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.

$117 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

Mon, Jan 11 - Sat, Jan 16

5:30 am - 4:46 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

12h 16m1 stop Atlanta Hartsfield-Jackson

10:46 am - 11:43 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

11h 57m2 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson

$222Frontier

Sat, Dec 5 - Mon, Dec 7

10:35 pm - 4:06 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

18h 31m1 stop Atlanta Hartsfield-Jackson

5:02 pm - 2:49 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

20h 47m1 stop Atlanta Hartsfield-Jackson

$223Frontier

Wed, Feb 24 - Wed, Mar 3

6:03 am - 4:41 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

11h 38m1 stop Minneapolis St Paul

12:42 pm - 10:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

8h 18m1 stop Minneapolis St Paul

$263Delta

Wed, Feb 24 - Sat, Feb 27

6:03 am - 4:41 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

11h 38m1 stop Minneapolis St Paul

9:46 am - 11:46 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

13h 00m1 stop Minneapolis St Paul

$263Delta

Wed, Dec 23 - Fri, Dec 25

5:06 pm - 6:30 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 24mnonstop

7:00 am - 10:01 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 01mnonstop

$273American Airlines

Thu, Dec 3 - Mon, Dec 7

7:58 pm - 9:24 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

7:33 pm - 10:35 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$277American Airlines

Thu, Feb 18 - Mon, Feb 22

9:35 am - 10:45 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 10mnonstop

4:55 pm - 7:45 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$277Southwest

Sat, Dec 5 - Sat, Dec 12

9:25 am - 10:30 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

3:30 pm - 6:15 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$277Southwest

Thu, Feb 11 - Mon, Feb 15

12:55 pm - 2:18 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 23mnonstop

9:25 pm - 12:19 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 54mnonstop

$277United Airlines

Thu, Dec 17 - Sat, Jan 9

1:05 pm - 2:29 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 24mnonstop

8:40 am - 11:42 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

$277United Airlines

Recent last minute flight deals from District of Columbia to Chicago

Wed, Nov 11 - Mon, Nov 16

7:48 am - 6:30 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

11h 42m1 stop Atlanta Hartsfield-Jackson

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

11h 16m1 stop Fort Lauderdale

$230Frontier

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

$241Frontier

Fri, Nov 13 - Tue, Nov 24

6:36 pm - 8:46 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

15h 10m2 stops Blountville Tri Cities TN/VA Orlando

6:20 am - 1:25 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

6h 05m1 stop Tampa

$332Multiple Airlines

Fri, Nov 13 - Sat, Nov 21

6:36 pm - 8:46 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

15h 10m2 stops Blountville Tri Cities TN/VA Orlando

7:49 am - 3:03 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

6h 14m1 stop Atlanta Hartsfield-Jackson

$349Multiple Airlines

Tue, Nov 10 - Fri, Dec 11

7:58 pm - 9:29 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 31mnonstop

7:49 am - 10:50 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 01mnonstop

$413American Airlines

Fri, Nov 13 - Fri, Dec 11

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

2h 26mnonstop

7:33 pm - 10:35 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$420American Airlines

Tue, Nov 10 - Fri, Dec 11

1:00 pm - 2:10 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 10mnonstop

5:10 pm - 7:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$420Southwest

Fri, Nov 13 - Fri, Dec 11

2:40 pm - 3:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

9:05 pm - 11:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$420Southwest

Fri, Nov 13 - Fri, Dec 11

6:11 am - 7:30 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 19mnonstop

2:30 pm - 5:32 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

$438United Airlines

Tue, Nov 10 - Fri, Dec 11

3:37 pm - 5:00 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 23mnonstop

2:30 pm - 5:32 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

$438United Airlines

Recent direct flight deals from District of Columbia to Chicago

Wed, Dec 23 - Fri, Dec 25

5:06 pm - 6:30 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 24mnonstop

7:00 am - 10:01 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 01mnonstop

$273American Airlines

Thu, Feb 11 - Mon, Feb 15

12:55 pm - 2:18 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 23mnonstop

9:25 pm - 12:19 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 54mnonstop

$277United Airlines

Thu, Feb 18 - Mon, Feb 22

9:35 am - 10:45 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 10mnonstop

4:55 pm - 7:45 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$277Southwest

Thu, Jan 7 - Mon, Jan 11

6:10 am - 7:20 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 10mnonstop

8:10 pm - 11:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$277Southwest

Thu, Dec 3 - Mon, Dec 7

7:58 pm - 9:24 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

7:33 pm - 10:35 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$277American Airlines

Fri, Jan 15 - Tue, Jan 19

9:10 am - 10:35 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 25mnonstop

4:47 pm - 7:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 12mnonstop

$277American Airlines

Thu, Dec 17 - Sat, Jan 9

1:05 pm - 2:29 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 24mnonstop

8:40 am - 11:42 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 02mnonstop

$277United Airlines

Tue, Dec 1 - Thu, Dec 3

1:00 pm - 2:15 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 15mnonstop

12:05 pm - 2:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$277Southwest

Fri, Dec 4 - Mon, Dec 7

1:00 pm - 2:23 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 23mnonstop

9:35 pm - 12:24 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 49mnonstop

$277United Airlines

Fri, Dec 4 - Fri, Dec 11

3:59 pm - 5:24 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 25mnonstop

5:00 pm - 7:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 59mnonstop

$277American Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$117

Best time to beat the crowds with an average 24% drop in price.

Most popular time to fly with an average 13% increase in price.

Flight from Washington Dulles Airport to Chicago O'Hare 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

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

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$117 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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High season

Cheapest flight

FAQs for booking flights from District of Columbia 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

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Flights from domestic origins to Chicago

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Find deals for your return flight