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.

$116 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

Sat, Nov 21 - Tue, Nov 24

10:47 pm - 8:14 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

10h 27m1 stop Atlanta Hartsfield-Jackson

9:09 am - 3:03 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

4h 54m1 stop Atlanta Hartsfield-Jackson

$220Frontier

Sat, Nov 21 - Tue, Nov 24

9:56 pm - 7:47 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

10h 51m1 stop Dallas/Fort Worth

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

6h 14m1 stop Atlanta Hartsfield-Jackson

$220Frontier

Wed, Dec 23 - Wed, Dec 30

7:50 am - 9:19 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 29mnonstop

9:57 am - 12:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$247American Airlines

Tue, Dec 22 - Tue, Dec 29

8:39 am - 10:08 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 29mnonstop

7:30 pm - 10:32 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$247American Airlines

Sat, Dec 5 - Sun, Dec 13

6:00 pm - 12:54 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

7h 54m1 stop Denver Intl

11:49 am - 4:55 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

28h 06m2 stops Minneapolis St Paul Denver Intl

$256Multiple Airlines

Thu, Dec 10 - Tue, Dec 15

6:00 pm - 10:46 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

17h 46m2 stops Denver Intl Minneapolis St Paul

7:25 am - 4:55 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

8h 30m1 stop Denver Intl

$259Multiple Airlines

Wed, Jan 27 - Mon, Feb 1

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

2h 10mnonstop

4:05 pm - 7:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 55mnonstop

$277Southwest

Tue, Dec 15 - Sat, Dec 19

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

2h 05mnonstop

5:30 am - 8:20 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$277Southwest

Thu, Jan 14 - Mon, Jan 18

1:01 pm - 2:23 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 22mnonstop

6:00 pm - 9:05 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$277United Airlines

Thu, Jan 21 - Thu, Jan 21

6:20 am - 7:42 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 22mnonstop

7:45 pm - 10:48 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 03mnonstop

$277United Airlines

Recent last minute flight deals from District of Columbia to Chicago

Tue, Nov 10 - Thu, Nov 12

11:16 am - 5:07 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

6h 51m1 stop Orlando

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

11h 16m1 stop Fort Lauderdale

$233Frontier

Tue, Nov 10 - Thu, Nov 12

11:16 am - 5:07 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

6h 51m1 stop Orlando

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

11h 16m1 stop Fort Lauderdale

$234Frontier

Mon, Nov 9 - Fri, Nov 13

6:36 pm - 5:07 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

23h 31m2 stops Blountville Tri Cities TN/VA Orlando

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

11h 16m1 stop Fort Lauderdale

$282Multiple Airlines

Mon, Nov 9 - Sat, Nov 14

6:36 pm - 5:07 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

23h 31m2 stops Blountville Tri Cities TN/VA Orlando

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

11h 16m1 stop Fort Lauderdale

$282Multiple Airlines

Tue, Nov 10 - Mon, Nov 30

2:54 pm - 4:18 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 24mnonstop

8:54 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$466American Airlines

Thu, Nov 5 - Mon, Nov 30

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

2h 31mnonstop

8:54 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$470American Airlines

Sat, Nov 7 - Sat, Nov 7

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

2h 19mnonstop

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

2h 02mnonstop

$476United Airlines

Thu, Nov 5 - Thu, Nov 5

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

2h 19mnonstop

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

2h 02mnonstop

$476United Airlines

Sat, Nov 7 - Sat, Nov 14

2:35 pm - 3:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

5:50 am - 8:45 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 55mnonstop

$481Southwest

Fri, Nov 6 - Sun, Nov 8

12:40 pm - 1:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

7:20 am - 10:10 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$481Southwest

Recent direct flight deals from District of Columbia to Chicago

Wed, Dec 23 - Wed, Dec 30

7:50 am - 9:19 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 29mnonstop

9:57 am - 12:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$247American Airlines

Tue, Dec 22 - Tue, Dec 29

8:39 am - 10:08 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 29mnonstop

7:30 pm - 10:32 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$247American Airlines

Wed, Dec 23 - Mon, Dec 28

8:59 pm - 10:33 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 34mnonstop

7:30 pm - 10:32 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$248American Airlines

Thu, Dec 24 - Thu, Dec 31

3:03 pm - 4:28 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 25mnonstop

7:30 pm - 10:32 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$249American Airlines

Fri, Nov 27 - Fri, Dec 4

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

2h 23mnonstop

10:35 am - 1:38 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 03mnonstop

$277United Airlines

Fri, Dec 11 - Mon, Dec 14

10:15 pm - 11:29 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 14mnonstop

6:15 pm - 9:18 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 03mnonstop

$277United Airlines

Wed, Jan 27 - Mon, Feb 1

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

2h 10mnonstop

4:05 pm - 7:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 55mnonstop

$277Southwest

Tue, Dec 15 - Sat, Dec 19

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

2h 05mnonstop

5:30 am - 8:20 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$277Southwest

Fri, Dec 18 - Tue, Dec 22

8:15 am - 9:40 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 25mnonstop

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

2h 03mnonstop

$277United Airlines

Tue, Dec 1 - Thu, Dec 31

6:50 pm - 8:00 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 10mnonstop

1:30 pm - 4:15 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$277Southwest

Useful Info

Low season	February
High season	July
Cheapest flight	$116

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

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

Flight from Reagan Washington National 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

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

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$116 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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More options for your flight to Chicago

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

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