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.

$94 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

Tue, Sep 29 - Wed, Sep 30

7:50 am - 5:46 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

10h 56m1 stop Atlanta Hartsfield-Jackson

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

9h 53m1 stop Atlanta Hartsfield-Jackson

$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

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

Fri, Sep 25 - Fri, Oct 2

6:00 am - 10:53 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

5h 53m1 stop Newark

9:00 am - 12:08 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 08mnonstop

$208United Airlines

Sun, Nov 1 - Tue, Nov 3

10:47 pm - 12:01 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 14mnonstop

5:00 am - 11:44 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

5h 44m1 stop Newark

$231United 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

Sun, Oct 4 - Wed, Oct 7

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

20h 24m1 stop Atlanta Hartsfield-Jackson

7:11 am - 10:07 amORD Chicago O'Hare Intl-RDU Raleigh-Durham

25h 56m2 stops Fort Lauderdale Tallahassee

$238Multiple Airlines

Wed, Oct 7 - Thu, Oct 15

9:30 am - 10:59 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 29mnonstop

8:55 pm - 11:59 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 04mnonstop

$257American Airlines

Thu, Oct 29 - Mon, Nov 2

6:00 am - 7:32 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 32mnonstop

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

2h 15mnonstop

$257American Airlines

Thu, Oct 1 - Mon, Oct 5

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

2h 00mnonstop

6:50 pm - 9:45 pmMDW Chicago Midway-RDU Raleigh-Durham

1h 55mnonstop

$257Southwest

Wed, Nov 4 - Thu, Nov 5

8:05 am - 9:10 amRDU Raleigh-Durham-MDW Chicago Midway

2h 05mnonstop

12:45 pm - 3:35 pmMDW Chicago Midway-RDU Raleigh-Durham

1h 50mnonstop

$257Southwest

Recent last minute flight deals from Virginia to Chicago

Tue, Sep 15 - Tue, Oct 13

11:12 am - 10:59 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

12h 47m1 stop Orlando

6:00 am - 5:13 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

10h 13m1 stop Atlanta Hartsfield-Jackson

$255Frontier

Sun, Sep 13 - Sat, Oct 10

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 - 5:13 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

10h 13m1 stop Atlanta Hartsfield-Jackson

$255Frontier

Fri, Sep 11 - Fri, Sep 18

6:46 pm - 10:59 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

29h 13m2 stops Blountville Tri Cities TN/VA Orlando

8:55 pm - 6:20 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

32h 25m1 stop Las Vegas Harry Reid Intl

$342Multiple Airlines

Tue, Sep 15 - Sat, Sep 19

4:42 pm - 10:59 pmRDU Raleigh-Durham-ORD Chicago O'Hare Intl

7h 17m1 stop Orlando

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

9h 52m1 stop Denver Intl

$351Multiple Airlines

Tue, Sep 15 - Wed, Sep 23

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

2h 25mnonstop

3:05 pm - 6:13 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

2h 08mnonstop

$353American Airlines

Tue, Sep 15 - Sat, Sep 19

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

2h 38mnonstop

3:26 pm - 6:34 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

2h 08mnonstop

$353American Airlines

Sun, Sep 13 - Sat, Oct 10

7:55 am - 8:50 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

1h 55mnonstop

6:15 pm - 9:10 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 55mnonstop

$400Southwest

Sun, Sep 13 - Thu, Oct 15

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

2h 05mnonstop

6:00 am - 8:50 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$400Southwest

Mon, Sep 14 - Mon, Sep 21

7:04 pm - 11:59 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

5h 55m1 stop Atlanta Hartsfield-Jackson

8:05 am - 3:12 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

6h 07m1 stop Atlanta Hartsfield-Jackson

$414Delta

Fri, Sep 11 - Mon, Sep 14

6:10 am - 9:07 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

3h 57m1 stop Detroit Metropolitan Wayne County

1:00 pm - 7:32 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

5h 32m1 stop Atlanta Hartsfield-Jackson

$493Delta

Recent direct flight deals from Virginia to Chicago

Wed, Oct 7 - Thu, Oct 15

9:30 am - 10:59 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 29mnonstop

8:55 pm - 11:59 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 04mnonstop

$257American Airlines

Thu, Oct 29 - Mon, Nov 2

6:00 am - 7:32 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 32mnonstop

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

2h 15mnonstop

$257American Airlines

Wed, Sep 30 - Mon, Oct 5

6:05 am - 7:28 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 23mnonstop

12:55 pm - 4:03 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 08mnonstop

$257United Airlines

Thu, Oct 15 - Sat, Oct 17

8:06 am - 9:30 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 24mnonstop

3:35 pm - 6:48 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 13mnonstop

$257United Airlines

Thu, Oct 1 - Mon, Oct 5

6:55 am - 7:55 amRDU Raleigh-Durham-MDW Chicago Midway

2h 00mnonstop

6:50 pm - 9:45 pmMDW Chicago Midway-RDU Raleigh-Durham

1h 55mnonstop

$257Southwest

Sat, Oct 3 - Mon, Oct 5

5:05 pm - 6:00 pmRDU Raleigh-Durham-MDW Chicago Midway

1h 55mnonstop

6:50 pm - 9:45 pmMDW Chicago Midway-RDU Raleigh-Durham

1h 55mnonstop

$257Southwest

Wed, Oct 7 - Tue, Oct 13

8:25 pm - 9:54 pmRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 29mnonstop

8:55 pm - 11:59 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 04mnonstop

$257American Airlines

Sat, Oct 24 - Wed, Oct 28

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

2h 37mnonstop

10:00 am - 1:19 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 19mnonstop

$257American Airlines

Thu, Oct 1 - Mon, Oct 5

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

2h 00mnonstop

6:50 pm - 9:45 pmMDW Chicago Midway-RDU Raleigh-Durham

1h 55mnonstop

$257Southwest

Sat, Oct 10 - Sun, Oct 11

10:45 am - 11:54 amGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 09mnonstop

6:55 am - 10:01 amORD Chicago O'Hare Intl-GSO Greensboro/H. Point

2h 06mnonstop

$294United Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$94

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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$94 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