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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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 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

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, Jan 15 - Wed, Jan 20

12:57 pm - 3:56 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

27h 59m1 stop Orlando

10:18 am - 8:13 amORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

20h 55m1 stop Tampa

$311Multiple Airlines

Mon, Oct 26 - Thu, Oct 29

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

4h 45m1 stop Baltimore/Washington

2:30 pm - 11:55 pmMDW Chicago Midway-RIC Richmond Byrd Intl

8h 25m2 stops Nashville Intl Baltimore/Washington

$313Southwest

Wed, Dec 23 - Tue, Dec 29

7:19 pm - 1:09 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

6h 50m1 stop Orlando

2:31 pm - 6:24 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

26h 53m1 stop Orlando

$313Frontier

Wed, Oct 28 - Sat, Oct 31

7:41 pm - 6:45 pmORF Norfolk-ORD Chicago O'Hare Intl

24h 04m2 stops Orlando Atlanta Hartsfield-Jackson

7:15 am - 7:44 pmORD Chicago O'Hare Intl-ORF Norfolk

35h 29m2 stops Atlanta Hartsfield-Jackson Orlando

$316Frontier

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

Fri, Dec 4 - Sat, Dec 5

7:22 pm - 11:56 pmORF Norfolk-ORD Chicago O'Hare Intl

5h 34m1 stop Atlanta Hartsfield-Jackson

6:16 pm - 12:06 amORD Chicago O'Hare Intl-ORF Norfolk

4h 50m1 stop Atlanta Hartsfield-Jackson

$317Delta

Mon, Jan 11 - Sun, Jan 24

7:00 am - 9:13 amORF Norfolk-ORD Chicago O'Hare Intl

27h 13m1 stop Tampa

5:34 pm - 7:02 pmORD Chicago O'Hare Intl-ORF Norfolk

24h 28m2 stops Fort Myers SW Florida Intl Tweed-New Haven

$317Multiple Airlines

Recent last minute flight deals from Virginia to Chicago

Wed, Oct 14 - Wed, Oct 21

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

12h 50m1 stop Orlando

8:46 am - 6:46 pmORD Chicago O'Hare Intl-ORF Norfolk

9h 00m1 stop Orlando

$330Frontier

Wed, Oct 14 - Tue, Oct 20

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

2h 14mnonstop

6:50 pm - 9:56 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 15 - Wed, Oct 21

7:41 pm - 7:02 pmORF Norfolk-ORD Chicago O'Hare Intl

24h 21m1 stop Orlando

8:46 am - 6:46 pmORD Chicago O'Hare Intl-ORF Norfolk

9h 00m1 stop Orlando

$338Frontier

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

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

$420Multiple Airlines

Wed, Oct 14 - Wed, Oct 21

8:00 am - 6:31 pmORF Norfolk-ORD Chicago O'Hare Intl

11h 31m2 stops Orlando Atlanta Hartsfield-Jackson

7:44 pm - 12:38 pmORD Chicago O'Hare Intl-ORF Norfolk

15h 54m1 stop Atlanta Hartsfield-Jackson

$428Multiple Airlines

Thu, Oct 15 - Mon, Oct 19

7:10 am - 1:08 pmROA Roanoke-ORD Chicago O'Hare Intl

6h 58m1 stop New York LaGuardia

9:59 am - 10:49 pmORD Chicago O'Hare Intl-ROA Roanoke

11h 50m2 stops Minneapolis St Paul New York LaGuardia

$437Delta

Thu, Oct 15 - Mon, Oct 19

7:10 am - 1:08 pmROA Roanoke-ORD Chicago O'Hare Intl

6h 58m1 stop New York LaGuardia

1:25 pm - 12:27 amORD Chicago O'Hare Intl-ROA Roanoke

10h 02m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

$437Delta

Tue, Oct 13 - Sat, Oct 17

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

2h 07mnonstop

5:50 pm - 8:59 pmORD Chicago O'Hare Intl-CHO Charlottesville Albemarle

2h 09mnonstop

$475United Airlines

Recent direct 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, 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, Feb 24 - Sat, Feb 27

1:39 pm - 3:00 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 21mnonstop

6:24 pm - 9:26 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 02mnonstop

$234American Airlines

Fri, Oct 30 - Mon, Nov 2

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

2h 00mnonstop

7:00 pm - 9:55 pmMDW Chicago Midway-RIC Richmond Byrd Intl

1h 55mnonstop

$316Southwest

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, Feb 5 - Sun, Feb 7

9:04 am - 10:15 amROA Roanoke-ORD Chicago O'Hare Intl

2h 11mnonstop

10:25 am - 1:30 pmORD Chicago O'Hare Intl-ROA Roanoke

2h 05mnonstop

$319United Airlines

Thu, Oct 29 - Sun, Nov 1

5:51 pm - 6:59 pmROA Roanoke-ORD Chicago O'Hare Intl

2h 08mnonstop

6:29 am - 9:26 amORD Chicago O'Hare Intl-ROA Roanoke

1h 57mnonstop

$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

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 Richmond 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

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

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$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

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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

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Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight