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

Sat, Sep 5 - Sun, Sep 6

3:55 pm - 7:20 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 25m1 stop Nashville Intl

11:05 am - 1:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$187Southwest

Sun, Sep 6 - Fri, Sep 11

9:00 pm - 10:05 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

3:20 pm - 10:30 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

6h 10m1 stop Nashville Intl

$187Southwest

Tue, Sep 8 - Wed, Sep 9

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

$189Frontier

Sat, Sep 5 - Sat, Sep 19

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

20h 36m1 stop Denver Intl

6:30 am - 4:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

9h 29m1 stop Denver Intl

$190Frontier

Sat, Sep 5 - Sun, Sep 6

6:30 pm - 11:57 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 27m1 stop Atlanta Hartsfield-Jackson

6:40 am - 12:45 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

5h 05m1 stop Atlanta Hartsfield-Jackson

$197Delta

Sat, Sep 5 - Sun, Sep 6

6:30 pm - 11:57 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 27m1 stop Atlanta Hartsfield-Jackson

6:40 am - 12:45 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

5h 05m1 stop Atlanta Hartsfield-Jackson

$197Delta

Sat, Sep 5 - Tue, Sep 8

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

2h 19mnonstop

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

2h 01mnonstop

$216American Airlines

Thu, Sep 3 - Sun, Sep 6

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

2h 23mnonstop

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

2h 16mnonstop

$216American Airlines

Thu, Sep 3 - Sun, Sep 6

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

$216United Airlines

Thu, Sep 3 - Sun, Sep 6

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

$216United Airlines

Recent last minute flight deals from District of Columbia to Chicago

Sun, Aug 9 - Thu, Sep 10

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

$268Frontier

Fri, Aug 7 - Wed, Sep 23

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

$268Frontier

Tue, Aug 11 - Sat, Aug 15

1:46 pm - 3:10 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 24mnonstop

10:53 am - 1:54 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 01mnonstop

$291American Airlines

Tue, Aug 11 - Sat, Aug 15

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

4h 51m1 stop Charlotte Douglas

1:25 pm - 4:29 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$301American Airlines

Sun, Aug 9 - Thu, Sep 10

3:35 pm - 4:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

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

1h 55mnonstop

$388Southwest

Sun, Aug 9 - Thu, Sep 10

3:35 pm - 4:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

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

1h 55mnonstop

$388Southwest

Sun, Aug 9 - Thu, Sep 10

10:30 am - 11:49 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 19mnonstop

6:25 am - 9:23 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

1h 58mnonstop

$388United Airlines

Fri, Aug 7 - Wed, Sep 23

5:42 pm - 6:50 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 08mnonstop

10:50 am - 1:55 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

$388United Airlines

Sun, Aug 9 - Thu, Sep 10

6:10 am - 9:17 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

4h 07m1 stop Detroit Metropolitan Wayne County

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

4h 36m1 stop Atlanta Hartsfield-Jackson

$408Delta

Sun, Aug 9 - Thu, Sep 10

6:10 am - 9:17 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

4h 07m1 stop Detroit Metropolitan Wayne County

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

4h 36m1 stop Atlanta Hartsfield-Jackson

$408Delta

Recent direct flight deals from District of Columbia to Chicago

Thu, Sep 3 - Sun, Sep 6

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

$216United Airlines

Fri, Sep 11 - Sat, Sep 12

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

$216United Airlines

Sat, Sep 5 - Tue, Sep 8

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

2h 19mnonstop

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

2h 01mnonstop

$216American Airlines

Thu, Sep 10 - Fri, Sep 11

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

2h 24mnonstop

9:53 am - 12:58 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$216American Airlines

Fri, Oct 30 - Tue, Nov 3

8:00 am - 9:00 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 00mnonstop

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

1h 45mnonstop

$216Southwest

Sat, Sep 5 - Sat, Sep 12

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

2h 00mnonstop

8:05 am - 11:05 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

2h 00mnonstop

$216Southwest

Sun, Sep 6 - Tue, Sep 8

6:30 am - 7:44 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 14mnonstop

7:59 am - 10:57 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 58mnonstop

$216United Airlines

Wed, Sep 2 - Sun, Sep 6

6:30 am - 7:44 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 14mnonstop

8:00 am - 11:01 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 01mnonstop

$216United Airlines

Fri, Sep 11 - Mon, Sep 14

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

$216Southwest

Thu, Sep 10 - Fri, Sep 11

7:25 am - 8:20 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

1h 55mnonstop

4:55 pm - 7:50 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 55mnonstop

$216Southwest

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 19% 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.

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to District of Columbia

First Class flights to Chicagofrom $543

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

Low season

High season

Cheapest flight

FAQs for booking flights from District of Columbia to 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