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.

$89 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

Wed, Sep 30 - Tue, Oct 6

7:00 am - 12:23 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

18h 23m1 stop Denver Intl

6:30 am - 12:11 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

28h 41m1 stop Denver Intl

$177Frontier

Mon, Oct 5 - Thu, Oct 8

8:35 pm - 10:00 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 25mnonstop

6:59 am - 10:06 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 07mnonstop

$177American Airlines

Sat, Nov 7 - Mon, Nov 9

6:06 pm - 7:30 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 24mnonstop

12:29 pm - 3:37 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 08mnonstop

$177United Airlines

Wed, Oct 28 - Thu, Oct 29

7:40 am - 9:00 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 20mnonstop

7:00 am - 9:56 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 56mnonstop

$177United Airlines

Thu, Oct 1 - Thu, Oct 1

7:55 am - 8:55 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

11:10 am - 2:00 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Sat, Oct 3 - Mon, Oct 5

9:15 am - 10:15 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

5:00 pm - 7:50 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Tue, Oct 13 - Tue, Oct 20

11:12 am - 7:51 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

21h 39m1 stop Orlando

8:04 am - 8:11 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

11h 07m1 stop Fort Lauderdale

$177Frontier

Sat, Sep 26 - Sat, Sep 26

8:40 am - 10:10 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

8:55 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$177American Airlines

Tue, Sep 22 - Wed, Sep 23

9:40 am - 12:39 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

3h 59m1 stop Detroit Metropolitan Wayne County

1:00 pm - 8:37 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

6h 37m1 stop Atlanta Hartsfield-Jackson

$194Delta

Wed, Sep 23 - Thu, Sep 24

5:35 pm - 8:30 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

3h 55m1 stop Detroit Metropolitan Wayne County

7:05 am - 11:35 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

3h 30m1 stop Detroit Metropolitan Wayne County

$197Delta

Recent last minute flight deals from District of Columbia to Chicago

Fri, Sep 4 - Thu, Sep 17

9:54 pm - 11:08 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

26h 14m1 stop Orlando

11:15 am - 9:32 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

21h 17m1 stop Orlando

$229Frontier

Sun, Sep 6 - Fri, Sep 18

6:20 am - 10:55 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 35m1 stop Atlanta Hartsfield-Jackson

6:25 am - 5:18 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 53m1 stop Atlanta Hartsfield-Jackson

$260Frontier

Sat, Sep 5 - Fri, Oct 2

10:35 am - 11:53 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

6:12 pm - 9:17 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

$362United Airlines

Sat, Sep 5 - Fri, Oct 2

2:44 pm - 4:08 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 24mnonstop

8:55 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$362American Airlines

Sat, Sep 5 - Fri, Oct 2

10:40 am - 11:45 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

8:50 am - 11:35 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$362Southwest

Sat, Sep 5 - Fri, Oct 2

11:56 am - 3:53 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 57m1 stop Charlotte Douglas

6:55 pm - 10:00 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$372American Airlines

Sat, Sep 5 - Fri, Oct 2

10:40 am - 11:45 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

3:50 pm - 9:50 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

5h 00m1 stop Kansas City

$372Southwest

Sat, Sep 5 - Sat, Sep 12

5:15 pm - 6:37 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 22mnonstop

2:30 pm - 5:37 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 07mnonstop

$385United Airlines

Sat, Sep 5 - Wed, Sep 9

11:06 am - 3:44 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 38m1 stop Atlanta Hartsfield-Jackson

11:35 am - 5:11 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

4h 36m1 stop Atlanta Hartsfield-Jackson

$405Delta

Sat, Sep 5 - Wed, Sep 9

6:00 am - 10:10 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 10m1 stop Atlanta Hartsfield-Jackson

11:35 am - 5:11 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

4h 36m1 stop Atlanta Hartsfield-Jackson

$405Delta

Recent direct flight deals from District of Columbia to Chicago

Mon, Oct 5 - Thu, Oct 8

8:35 pm - 10:00 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 25mnonstop

6:59 am - 10:06 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 07mnonstop

$177American Airlines

Sat, Sep 19 - Tue, Sep 22

1:39 pm - 3:05 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

5:54 pm - 9:00 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 06mnonstop

$177American Airlines

Sat, Nov 7 - Mon, Nov 9

6:06 pm - 7:30 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 24mnonstop

12:29 pm - 3:37 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 08mnonstop

$177United Airlines

Wed, Oct 28 - Thu, Oct 29

7:40 am - 9:00 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 20mnonstop

7:00 am - 9:56 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 56mnonstop

$177United Airlines

Sat, Oct 3 - Mon, Oct 5

9:15 am - 10:15 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

5:00 pm - 7:50 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Mon, Oct 5 - Thu, Oct 8

1:05 pm - 2:05 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

$177Southwest

Sat, Sep 26 - Sat, Sep 26

8:40 am - 10:10 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

8:55 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$177American Airlines

Sat, Sep 26 - Sat, Oct 3

3:58 pm - 5:28 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 30mnonstop

6:55 am - 9:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$177American Airlines

Wed, Oct 21 - Thu, Oct 22

3:47 pm - 5:05 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

8:50 am - 11:55 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

$177United Airlines

Sat, Oct 10 - Tue, Oct 13

6:40 pm - 7:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

5:40 am - 8:30 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$177Southwest

Useful Info

Low season	February
High season	October
Cheapest flight	$89

Best time to beat the crowds with an average 20% drop in price.

Most popular time to fly and prices are also 16% lower on average.

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

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Complete your trip

Direct Flights

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Origins

Other airports

Return flight deals

Cabin class types available on flights to District of Columbia

First Class flights to Chicagofrom $468

Business Class flights to Chicagofrom $535

Premium Economy Class flights to Chicagofrom $477

Economy Class flights to Chicagofrom $177

$89 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

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Cheapest flight

FAQs for booking flights from District of Columbia to Chicago

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to District of Columbia

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

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight