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

Sun, Sep 6 - Sat, Sep 12

11:50 am - 12:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

1h 55mnonstop

11:15 am - 2:05 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$184Southwest

Sat, Sep 12 - Mon, Sep 14

6:00 pm - 12:23 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

7h 23m1 stop Denver Intl

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

14h 29m1 stop Denver Intl

$184Frontier

Sat, Sep 5 - Tue, Sep 8

10:16 pm - 11:37 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 21mnonstop

9:56 am - 12:57 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 01mnonstop

$184American Airlines

Wed, Sep 2 - Sat, Sep 5

5:23 pm - 6:54 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 31mnonstop

6:00 am - 9:16 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 16mnonstop

$184American Airlines

Fri, Oct 30 - Mon, Nov 2

9:30 am - 10:50 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 20mnonstop

6:00 am - 8:56 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 56mnonstop

$184United Airlines

Fri, Sep 11 - Mon, Sep 14

9:30 am - 10:47 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 17mnonstop

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

1h 59mnonstop

$184United Airlines

Tue, Sep 29 - Fri, Oct 30

6:00 am - 12:05 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

7h 05m2 stops Orlando Atlanta Hartsfield-Jackson

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

1h 50mnonstop

$185Southwest

Sun, Sep 6 - Fri, Sep 11

8:39 pm - 7:53 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

12h 14m1 stop Atlanta Hartsfield-Jackson

8:55 am - 4:30 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

6h 35m1 stop Detroit Metropolitan Wayne County

$185Frontier

Sun, Sep 6 - Fri, Sep 11

6:10 am - 9:17 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 07m1 stop Detroit Metropolitan Wayne County

4:30 pm - 10:40 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

5h 10m1 stop Atlanta Hartsfield-Jackson

$197Delta

Sun, Sep 6 - Fri, Sep 11

12:33 pm - 4:59 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

5h 26m1 stop Detroit Metropolitan Wayne County

11:35 am - 6:28 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

5h 53m1 stop Atlanta Hartsfield-Jackson

$197Delta

Recent last minute flight deals from District of Columbia to Chicago

Fri, Aug 14 - Wed, Sep 16

8:33 pm - 8:02 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

12h 29m1 stop Atlanta Hartsfield-Jackson

7:11 am - 8:09 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

11h 58m1 stop Fort Lauderdale

$260Frontier

Sun, Aug 16 - Mon, Sep 21

8:33 pm - 8:02 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

12h 29m1 stop Atlanta Hartsfield-Jackson

10:26 am - 5:18 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

5h 52m1 stop Atlanta Hartsfield-Jackson

$260Frontier

Mon, Aug 17 - Mon, Sep 21

2:00 pm - 3:16 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 16mnonstop

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

1h 59mnonstop

$356United Airlines

Fri, Aug 14 - Mon, Sep 21

1:04 pm - 2:21 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 17mnonstop

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

1h 59mnonstop

$356United Airlines

Mon, Aug 17 - Mon, Sep 21

12:57 pm - 4:48 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 51m1 stop Charlotte Douglas

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

2h 06mnonstop

$366American Airlines

Fri, Aug 14 - Mon, Sep 21

12:57 pm - 4:48 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 51m1 stop Charlotte Douglas

7:47 am - 10:52 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$366American Airlines

Mon, Aug 17 - Mon, Aug 24

6:00 pm - 1:36 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

20h 36m1 stop Denver Intl

2:35 pm - 11:32 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

7h 57m1 stop Fort Lauderdale

$369Multiple Airlines

Fri, Aug 14 - Mon, Aug 24

7:00 am - 8:52 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

14h 52m1 stop Denver Intl

2:35 pm - 11:32 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

7h 57m1 stop Fort Lauderdale

$389Multiple Airlines

Mon, Aug 17 - Sat, Aug 29

5:47 pm - 10:36 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 49m1 stop Atlanta Hartsfield-Jackson

6:42 pm - 11:26 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

3h 44m1 stop Detroit Metropolitan Wayne County

$408Delta

Sat, Aug 15 - Sat, Aug 22

5:47 pm - 10:36 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

5h 49m1 stop Atlanta Hartsfield-Jackson

6:42 pm - 11:26 pmMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

3h 44m1 stop Detroit Metropolitan Wayne County

$473Delta

Recent direct flight deals from District of Columbia to Chicago

Sun, Sep 6 - Sat, Sep 12

9:07 am - 10:30 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 23mnonstop

8:50 am - 11:54 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$184American Airlines

Wed, Sep 2 - Sat, Sep 5

5:23 pm - 6:54 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 31mnonstop

6:00 am - 9:16 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 16mnonstop

$184American Airlines

Fri, Oct 30 - Mon, Nov 2

9:30 am - 10:50 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 20mnonstop

6:00 am - 8:56 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 56mnonstop

$184United Airlines

Wed, Oct 28 - Fri, Oct 30

8:30 am - 9:50 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 20mnonstop

9:00 am - 12:05 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$184United Airlines

Sun, Sep 6 - Sat, Sep 12

11:50 am - 12:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

1h 55mnonstop

11:15 am - 2:05 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$184Southwest

Fri, Sep 11 - Mon, Sep 14

6:30 am - 7:58 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 28mnonstop

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

2h 04mnonstop

$184American Airlines

Tue, Sep 1 - Sat, Sep 5

11:35 am - 12:54 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 19mnonstop

8:00 am - 10:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 59mnonstop

$184American Airlines

Wed, Oct 28 - Fri, Oct 30

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

2h 19mnonstop

1:15 pm - 4:18 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 03mnonstop

$184United Airlines

Sat, Sep 26 - Tue, Sep 29

6:40 pm - 7:40 pmDCA 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

$191Southwest

Thu, Sep 17 - Mon, Sep 21

9:15 pm - 10:15 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

9:00 pm - 11:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 55mnonstop

$191Southwest

Useful Info

Low season	February
High season	October
Cheapest flight	$89

Best time to beat the crowds with an average 19% drop in price.

Most popular time to fly and prices are also 18% 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

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Complete your trip

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Flights to other cities

Origins

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Return flight deals

Cabin class types available on flights to District of Columbia

First Class flights to Chicagofrom $477

Business Class flights to Chicagofrom $501

Premium Economy Class flights to Chicagofrom $485

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