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.

$79 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, Sep 9 - Fri, Sep 11

6:35 am - 5:38 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

24h 03m1 stop Las Vegas Harry Reid Intl

10:26 am - 5:18 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

5h 52m1 stop Atlanta Hartsfield-Jackson

$181Frontier

Tue, Sep 8 - Fri, Sep 11

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$181Frontier

Wed, Nov 18 - Wed, Nov 18

2:40 pm - 5:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 05m1 stop Lambert-St Louis

8:35 pm - 11:20 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$183Southwest

Mon, Nov 16 - Wed, Nov 18

2:40 pm - 5:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 05m1 stop Lambert-St Louis

12:05 pm - 2:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$183Southwest

Wed, Oct 21 - Thu, Oct 22

5:30 pm - 10:17 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

5h 47m1 stop New York LaGuardia

5:29 pm - 11:07 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

4h 38m1 stop Detroit Metropolitan Wayne County

$197Delta

Wed, Oct 28 - Mon, Nov 2

9:32 am - 12:59 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 27m1 stop Detroit Metropolitan Wayne County

11:19 am - 4:39 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

4h 20m1 stop Detroit Metropolitan Wayne County

$197Delta

Sat, Oct 31 - Tue, Nov 3

7:45 am - 9:11 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

8:57 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$197American Airlines

Thu, Oct 15 - Mon, Oct 19

7:45 am - 9:11 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

5:59 am - 9:14 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 15mnonstop

$197American Airlines

Thu, Oct 8 - Mon, Oct 12

1:10 pm - 2:26 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 16mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$200United Airlines

Thu, Oct 8 - Mon, Oct 12

6:10 am - 7:25 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$200United Airlines

Recent last minute flight deals from Virginia to Chicago

Wed, Aug 26 - Mon, Sep 21

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$229Frontier

Wed, Aug 26 - Wed, Sep 9

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$229Frontier

Wed, Aug 26 - Wed, Sep 9

8:20 am - 9:38 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

6:30 am - 9:28 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 58mnonstop

$315United Airlines

Wed, Aug 26 - Mon, Sep 21

8:20 am - 9:38 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

8:42 am - 11:49 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 07mnonstop

$315United Airlines

Wed, Aug 26 - Mon, Sep 21

6:05 am - 7:00 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

1h 55mnonstop

9:00 pm - 11:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 55mnonstop

$315Southwest

Wed, Aug 26 - Wed, Sep 9

1:00 pm - 1:55 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

1h 55mnonstop

6:10 am - 8:55 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$315Southwest

Wed, Aug 26 - Wed, Sep 9

6:10 am - 9:17 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 07m1 stop Detroit Metropolitan Wayne County

5:37 pm - 11:02 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

4h 25m1 stop Detroit Metropolitan Wayne County

$335Delta

Sat, Aug 22 - Tue, Aug 25

1:40 pm - 3:00 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 20mnonstop

8:04 pm - 11:09 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

2h 05mnonstop

$347American Airlines

Tue, Aug 25 - Mon, Aug 31

2:50 pm - 8:55 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

7h 05m1 stop Atlanta Hartsfield-Jackson

5:30 am - 11:34 amORD Chicago O'Hare Intl-GSO Greensboro/H. Point

5h 04m1 stop Atlanta Hartsfield-Jackson

$353Delta

Sat, Aug 22 - Tue, Aug 25

7:49 am - 9:10 amGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 21mnonstop

5:05 am - 9:51 amORD Chicago O'Hare Intl-GSO Greensboro/H. Point

3h 46m1 stop Charlotte Douglas

$357American Airlines

Recent direct flight deals from Virginia to Chicago

Sat, Oct 31 - Tue, Nov 3

7:45 am - 9:11 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

8:57 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$197American Airlines

Thu, Oct 15 - Mon, Oct 19

7:45 am - 9:11 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

5:59 am - 9:14 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 15mnonstop

$197American Airlines

Sat, Sep 12 - Sat, Sep 19

8:40 am - 10:10 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

6:55 pm - 10:00 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$197American Airlines

Wed, Sep 9 - Sat, Sep 12

5:00 pm - 6:29 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 29mnonstop

8:55 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$197American Airlines

Thu, Oct 8 - Mon, Oct 12

1:10 pm - 2:26 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 16mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$200United Airlines

Thu, Oct 8 - Mon, Oct 12

6:10 am - 7:25 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$200United Airlines

Thu, Oct 8 - Mon, Oct 12

1:10 pm - 2:26 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 16mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$200United Airlines

Fri, Dec 4 - Mon, Dec 7

3:35 pm - 4:50 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 15mnonstop

7:25 am - 10:15 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$216Southwest

Fri, Oct 30 - Thu, Nov 5

8:40 pm - 9:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

7:20 am - 10:10 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$216Southwest

Fri, Sep 18 - Mon, Sep 21

9:15 pm - 10:15 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

9:00 pm - 11:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 55mnonstop

$216Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$79

Best time to beat the crowds with an average 18% drop in price.

Most popular time to fly and prices are also 10% lower on average.

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

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Virginia

First Class flights to Chicagofrom $430

Business Class flights to Chicagofrom $534

Premium Economy Class flights to Chicagofrom $499

Economy Class flights to Chicagofrom $233

$79 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

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Cheapest flight

FAQs for booking flights from Virginia to Chicago

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Virginia

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

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight