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

Wed, Sep 30 - Tue, Oct 6

7:00 am - 12:23 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

18h 23m1 stop Denver Intl

6:30 am - 12:11 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

28h 41m1 stop Denver Intl

$177Frontier

Sat, Sep 26 - Sat, Oct 3

3:58 pm - 5:28 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

6:55 am - 9:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$177American Airlines

Thu, Oct 1 - Thu, Oct 1

8:30 am - 9:45 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 15mnonstop

4:00 pm - 7:09 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 09mnonstop

$177United Airlines

Wed, Sep 23 - Thu, Sep 24

11:57 am - 1:13 pmDCA 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

$177United Airlines

Sat, Sep 19 - Tue, Sep 22

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

2h 00mnonstop

11:10 am - 2:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Wed, Sep 23 - Wed, Oct 14

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

2h 10mnonstop

8:15 pm - 11:05 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Tue, Oct 13 - Tue, Oct 20

11:12 am - 7:51 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

21h 39m1 stop Orlando

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

11h 07m1 stop Fort Lauderdale

$177Frontier

Thu, Sep 17 - Sat, Sep 19

6:30 am - 7:58 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 28mnonstop

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

2h 04mnonstop

$177American Airlines

Tue, Sep 22 - Wed, Sep 23

11:10 am - 4:59 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 49m1 stop New York John F Kennedy Intl

5:10 pm - 11:02 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

4h 52m1 stop Detroit Metropolitan Wayne County

$194Delta

Tue, Sep 22 - Wed, Sep 23

9:40 am - 12:39 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

3h 59m1 stop Detroit Metropolitan Wayne County

1:00 pm - 8:37 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

6h 37m1 stop Atlanta Hartsfield-Jackson

$194Delta

Recent last minute flight deals from Virginia to Chicago

Wed, Sep 2 - Wed, Sep 30

8:39 pm - 7:53 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

12h 14m1 stop Atlanta Hartsfield-Jackson

7:11 am - 8:09 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

11h 58m1 stop Fort Lauderdale

$229Frontier

Fri, Sep 4 - Thu, Sep 17

9:54 pm - 11:08 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

26h 14m1 stop Orlando

11:15 am - 9:32 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

21h 17m1 stop Orlando

$229Frontier

Sat, Sep 5 - Wed, Sep 16

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

2h 00mnonstop

8:15 pm - 11:05 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$281Southwest

Sat, Sep 5 - Sat, Sep 26

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

2h 21mnonstop

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

2h 07mnonstop

$289American Airlines

Sat, Sep 5 - Wed, Sep 16

6:00 am - 11:00 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

6h 00m1 stop Orlando

11:10 am - 2:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$291Southwest

Sat, Sep 5 - Sat, Sep 26

6:49 pm - 8:24 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 35mnonstop

8:05 am - 2:56 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

5h 51m1 stop Charlotte Douglas

$299American Airlines

Sat, Sep 5 - Sun, Sep 6

12:34 pm - 4:17 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

4h 43m1 stop Detroit Metropolitan Wayne County

5:30 am - 10:25 amORD Chicago O'Hare Intl-GSO Greensboro/H. Point

3h 55m1 stop Atlanta Hartsfield-Jackson

$309Delta

Tue, Sep 1 - Wed, Sep 30

12:53 pm - 11:08 pmRDU Raleigh-Durham-ORD Chicago O'Hare Intl

11h 15m1 stop Orlando

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

25h 51m2 stops Fort Lauderdale Tallahassee

$322Multiple Airlines

Sat, Sep 5 - Mon, Sep 28

5:06 pm - 11:08 pmORF Norfolk-ORD Chicago O'Hare Intl

7h 02m1 stop Orlando

7:11 am - 10:43 pmORD Chicago O'Hare Intl-ORF Norfolk

14h 32m2 stops Fort Lauderdale Tampa

$326Multiple Airlines

Sat, Sep 5 - Sun, Sep 6

5:03 pm - 8:55 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

4h 52m1 stop Atlanta Hartsfield-Jackson

5:30 am - 1:29 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

6h 59m1 stop Atlanta Hartsfield-Jackson

$348Delta

Recent direct flight deals from Virginia to Chicago

Sat, Sep 19 - Tue, Sep 22

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

2h 00mnonstop

11:10 am - 2:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Wed, Sep 23 - Wed, Oct 14

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

2h 10mnonstop

8:15 pm - 11:05 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Thu, Nov 5 - Mon, Nov 9

8:23 am - 9:45 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

8:50 am - 11:52 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

$177United Airlines

Thu, Oct 22 - Sat, Oct 24

10:30 am - 11:48 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

12:55 pm - 4:01 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$177United Airlines

Sat, Sep 26 - Sat, Oct 3

3:58 pm - 5:28 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

6:55 am - 9:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$177American Airlines

Thu, Oct 15 - Mon, Oct 19

6:00 am - 7:27 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 27mnonstop

6:59 am - 10:06 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 07mnonstop

$177American Airlines

Wed, Oct 28 - Thu, Oct 29

3:10 pm - 4:10 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

11:10 am - 2:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Tue, Oct 13 - Thu, Oct 15

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

2h 00mnonstop

11:10 am - 2:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Thu, Sep 24 - Mon, Sep 28

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

2h 15mnonstop

8:50 am - 11:55 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

$177United Airlines

Thu, Sep 17 - Sat, Sep 19

6:30 am - 7:58 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 28mnonstop

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

2h 04mnonstop

$177American Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$89

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

Most popular time to fly and prices are also 8% 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

Munster

Schererville

Chesterton

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 $529

Premium Economy Class flights to Chicagofrom $537

Economy Class flights to Chicagofrom $233

$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

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Low season

High season

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