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 16 - Sat, Sep 19

3:15 pm - 4:29 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 14mnonstop

7:32 pm - 6:20 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

9h 48m1 stop Las Vegas Harry Reid Intl

$178Frontier

Sat, Oct 10 - Sat, Oct 17

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

2h 25mnonstop

7:55 am - 10:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$178American Airlines

Thu, Oct 1 - Sat, Oct 31

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

2h 29mnonstop

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

2h 07mnonstop

$178American Airlines

Mon, Sep 28 - Wed, Sep 30

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

18h 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

$182Frontier

Wed, Nov 11 - Sat, Nov 14

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

4h 05m1 stop Lambert-St Louis

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

1h 50mnonstop

$183Southwest

Tue, Dec 1 - Mon, Dec 7

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 29 - Sat, Oct 3

6:10 am - 9:07 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

3h 57m1 stop Detroit Metropolitan Wayne County

4:30 pm - 11:44 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

6h 14m1 stop Atlanta Hartsfield-Jackson

$184Delta

Sat, Sep 26 - Wed, Sep 30

6:10 am - 9:07 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

3h 57m1 stop Detroit Metropolitan Wayne County

5:11 pm - 11:44 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

5h 33m1 stop Atlanta Hartsfield-Jackson

$197Delta

Mon, Sep 28 - Mon, Sep 28

8:20 am - 9:38 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

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

2h 06mnonstop

$199United Airlines

Thu, Oct 8 - Mon, Oct 12

1:10 pm - 2:26 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 16mnonstop

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

2h 06mnonstop

$201United Airlines

Recent last minute flight deals from District of Columbia to Chicago

Fri, Aug 28 - Mon, Sep 28

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

$249Frontier

Fri, Aug 28 - Mon, Sep 28

10:45 am - 11:08 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

13h 23m1 stop Orlando

3:50 pm - 10:17 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

17h 27m1 stop Orlando

$249Frontier

Fri, Aug 28 - Mon, Sep 28

9:10 am - 10:10 amDCA 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

$325Southwest

Fri, Aug 28 - Mon, Sep 28

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

2h 31mnonstop

5:00 pm - 8:06 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 06mnonstop

$325American Airlines

Fri, Aug 28 - Mon, Sep 28

5:05 pm - 10:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

6h 35m1 stop Orlando

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

1h 55mnonstop

$335Southwest

Fri, Aug 28 - Mon, Sep 28

8:32 am - 12:15 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

4h 43m1 stop Charlotte Douglas

10:35 am - 1:38 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 03mnonstop

$335American Airlines

Mon, Aug 31 - Sat, Sep 12

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

6:20 am - 5:18 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

9h 58m1 stop Atlanta Hartsfield-Jackson

$372Multiple Airlines

Mon, Aug 31 - Tue, Sep 8

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

1:59 pm - 10:52 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

7h 53m1 stop Atlanta Hartsfield-Jackson

$380Multiple Airlines

Fri, Aug 28 - Mon, Sep 28

10:27 pm - 11:40 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 13mnonstop

6:06 pm - 9:11 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 05mnonstop

$399United Airlines

Sat, Aug 29 - Sat, Aug 29

3:40 pm - 4:59 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 19mnonstop

7:38 pm - 7:26 amORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

10h 48m1 stop Indianapolis

$429United Airlines

Recent direct flight deals from District of Columbia to Chicago

Sat, Oct 10 - Sat, Oct 17

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

2h 25mnonstop

7:55 am - 10:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$178American Airlines

Thu, Oct 1 - Sat, Oct 31

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

2h 29mnonstop

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

2h 07mnonstop

$178American Airlines

Thu, Sep 17 - Mon, Sep 21

3:58 pm - 5:28 pmDCA 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

$178American Airlines

Thu, Sep 24 - Mon, Sep 28

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

2h 28mnonstop

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

2h 05mnonstop

$178American Airlines

Mon, Sep 28 - Mon, Sep 28

8:20 am - 9:38 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 18mnonstop

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

2h 06mnonstop

$199United Airlines

Thu, Oct 8 - Mon, Oct 12

1:10 pm - 2:26 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 16mnonstop

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

2h 06mnonstop

$201United 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

$201United Airlines

Fri, Oct 16 - Sat, Oct 17

8:40 pm - 9:40 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

$216Southwest

Thu, Sep 17 - Sat, Sep 19

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

2h 00mnonstop

5:10 pm - 8:05 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 55mnonstop

$216Southwest

Fri, Oct 16 - Tue, Oct 20

8:40 pm - 9:40 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

$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 17% 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

Schererville

Chesterton

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

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 $573

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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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