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

Save 21% 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

Tue, Sep 8 - Fri, Sep 11

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

$181Frontier

Fri, Oct 2 - Tue, Oct 6

7:50 am - 5:51 pmIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

11h 01m1 stop Atlanta Hartsfield-Jackson

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

9h 53m1 stop Atlanta Hartsfield-Jackson

$182Frontier

Wed, Nov 18 - Wed, Nov 18

2:40 pm - 5:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 05m1 stop Lambert-St Louis

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

1h 45mnonstop

$183Southwest

Mon, Nov 16 - Wed, Nov 18

2:40 pm - 5:45 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 05m1 stop Lambert-St Louis

12:05 pm - 2:55 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$183Southwest

Tue, Sep 15 - Sat, Sep 26

9:04 pm - 11:51 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

15h 47m1 stop Atlanta Hartsfield-Jackson

7:11 am - 6:33 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

10h 22m2 stops Fort Lauderdale Tampa

$194Multiple Airlines

Sat, Sep 12 - Sat, Sep 19

6:32 pm - 10:44 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

5h 12m1 stop Atlanta Hartsfield-Jackson

6:40 pm - 11:02 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

3h 22m1 stop Detroit Metropolitan Wayne County

$197Delta

Wed, Oct 7 - Sat, Oct 10

12:27 pm - 6:00 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

6h 33m1 stop Detroit Metropolitan Wayne County

6:44 pm - 11:07 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

3h 23m1 stop Detroit Metropolitan Wayne County

$197Delta

Sat, Sep 12 - Sat, Sep 19

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

2h 30mnonstop

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

2h 05mnonstop

$197American Airlines

Thu, Oct 15 - Mon, Oct 19

7:45 am - 9:11 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

5:59 am - 9:14 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 15mnonstop

$197American Airlines

Sun, Nov 22 - Wed, Dec 2

8:32 pm - 8:39 amIAD Washington, D.C. Dulles Intl-MDW Chicago Midway

13h 07m1 stop Knoxville McGhee Tyson

9:23 pm - 7:51 amMDW Chicago Midway-IAD Washington, D.C. Dulles Intl

9h 28m1 stop Atlanta Hartsfield-Jackson

$266Multiple Airlines

Recent last minute flight deals from District of Columbia to Chicago

Sun, Aug 23 - Mon, Sep 21

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

12h 14m1 stop Atlanta Hartsfield-Jackson

8:55 pm - 6:20 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

32h 25m1 stop Las Vegas Harry Reid Intl

$249Frontier

Fri, Aug 21 - Wed, Sep 23

8:59 am - 7:02 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

11h 03m1 stop Las Vegas Harry Reid Intl

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

11h 58m1 stop Fort Lauderdale

$259Frontier

Sun, Aug 23 - Mon, Sep 21

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

2h 18mnonstop

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

1h 58mnonstop

$349United Airlines

Fri, Aug 21 - Mon, Sep 21

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

2h 22mnonstop

9:39 pm - 12:44 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

$349United Airlines

Sun, Aug 23 - Mon, Sep 21

9:30 am - 10:25 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

1h 55mnonstop

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

1h 55mnonstop

$349Southwest

Fri, Aug 21 - Mon, Sep 21

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

1h 55mnonstop

5:45 am - 8:30 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$349Southwest

Fri, Aug 21 - Wed, Sep 23

12:00 pm - 11:08 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

12h 08m2 stops Blountville Tri Cities TN/VA Orlando

6:00 am - 3:34 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

8h 34m1 stop Dallas/Fort Worth

$352Multiple Airlines

Sun, Aug 23 - Mon, Sep 21

4:59 pm - 8:44 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 45m1 stop Columbus

6:00 am - 9:20 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 20mnonstop

$359American Airlines

Mon, Aug 24 - Tue, Sep 22

5:34 pm - 11:52 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

7h 18m1 stop Charlotte Douglas

1:19 pm - 6:59 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

4h 40m1 stop Charlotte Douglas

$374American Airlines

Sat, Aug 22 - Tue, Aug 25

7:00 am - 1:36 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

7h 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

$415Multiple Airlines

Recent direct flight deals from District of Columbia to Chicago

Sat, Sep 12 - Sat, Sep 19

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

2h 30mnonstop

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

2h 05mnonstop

$197American Airlines

Thu, Oct 15 - Mon, Oct 19

7:45 am - 9:11 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

5:59 am - 9:14 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 15mnonstop

$197American Airlines

Wed, Sep 9 - Sat, Sep 12

5:00 pm - 6:29 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 29mnonstop

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

2h 04mnonstop

$197American Airlines

Sat, Oct 31 - Tue, Nov 3

7:45 am - 9:11 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 26mnonstop

8:57 pm - 11:59 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 02mnonstop

$197American Airlines

Sat, Oct 10 - Mon, Oct 12

10:18 pm - 11:31 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 13mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$198United Airlines

Thu, Oct 8 - Mon, Oct 12

6:10 am - 7:25 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$200United Airlines

Wed, Oct 7 - Mon, Oct 12

6:10 am - 7:25 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 15mnonstop

9:52 pm - 12:58 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 06mnonstop

$200United Airlines

Fri, Dec 4 - Sat, Dec 5

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

2h 10mnonstop

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

1h 55mnonstop

$216Southwest

Fri, Sep 18 - Mon, Sep 21

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

2h 00mnonstop

5:45 am - 8:30 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 45mnonstop

$216Southwest

Tue, Oct 6 - Fri, Oct 9

1:00 pm - 2:00 pmDCA 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

$216Southwest

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 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

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

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 $477

Business Class flights to Chicagofrom $477

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

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