 pm - 11:16 pmMDW Chicago Midway-RIC Richmond Byrd Intl

4h 17m1 stop Detroit Metropolitan Wayne County

$304Delta

Fri, Dec 11 - Sun, Dec 13

1:59 pm - 8:42 pmRIC Richmond Byrd Intl-MDW Chicago Midway

7h 43m1 stop Orlando

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

14h 27m1 stop Orlando

$305Frontier

Sat, Oct 24 - Mon, Oct 26

8:35 am - 9:35 amRIC Richmond Byrd Intl-MDW Chicago Midway

2h 00mnonstop

5:00 am - 10:25 amMDW Chicago Midway-RIC Richmond Byrd Intl

4h 25m1 stop Baltimore/Washington

$307Southwest

Thu, Nov 19 - Sun, Nov 22

3:51 pm - 3:52 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

25h 01m1 stop Orlando

5:12 pm - 2:26 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

20h 14m1 stop Orlando

$310Frontier

Thu, Oct 15 - Mon, Oct 19

5:00 pm - 8:30 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

4h 30m1 stop Detroit Metropolitan Wayne County

2:30 pm - 10:09 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

6h 39m1 stop New York LaGuardia

$317Delta

Recent last minute flight deals from Virginia to Chicago

Fri, Sep 25 - Sun, Sep 27

1:05 pm - 2:19 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 14mnonstop

6:14 pm - 9:21 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 07mnonstop

$334American Airlines

Mon, Sep 28 - Thu, Oct 1

5:51 pm - 10:59 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

6h 08m1 stop Orlando

3:50 pm - 4:56 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

24h 06m1 stop Orlando

$396Frontier

Fri, Sep 25 - Sun, Sep 27

5:51 pm - 10:59 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

6h 08m1 stop Orlando

3:50 pm - 4:56 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

24h 06m1 stop Orlando

$396Frontier

Fri, Sep 25 - Sat, Sep 26

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

2h 09mnonstop

6:55 am - 9:57 amORD Chicago O'Hare Intl-ROA Roanoke

2h 02mnonstop

$429United Airlines

Fri, Sep 25 - Sat, Sep 26

5:47 pm - 7:14 pmROA Roanoke-ORD Chicago O'Hare Intl

2h 27mnonstop

2:13 pm - 5:17 pmORD Chicago O'Hare Intl-ROA Roanoke

2h 04mnonstop

$429American Airlines

Sat, Sep 26 - Sat, Sep 26

6:45 am - 7:52 amCHO Charlottesville Albemarle-ORD Chicago O'Hare Intl

2h 07mnonstop

10:25 am - 9:51 amORD Chicago O'Hare Intl-CHO Charlottesville Albemarle

22h 26m2 stops Harrisburg Washington, D.C. Dulles Intl

$449United Airlines

Fri, Sep 25 - Sat, Sep 26

11:12 am - 4:37 pmROA Roanoke-ORD Chicago O'Hare Intl

6h 25m1 stop Atlanta Hartsfield-Jackson

8:55 am - 9:51 pmORD Chicago O'Hare Intl-ROA Roanoke

11h 56m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

$454Delta

Wed, Sep 23 - Sat, Sep 26

6:40 pm - 11:59 pmROA Roanoke-ORD Chicago O'Hare Intl

6h 19m1 stop Atlanta Hartsfield-Jackson

1:51 pm - 9:51 pmORD Chicago O'Hare Intl-ROA Roanoke

7h 00m1 stop Atlanta Hartsfield-Jackson

$473Delta

Thu, Sep 24 - Sat, Sep 26

1:18 pm - 5:46 pmORF Norfolk-MDW Chicago Midway

5h 28m1 stop Atlanta Hartsfield-Jackson

6:25 am - 10:29 pmMDW Chicago Midway-ORF Norfolk

15h 04m2 stops Atlanta Hartsfield-Jackson Tampa

$508Multiple Airlines

Thu, Sep 24 - Sat, Sep 26

1:18 pm - 5:46 pmORF Norfolk-MDW Chicago Midway

5h 28m1 stop Atlanta Hartsfield-Jackson

6:25 am - 10:29 pmMDW Chicago Midway-ORF Norfolk

15h 04m2 stops Atlanta Hartsfield-Jackson Tampa

$519Multiple Airlines

Recent direct flight deals from Virginia to Chicago

Wed, Dec 2 - Mon, Dec 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

Thu, Oct 15 - Sun, Oct 18

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

$234American Airlines

Thu, Oct 29 - Sat, Oct 31

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

$234American Airlines

Thu, Nov 5 - 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

Fri, Nov 6 - Mon, Nov 9

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

$287United Airlines

Fri, Nov 6 - Mon, Nov 9

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

$287United Airlines

Thu, Oct 22 - Sun, Oct 25

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

$287United Airlines

Thu, Dec 17 - Mon, Dec 21

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

2h 05mnonstop

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

1h 50mnonstop

$308Southwest

Tue, Oct 13 - Wed, Oct 14

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

1h 55mnonstop

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

2h 00mnonstop

$308Southwest

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

$308Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$89

Best time to beat the crowds with an average 19% drop in price.

Most popular time to fly and prices are also 4% lower on average.

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

Schererville

Chesterton

Munster

Porter

Monticello

Saint John

Griffith

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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