How does KAYAK find such low prices on flights from District of Columbia 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 District of Columbia to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from District of Columbia to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from District of Columbia 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 District of Columbia 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 District of Columbia with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from District of Columbia 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 District of Columbia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$110 CHEAP FLIGHTS from District of Columbia to Chicago

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Flight Deals

Cheap Flights from District of Columbia 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 District of Columbia to Chicago

Thu, Nov 12 - Sat, Nov 14

6:07 pm - 3:37 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

22h 30m1 stop Fort Lauderdale

7:55 am - 8:11 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

11h 16m1 stop Fort Lauderdale

$210Frontier

Mon, Dec 7 - Sat, Dec 12

10:35 pm - 2:30 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

16h 55m1 stop Atlanta Hartsfield-Jackson

8:30 am - 2:49 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

5h 19m1 stop Atlanta Hartsfield-Jackson

$210Frontier

Fri, Dec 4 - Sun, Dec 6

8:15 am - 9:37 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

8:52 am - 11:53 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 01mnonstop

$218United Airlines

Thu, Dec 3 - Sun, Dec 6

10:10 am - 11:33 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 23mnonstop

8:52 am - 11:53 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 01mnonstop

$218United Airlines

Tue, Dec 1 - Thu, Dec 3

2:50 pm - 4:18 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 28mnonstop

5:53 pm - 8:58 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$227American Airlines

Wed, Nov 18 - Thu, Nov 19

3:55 pm - 5:27 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 32mnonstop

10:56 am - 1:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 03mnonstop

$227American Airlines

Tue, Nov 17 - Tue, Nov 24

6:10 am - 7:15 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

5:35 am - 8:25 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$228Southwest

Tue, Jan 12 - Wed, Jan 13

9:40 am - 10:50 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 10mnonstop

9:00 pm - 11:45 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$228Southwest

Sat, Nov 14 - Mon, Nov 16

6:00 pm - 12:21 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

7h 21m1 stop Denver Intl

7:00 am - 9:08 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

13h 08m1 stop Fort Lauderdale

$244Multiple Airlines

Wed, Dec 23 - Wed, Dec 23

6:00 am - 9:49 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 49m1 stop Detroit Metropolitan Wayne County

5:55 pm - 11:05 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

4h 10m1 stop Detroit Metropolitan Wayne County

$247Delta

Recent last minute flight deals from District of Columbia to Chicago

Sat, Oct 24 - Sat, Oct 31

11:12 am - 7:31 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

21h 19m1 stop Orlando

9:51 am - 11:21 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

24h 30m1 stop Orlando

$280Frontier

Sat, Oct 24 - Tue, Oct 27

7:00 am - 12:24 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

18h 24m1 stop Denver Intl

6:30 am - 12:09 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

28h 39m1 stop Denver Intl

$300Frontier

Sun, Oct 25 - Thu, Dec 24

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

2h 14mnonstop

2:22 pm - 5:22 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 00mnonstop

$405United Airlines

Tue, Oct 20 - Thu, Feb 25

10:22 am - 11:45 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 23mnonstop

9:05 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 54mnonstop

$415American Airlines

Sun, Oct 25 - Wed, Dec 23

10:15 am - 11:39 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 24mnonstop

9:35 pm - 12:38 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 03mnonstop

$418United Airlines

Thu, Oct 22 - Mon, Oct 26

12:30 pm - 6:56 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

7h 26m1 stop Dallas/Fort Worth

8:36 am - 5:56 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

8h 20m2 stops Orlando Blountville Tri Cities TN/VA

$421Multiple Airlines

Tue, Oct 20 - Thu, Feb 25

10:01 am - 1:05 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 04m1 stop Dayton

7:49 am - 10:55 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 06mnonstop

$425American Airlines

Tue, Oct 20 - Sat, Oct 31

6:20 am - 11:24 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 04m1 stop New York John F Kennedy Intl

1:00 pm - 8:09 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

6h 09m1 stop Boston Logan Intl

$447JetBlue

Wed, Oct 21 - Wed, Oct 21

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

2h 00mnonstop

4:50 pm - 7:40 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$501Southwest

Wed, Oct 21 - Wed, Oct 21

7:25 am - 12:25 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

6h 00m1 stop Atlanta Hartsfield-Jackson

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

1h 50mnonstop

$511Southwest

Recent direct flight deals from District of Columbia to Chicago

Fri, Dec 4 - Sun, Dec 6

8:15 am - 9:37 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

8:52 am - 11:53 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 01mnonstop

$218United Airlines

Thu, Dec 3 - Sun, Dec 6

10:10 am - 11:33 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 23mnonstop

8:52 am - 11:53 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 01mnonstop

$218United Airlines

Sat, Dec 5 - Sun, Dec 6

8:15 am - 9:37 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

8:52 am - 11:53 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 01mnonstop

$218United Airlines

Tue, Dec 1 - Thu, Dec 3

2:50 pm - 4:18 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 28mnonstop

5:53 pm - 8:58 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$227American Airlines

Wed, Nov 18 - Thu, Nov 19

3:55 pm - 5:27 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 32mnonstop

10:56 am - 1:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 03mnonstop

$227American Airlines

Wed, Nov 18 - Thu, Nov 19

1:15 pm - 2:38 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 23mnonstop

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

2h 02mnonstop

$227United Airlines

Tue, Nov 17 - Tue, Nov 24

6:10 am - 7:15 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

5:35 am - 8:25 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$228Southwest

Tue, Jan 12 - Wed, Jan 13

9:40 am - 10:50 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 10mnonstop

9:00 pm - 11:45 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$228Southwest

Sat, Dec 5 - Wed, Dec 9

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

2h 05mnonstop

7:25 am - 10:15 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$230Southwest

Thu, Nov 26 - Sat, Nov 28

8:43 am - 10:15 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 32mnonstop

6:56 am - 10:00 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$271American Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$110

Best time to beat the crowds with an average 23% drop in price.

Most popular time to fly with an average 15% increase in price.

Flight from Washington Dulles Airport to Chicago Midway Airport

How does KAYAK find such low prices on flights from District of Columbia 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 District of Columbia to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from District of Columbia to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from District of Columbia 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 District of Columbia 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 District of Columbia with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from District of Columbia 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 District of Columbia 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

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

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$110 Find Cheap Flights from District of Columbia to Chicago - Compare and Save

Cheap Flights from District of Columbia to Chicago

Recent round-trip flight deals from District of Columbia to Chicago

Recent one-way flight deals from District of Columbia to Chicago

Recent last minute flight deals from District of Columbia to Chicago

Recent direct flight deals from District of Columbia to Chicago

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Cheapest flight

FAQs for booking flights from District of Columbia to Chicago

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Complete your trip to Chicago with a hotel stay or car rental

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