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

Thu, Oct 29 - Sat, Oct 31

7:40 am - 11:47 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

17h 07m1 stop Atlanta Hartsfield-Jackson

7:25 am - 5:12 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

8h 47m1 stop Atlanta Hartsfield-Jackson

$178Frontier

Tue, Oct 27 - Sat, Oct 31

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

5h 46m1 stop Atlanta Hartsfield-Jackson

7:15 am - 5:12 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

8h 57m1 stop Atlanta Hartsfield-Jackson

$180Frontier

Thu, Nov 12 - Sat, Nov 14

9:30 am - 10:50 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 20mnonstop

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

6h 27m1 stop Newark

$203United 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

$216Southwest

Sat, Oct 24 - Tue, Oct 27

3:40 pm - 4:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

9:10 am - 11:55 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$218Southwest

Fri, Dec 25 - Fri, Dec 25

3:10 pm - 6:36 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 26m1 stop Cleveland Hopkins Intl

8:52 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 07mnonstop

$221American Airlines

Thu, Nov 12 - Sat, Nov 14

1:15 pm - 6:31 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 16m1 stop Newark

6:00 pm - 9:11 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 11mnonstop

$225United Airlines

Thu, Oct 15 - Wed, Oct 21

1:16 pm - 6:31 pmRDU Raleigh-Durham-ORD Chicago O'Hare Intl

6h 15m1 stop Atlanta Hartsfield-Jackson

6:00 am - 6:10 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

11h 10m2 stops Atlanta Hartsfield-Jackson Orlando

$239Multiple Airlines

Mon, Oct 5 - Thu, Oct 8

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

20h 37m2 stops Birmingham Fort Lauderdale

7:44 pm - 12:21 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

15h 37m1 stop Atlanta Hartsfield-Jackson

$242Multiple Airlines

Thu, Oct 22 - Mon, Oct 26

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

2h 32mnonstop

6:40 pm - 9:48 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 08mnonstop

$257American Airlines

Recent last minute flight deals from Virginia to Chicago

Thu, Sep 17 - Sun, Sep 20

1:56 pm - 5:46 pmRDU Raleigh-Durham-MDW Chicago Midway

4h 50m1 stop Atlanta Hartsfield-Jackson

6:46 pm - 12:29 amMDW Chicago Midway-RDU Raleigh-Durham

4h 43m1 stop Atlanta Hartsfield-Jackson

$241Frontier

Sat, Sep 19 - Sat, Sep 26

6:00 am - 5:38 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

24h 38m1 stop Las Vegas Harry Reid Intl

7:32 pm - 6:20 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

9h 48m1 stop Las Vegas Harry Reid Intl

$270Frontier

Thu, Sep 17 - Sun, Sep 20

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

2h 31mnonstop

6:55 am - 1:28 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

5h 33m1 stop Washington, D.C. Reagan-National

$316American Airlines

Tue, Sep 15 - Fri, Sep 18

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

$346Multiple 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

$347Multiple Airlines

Sat, Sep 19 - Sun, Sep 27

2:08 pm - 3:30 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 22mnonstop

8:05 am - 3:45 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

6h 40m1 stop Charlotte Douglas

$363American Airlines

Tue, Sep 15 - Sat, Sep 19

10:16 am - 4:37 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

7h 21m1 stop Atlanta Hartsfield-Jackson

10:44 am - 4:05 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

4h 21m1 stop Atlanta Hartsfield-Jackson

$387Delta

Sat, Sep 19 - Sat, Sep 26

5:51 pm - 7:00 pmROA Roanoke-ORD Chicago O'Hare Intl

2h 09mnonstop

7:45 pm - 10:59 pmORD Chicago O'Hare Intl-ROA Roanoke

2h 14mnonstop

$394United Airlines

Sat, Sep 19 - Mon, Sep 21

6:35 am - 7:52 amGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 17mnonstop

6:25 am - 2:12 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

6h 47m1 stop Washington, D.C. Dulles Intl

$398United Airlines

Sat, Sep 19 - Mon, Sep 21

5:10 pm - 8:56 pmGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

4h 46m1 stop Atlanta Hartsfield-Jackson

8:05 am - 2:04 pmORD Chicago O'Hare Intl-GSO Greensboro/H. Point

4h 59m1 stop Atlanta Hartsfield-Jackson

$408Delta

Recent direct flight deals from Virginia to Chicago

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

$216Southwest

Wed, Feb 24 - Sat, Feb 27

7:00 pm - 8:20 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 20mnonstop

11:10 am - 1:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$218Southwest

Sat, Oct 24 - Tue, Oct 27

3:40 pm - 4:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

9:10 am - 11:55 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$218Southwest

Wed, Oct 14 - Thu, Oct 15

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

2h 00mnonstop

8:45 pm - 11:35 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$234Southwest

Wed, Oct 7 - Thu, Oct 8

4:29 pm - 6:08 pmRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 39mnonstop

6:40 pm - 9:48 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 08mnonstop

$257American Airlines

Tue, Dec 22 - Tue, Dec 29

3:48 pm - 5:29 pmRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 41mnonstop

10:00 am - 1:21 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 21mnonstop

$257American 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

Tue, Oct 20 - Sat, Oct 24

10:13 am - 11:37 amRDU Raleigh-Durham-ORD Chicago O'Hare Intl

2h 24mnonstop

10:33 am - 1:49 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 16mnonstop

$257United Airlines

Sat, Oct 10 - Wed, Oct 14

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

2h 29mnonstop

11:50 am - 2:57 pmORD Chicago O'Hare Intl-RDU Raleigh-Durham

2h 07mnonstop

$257American Airlines

Sat, Oct 10 - Tue, Oct 13

6:30 am - 7:47 amGSO Greensboro/H. Point-ORD Chicago O'Hare Intl

2h 17mnonstop

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

2h 06mnonstop

$289United Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$95

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 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

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

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Flights to other popular destinations

Find deals for your return flight