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.

$96 CHEAP FLIGHTS from District of Columbia to Chicago

Save 19% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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

Fri, Nov 20 - Thu, Nov 26

10:47 pm - 11:18 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

25h 31m1 stop Atlanta Hartsfield-Jackson

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

6h 14m1 stop Atlanta Hartsfield-Jackson

$206Frontier

Wed, Nov 18 - Wed, Nov 25

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

11h 42m1 stop Atlanta Hartsfield-Jackson

4:00 pm - 10:02 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

29h 02m1 stop Fort Lauderdale

$206Frontier

Sat, Nov 7 - Mon, Nov 9

8:39 am - 10:05 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

8:57 pm - 11:55 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 58mnonstop

$211American Airlines

Wed, Nov 4 - Mon, Nov 9

10:11 am - 11:34 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 23mnonstop

4:51 pm - 7:56 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$211American Airlines

Thu, Nov 5 - Tue, Nov 10

6:25 am - 7:43 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 18mnonstop

9:00 am - 12:03 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 03mnonstop

$211United Airlines

Thu, Dec 3 - Mon, Dec 7

7:41 am - 8:59 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 18mnonstop

5:00 pm - 8:11 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 11mnonstop

$211United Airlines

Tue, Nov 3 - Tue, Nov 10

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

2h 10mnonstop

8:35 pm - 11:20 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$211Southwest

Mon, Nov 2 - Wed, Nov 4

10:45 am - 11:50 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

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

1h 45mnonstop

$211Southwest

Sat, Oct 31 - Mon, Nov 2

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

7h 21m1 stop Denver Intl

2:50 pm - 9:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

18h 09m1 stop Fort Lauderdale

$223Multiple Airlines

Sat, Nov 7 - Mon, Nov 9

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

7h 21m1 stop Denver Intl

7:00 am - 9:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

25h 59m1 stop Fort Lauderdale

$223Multiple Airlines

Recent last minute flight deals from District of Columbia to Chicago

Tue, Oct 13 - Wed, Oct 14

12:30 pm - 7:07 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

7h 37m1 stop Dallas/Fort Worth

8:46 am - 10:17 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

24h 31m1 stop Orlando

$240Frontier

Tue, Oct 13 - Wed, Oct 14

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

18h 24m1 stop Denver Intl

6:30 am - 9:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

14h 29m1 stop Denver Intl

$240Frontier

Tue, Oct 13 - Fri, Nov 13

10:18 pm - 11:32 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 14mnonstop

6:07 pm - 9:10 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 03mnonstop

$438United Airlines

Tue, Oct 13 - Fri, Nov 13

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

2h 00mnonstop

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

1h 50mnonstop

$438Southwest

Tue, Oct 13 - Fri, Nov 13

2:52 pm - 4:15 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 23mnonstop

7:31 pm - 10:29 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 58mnonstop

$438American Airlines

Tue, Oct 13 - Fri, Nov 13

12:20 pm - 3:30 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 10m1 stop Lambert-St Louis

2:10 pm - 4:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$448Southwest

Mon, Oct 12 - Mon, Oct 19

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

18h 24m1 stop Denver Intl

2:55 pm - 9:07 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

29h 12m1 stop Fort Lauderdale

$459Multiple Airlines

Mon, Oct 12 - Mon, Oct 19

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

18h 24m1 stop Denver Intl

2:55 pm - 10:01 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

18h 06m1 stop Fort Lauderdale

$460Multiple Airlines

Mon, Oct 12 - Fri, Oct 16

7:15 pm - 11:00 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

4h 45m1 stop Charlotte Douglas

6:40 pm - 11:58 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

4h 18m1 stop Charlotte Douglas

$474American Airlines

Tue, Oct 13 - Tue, Oct 20

10:18 pm - 11:32 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 14mnonstop

2:37 pm - 5:44 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 07mnonstop

$505United Airlines

Recent direct flight deals from District of Columbia to Chicago

Tue, Nov 3 - Tue, Nov 10

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

2h 10mnonstop

8:35 pm - 11:20 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$211Southwest

Mon, Nov 2 - Wed, Nov 4

10:45 am - 11:50 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

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

1h 45mnonstop

$211Southwest

Wed, Nov 4 - Mon, Nov 9

10:11 am - 11:34 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 23mnonstop

4:51 pm - 7:56 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$211American Airlines

Sat, Nov 7 - Mon, Nov 9

8:39 am - 10:05 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

8:57 pm - 11:55 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 58mnonstop

$211American Airlines

Thu, Nov 5 - Tue, Nov 10

6:25 am - 7:43 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 18mnonstop

9:00 am - 12:03 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 03mnonstop

$211United Airlines

Thu, Dec 3 - Mon, Dec 7

7:41 am - 8:59 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 18mnonstop

5:00 pm - 8:11 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 11mnonstop

$211United Airlines

Tue, Oct 27 - Wed, Oct 28

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

2h 00mnonstop

11:35 am - 2:20 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$211Southwest

Wed, Oct 28 - Wed, Oct 28

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

$211Southwest

Thu, Dec 17 - Sat, Jan 9

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

2h 29mnonstop

5:55 pm - 8:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$211American Airlines

Sat, Nov 7 - Mon, Nov 9

3:37 pm - 5:00 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

$211United Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$96

Best time to beat the crowds with an average 22% drop in price.

Most popular time to fly with an average 17% 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

Schererville

Munster

Porter

Monticello

Saint John

Griffith

More options for your flight to Chicago

Add a hotel or car rental

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

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

Car rentals in Chicago

$96 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

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from District of Columbia 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 District of Columbia

Find direct flights for Chicago

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight