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.

$95 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

Wed, Oct 28 - Thu, Oct 29

5:27 pm - 11:00 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 33m1 stop Charlotte Douglas

3:16 pm - 9:44 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

5h 28m1 stop Columbus

$180American Airlines

Tue, Sep 29 - Wed, Sep 30

7:50 am - 6:23 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

11h 33m1 stop Atlanta Hartsfield-Jackson

1:21 pm - 6:20 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

15h 59m1 stop Las Vegas Harry Reid Intl

$180Frontier

Tue, Sep 29 - Wed, Sep 30

7:50 am - 6:23 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

11h 33m1 stop Atlanta Hartsfield-Jackson

6:00 am - 3:34 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

8h 34m1 stop Dallas/Fort Worth

$180Frontier

Sun, Sep 27 - Wed, Sep 30

1:56 pm - 9:20 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

20h 24m1 stop Atlanta Hartsfield-Jackson

7:11 am - 10:02 amORD Chicago O'Hare Intl-RDU Raleigh-Durham

25h 51m2 stops Fort Lauderdale Tallahassee

$237Multiple Airlines

Mon, Oct 5 - Sat, Oct 10

7:43 pm - 3:20 pmRDU Raleigh-Durham-ORD Chicago O'Hare Intl

20h 37m2 stops Birmingham Fort Lauderdale

6:00 am - 12:28 amORD Chicago O'Hare Intl-RDU Raleigh-Durham

17h 28m1 stop Atlanta Hartsfield-Jackson

$237Multiple Airlines

Thu, Oct 1 - Sat, Oct 3

7:20 pm - 8:20 pmRDU Raleigh-Durham-MDW Chicago Midway

2h 00mnonstop

4:20 pm - 7:15 pmMDW Chicago Midway-RDU Raleigh-Durham

1h 55mnonstop

$257Southwest

Mon, Nov 9 - Wed, Nov 11

7:15 pm - 8:20 pmRDU Raleigh-Durham-MDW Chicago Midway

2h 05mnonstop

1:15 pm - 4:05 pmMDW Chicago Midway-RDU Raleigh-Durham

1h 50mnonstop

$257Southwest

Tue, Dec 22 - Tue, Dec 29

8:00 am - 9:34 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 34mnonstop

6:25 pm - 9:34 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 09mnonstop

$257United Airlines

Wed, Oct 7 - Wed, Oct 14

6:05 am - 7:27 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 22mnonstop

7:25 am - 10:48 amORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 23mnonstop

$257United Airlines

Sat, Nov 7 - Sat, Nov 7

6:02 am - 7:37 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 35mnonstop

4:30 pm - 7:45 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 15mnonstop

$257American Airlines

Recent last minute flight deals from Virginia to Chicago

Wed, Sep 9 - Tue, Oct 20

7:50 am - 6:23 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

11h 33m1 stop Atlanta Hartsfield-Jackson

8:04 am - 8:11 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

11h 07m1 stop Fort Lauderdale

$222Frontier

Wed, Sep 9 - Sat, Sep 12

7:50 am - 5:51 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

11h 01m1 stop Atlanta Hartsfield-Jackson

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

9h 53m1 stop Atlanta Hartsfield-Jackson

$237Frontier

Fri, Sep 11 - Fri, Sep 18

9:03 pm - 5:51 pmRDU Raleigh-Durham-MDW Chicago Midway

21h 48m2 stops Orlando Atlanta Hartsfield-Jackson

6:25 am - 12:38 pmMDW Chicago Midway-RDU Raleigh-Durham

5h 13m1 stop Atlanta Hartsfield-Jackson

$319Multiple Airlines

Wed, Sep 9 - Sat, Sep 12

9:47 pm - 10:59 pmRDU Raleigh-Durham-ORD Chicago O'Hare Intl

26h 12m1 stop Orlando

6:30 am - 5:22 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

9h 52m1 stop Denver Intl

$320Multiple Airlines

Thu, Sep 10 - Sun, Sep 13

5:51 pm - 7:05 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 14mnonstop

6:56 am - 10:01 amORD Chicago O'Hare Intl-GSO Greensboro/H. Point

2h 05mnonstop

$349United Airlines

Thu, Sep 10 - Sun, Sep 13

10:37 am - 11:49 amGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 12mnonstop

6:56 am - 10:01 amORD Chicago O'Hare Intl-GSO Greensboro/H. Point

2h 05mnonstop

$349United Airlines

Fri, Sep 11 - Mon, Sep 14

6:43 pm - 8:21 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 38mnonstop

7:39 pm - 10:49 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

2h 10mnonstop

$349American Airlines

Fri, Sep 11 - Mon, Sep 14

7:20 am - 8:45 amGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 25mnonstop

10:30 am - 1:37 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

2h 07mnonstop

$349American Airlines

Thu, Sep 10 - Thu, Sep 24

12:26 pm - 4:37 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

5h 11m1 stop Atlanta Hartsfield-Jackson

6:00 am - 11:45 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

4h 45m1 stop New York John F Kennedy Intl

$362Delta

Fri, Sep 11 - Mon, Sep 14

7:00 am - 12:41 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

6h 41m1 stop Atlanta Hartsfield-Jackson

9:46 am - 5:59 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

7h 13m1 stop Atlanta Hartsfield-Jackson

$369Delta

Recent direct flight deals from Virginia to Chicago

Thu, Oct 1 - Sat, Oct 3

7:20 pm - 8:20 pmRDU Raleigh-Durham-MDW Chicago Midway

2h 00mnonstop

4:20 pm - 7:15 pmMDW Chicago Midway-RDU Raleigh-Durham

1h 55mnonstop

$257Southwest

Mon, Nov 9 - Wed, Nov 11

7:15 pm - 8:20 pmRDU Raleigh-Durham-MDW Chicago Midway

2h 05mnonstop

1:15 pm - 4:05 pmMDW Chicago Midway-RDU Raleigh-Durham

1h 50mnonstop

$257Southwest

Sat, Nov 7 - Sat, Nov 7

6:02 am - 7:37 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 35mnonstop

4:30 pm - 7:45 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 15mnonstop

$257American Airlines

Sat, Oct 17 - Wed, Oct 21

1:52 pm - 3:29 pmRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 37mnonstop

9:59 am - 1:18 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 19mnonstop

$257American Airlines

Tue, Dec 22 - Tue, Dec 29

8:00 am - 9:34 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 34mnonstop

6:25 pm - 9:34 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 09mnonstop

$257United Airlines

Wed, Oct 7 - Wed, Oct 14

6:05 am - 7:27 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 22mnonstop

7:25 am - 10:48 amORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 23mnonstop

$257United Airlines

Wed, Oct 21 - Wed, Oct 21

7:00 am - 8:00 amRDU Raleigh-Durham-MDW Chicago Midway

2h 00mnonstop

6:10 pm - 9:10 pmMDW Chicago Midway-RDU Raleigh-Durham

2h 00mnonstop

$257Southwest

Tue, Sep 29 - Tue, Oct 6

6:25 pm - 7:20 pmRDU Raleigh-Durham-MDW Chicago Midway

1h 55mnonstop

6:10 pm - 9:10 pmMDW Chicago Midway-RDU Raleigh-Durham

2h 00mnonstop

$257Southwest

Thu, Oct 1 - Mon, Oct 5

6:00 am - 7:31 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 31mnonstop

9:00 pm - 12:05 amORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 05mnonstop

$257American Airlines

Sat, Oct 31 - Sat, Nov 7

5:40 pm - 7:00 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 20mnonstop

6:20 pm - 9:32 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

2h 12mnonstop

$289United Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$95

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

Most popular time to fly and prices are also 11% lower on average.

Flight from Washington Dulles Airport 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

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

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$95 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

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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

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Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight