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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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, Oct 27 - Thu, Oct 29

8:05 am - 12:51 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

5h 46m1 stop Atlanta Hartsfield-Jackson

10:26 am - 5:12 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

5h 46m1 stop Atlanta Hartsfield-Jackson

$179Frontier

Sat, Oct 24 - Sat, Oct 31

12:30 pm - 5:20 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

5h 50m1 stop New York John F Kennedy Intl

6:10 am - 11:50 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

4h 40m1 stop New York John F Kennedy Intl

$179Delta

Wed, Oct 28 - Wed, Oct 28

6:05 am - 10:29 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

5h 24m1 stop Detroit Metropolitan Wayne County

5:29 pm - 11:16 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

4h 47m1 stop Detroit Metropolitan Wayne County

$179Delta

Sat, Oct 17 - Sat, Oct 24

7:50 am - 6:31 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

11h 41m1 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

$180Frontier

Tue, Nov 3 - Sat, Nov 7

4:05 pm - 9:30 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 25m1 stop Newark

7:45 am - 10:53 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 08mnonstop

$181United Airlines

Wed, Nov 4 - Sat, Nov 7

8:10 pm - 9:44 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 34mnonstop

7:00 am - 2:27 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

6h 27m1 stop Newark

$196United Airlines

Tue, Nov 3 - Sat, Nov 7

7:50 am - 9:16 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

7:13 am - 10:14 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 01mnonstop

$209American Airlines

Sat, Oct 10 - Tue, Oct 13

6:33 pm - 8:06 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 33mnonstop

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

2h 05mnonstop

$209American Airlines

Wed, Oct 7 - Tue, Oct 13

9:00 pm - 10:00 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

5:40 am - 8:30 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$209Southwest

Tue, Oct 13 - Sat, Oct 17

7:30 am - 8:30 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

3:45 pm - 6:35 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$209Southwest

Recent last minute flight deals from Virginia to Chicago

Wed, Sep 23 - Wed, Sep 30

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

$290Frontier

Wed, Sep 23 - Tue, Sep 29

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

$290Frontier

Mon, Sep 21 - Mon, Oct 19

7:43 pm - 10:59 pmORF Norfolk-ORD Chicago O'Hare Intl

28h 16m1 stop Orlando

8:04 am - 12:04 pmORD Chicago O'Hare Intl-ORF Norfolk

27h 00m2 stops Fort Lauderdale Jacksonville

$361Multiple Airlines

Wed, Sep 23 - Wed, Sep 30

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

$367American Airlines

Wed, Sep 23 - Wed, Sep 30

2:12 pm - 3:30 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 18mnonstop

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

2h 07mnonstop

$367American Airlines

Thu, Sep 24 - Thu, Oct 1

6:48 am - 7:58 amROA Roanoke-ORD Chicago O'Hare Intl

2h 10mnonstop

6:55 am - 9:57 amORD Chicago O'Hare Intl-ROA Roanoke

2h 02mnonstop

$394United Airlines

Thu, Sep 24 - Thu, Oct 1

6:15 am - 11:48 amROA Roanoke-ORD Chicago O'Hare Intl

6h 33m1 stop Washington, D.C. Dulles Intl

6:55 am - 9:57 amORD Chicago O'Hare Intl-ROA Roanoke

2h 02mnonstop

$404United Airlines

Sat, Sep 19 - Fri, Sep 25

6:17 pm - 12:23 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

7h 06m1 stop Denver Intl

3:50 pm - 9:05 amORD Chicago O'Hare Intl-RDU Raleigh-Durham

16h 15m1 stop Orlando

$431Multiple Airlines

Sat, Sep 19 - Fri, Jun 18

1:15 pm - 7:15 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

7h 00m1 stop New York LaGuardia

1:15 pm - 9:15 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

7h 00m1 stop Atlanta Hartsfield-Jackson

$458Delta

Thu, Sep 24 - Wed, Sep 30

7:20 am - 12:59 pmROA Roanoke-ORD Chicago O'Hare Intl

6h 39m1 stop New York LaGuardia

2:29 pm - 10:48 pmORD Chicago O'Hare Intl-ROA Roanoke

7h 19m1 stop New York LaGuardia

$489Delta

Recent direct flight deals from Virginia to Chicago

Wed, Oct 7 - Tue, Oct 13

9:00 pm - 10:00 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

5:40 am - 8:30 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$209Southwest

Tue, Oct 13 - Sat, Oct 17

7:30 am - 8:30 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

3:45 pm - 6:35 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$209Southwest

Sat, Oct 10 - Tue, Oct 13

6:33 pm - 8:06 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 33mnonstop

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

2h 05mnonstop

$209American Airlines

Wed, Oct 14 - Wed, Oct 21

2:52 pm - 4:15 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 23mnonstop

1:18 pm - 4:27 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 09mnonstop

$209American Airlines

Wed, Oct 14 - Sat, Oct 17

7:29 pm - 8:49 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 20mnonstop

1:55 pm - 5:03 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 08mnonstop

$209United Airlines

Wed, Oct 7 - Wed, Oct 14

9:30 am - 10:47 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 17mnonstop

12:40 pm - 3:42 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$209United Airlines

Tue, Oct 13 - Tue, Oct 20

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

2h 00mnonstop

5:40 am - 8:30 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$209Southwest

Sat, Oct 10 - Tue, Oct 13

6:40 pm - 7:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

5:40 am - 8:30 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$209Southwest

Tue, Nov 3 - Sat, Nov 7

7:50 am - 9:16 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

7:13 am - 10:14 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 01mnonstop

$209American Airlines

Wed, Oct 7 - Tue, Oct 13

10:30 am - 11:46 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 16mnonstop

5:59 am - 8:54 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 55mnonstop

$209United Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$89

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

Most popular time to fly and prices are also 7% lower on average.

Flight from Reagan Washington National 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

Schererville

Chesterton

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

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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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