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.

$111 CHEAP FLIGHTS from Virginia to Chicago

Save 26% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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, Jan 6 - Sat, Jan 9

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, 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, Feb 4 - Sun, Feb 7

5:14 pm - 7:42 pmORF Norfolk-MDW Chicago Midway

27h 28m1 stop Orlando

8:47 pm - 4:19 pmMDW Chicago Midway-ORF Norfolk

18h 32m1 stop Orlando

$300Frontier

Tue, Dec 8 - Tue, Dec 15

6:30 am - 11:33 pmORF Norfolk-ORD Chicago O'Hare Intl

18h 03m1 stop Fort Lauderdale

7:00 am - 8:59 pmORD Chicago O'Hare Intl-ORF Norfolk

12h 59m1 stop Fort Lauderdale

$303JetBlue

Tue, Dec 8 - Tue, Dec 15

6:30 am - 11:33 pmORF Norfolk-ORD Chicago O'Hare Intl

18h 03m1 stop Fort Lauderdale

7:00 am - 8:59 pmORD Chicago O'Hare Intl-ORF Norfolk

12h 59m1 stop Fort Lauderdale

$303JetBlue

Wed, Dec 2 - Thu, Dec 10

7:24 pm - 7:17 amORF Norfolk-ORD Chicago O'Hare Intl

12h 53m1 stop Atlanta Hartsfield-Jackson

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

19h 02m1 stop Atlanta Hartsfield-Jackson

$306Frontier

Mon, Dec 7 - Wed, Dec 9

6:00 am - 9:29 pmORF Norfolk-ORD Chicago O'Hare Intl

16h 29m2 stops Orlando Atlanta Hartsfield-Jackson

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

9h 01m1 stop Atlanta Hartsfield-Jackson

$306Multiple Airlines

Tue, Jan 12 - Sat, Jan 16

8:30 pm - 10:15 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

14h 45m1 stop Tampa

4:47 pm - 2:18 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

20h 31m2 stops Fort Lauderdale Jacksonville

$313Multiple 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 - Wed, Dec 16

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

2h 05mnonstop

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

1h 45mnonstop

$319Southwest

Recent last minute flight deals from Virginia to Chicago

Tue, Nov 17 - Mon, Nov 23

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

5h 46m1 stop Atlanta Hartsfield-Jackson

7:49 am - 6:49 pmORD Chicago O'Hare Intl-ORF Norfolk

10h 00m1 stop Atlanta Hartsfield-Jackson

$310Frontier

Tue, Nov 17 - Mon, Nov 23

1:44 pm - 11:47 pmORF Norfolk-MDW Chicago Midway

11h 03m1 stop Atlanta Hartsfield-Jackson

9:09 am - 6:49 pmMDW Chicago Midway-ORF Norfolk

8h 40m1 stop Atlanta Hartsfield-Jackson

$320Frontier

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

Sat, Nov 14 - Wed, Nov 18

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

Wed, Nov 18 - Mon, Nov 30

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

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

5:55 pm - 9:01 pmORD Chicago O'Hare Intl-ROA Roanoke

2h 06mnonstop

$441United Airlines

Sat, Nov 14 - Sat, Nov 14

5:10 pm - 6:43 pmRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

2h 33mnonstop

9:20 pm - 12:34 amORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 14mnonstop

$446United Airlines

Sun, Nov 15 - Wed, Nov 18

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

17h 53m1 stop Orlando

12:15 pm - 9:32 amORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

20h 17m2 stops Quincy Regional Nashville Intl

$453Multiple Airlines

Sat, Nov 14 - Sun, Nov 15

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

4h 40m1 stop Baltimore/Washington

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

2h 00mnonstop

$461Southwest

Tue, Nov 17 - Thu, Nov 19

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

2h 05mnonstop

6:00 am - 11:40 amMDW Chicago Midway-RIC Richmond Byrd Intl

4h 40m1 stop Baltimore/Washington

$461Southwest

Sat, Nov 14 - Sun, Nov 15

8:30 am - 1:45 pmROA Roanoke-ORD Chicago O'Hare Intl

6h 15m1 stop New York LaGuardia

6:15 pm - 12:19 amORD Chicago O'Hare Intl-ROA Roanoke

5h 04m1 stop Atlanta Hartsfield-Jackson

$479Delta

Recent direct flight deals from Virginia to Chicago

Wed, Jan 6 - Sat, Jan 9

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, 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

Fri, Jan 1 - Sun, Jan 3

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

Tue, Mar 2 - Sun, Mar 7

1:38 pm - 3:00 pmSHD Staunton Shenandoah Valley-ORD Chicago O'Hare Intl

2h 22mnonstop

6:24 pm - 9:32 pmORD Chicago O'Hare Intl-SHD Staunton Shenandoah Valley

2h 08mnonstop

$254American Airlines

Tue, Dec 8 - Tue, Dec 15

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

2h 15mnonstop

6:25 pm - 9:30 pmMDW Chicago Midway-ORF Norfolk

2h 05mnonstop

$319Southwest

Wed, Dec 9 - Wed, Dec 16

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

2h 05mnonstop

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

1h 45mnonstop

$319Southwest

Wed, Dec 23 - Wed, Dec 23

8:00 am - 9:34 amRIC Richmond Byrd Intl-ORD Chicago O'Hare Intl

2h 34mnonstop

4:20 pm - 7:40 pmORD Chicago O'Hare Intl-RIC Richmond Byrd Intl

2h 20mnonstop

$319United Airlines

Tue, Dec 8 - Tue, Dec 15

12:15 pm - 1:59 pmORF Norfolk-ORD Chicago O'Hare Intl

2h 44mnonstop

5:59 pm - 9:21 pmORD Chicago O'Hare Intl-ORF Norfolk

2h 22mnonstop

$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, Jan 13 - Sat, Jan 16

4:50 pm - 6:36 pmORF Norfolk-ORD Chicago O'Hare Intl

2h 46mnonstop

5:59 pm - 9:27 pmORD Chicago O'Hare Intl-ORF Norfolk

2h 28mnonstop

$319United Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$111

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 Richmond 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

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

More options for your flight to Chicago

Add a hotel or car rental

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago

$111 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