How many flights depart from District of Columbia to Chicago on average per day?

The number of flights available between District of Columbia and Chicago is 80 per day as of September 2026. The most frequent departure time is 5:00PM, with 44% of daily flights leaving at noon.

What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from District of Columbia according to our data. United Airlines is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from District of Columbia to Chicago on average per week?

The number of flights available between District of Columbia and Chicago is 565 per week as of September 2026. The most frequent departure day is Thu, with 18% of weekly flights leaving on this day.

What is the cheapest airline that flies from District of Columbia to Chicago?

Frontier, United Airlines, and Southwest are the most popular carriers operating from District of Columbia to Chicago

When did momondo last update prices for flights from District of Columbia to Chicago?

Prices for flights from District of Columbia to Chicago are updated daily.

How many operators does momondo search for flights from District of Columbia to Chicago?

The number of operators available for flights from District of Columbia to Chicago is 5 as of September 2026.

How old do you have to be to fly from District of Columbia to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from District of Columbia to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$90 Cheap Flights from District of Columbia to Chicago in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from District of Columbia to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:50 am - 6:31 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

11h 41m1 stop Atlanta Hartsfield-Jackson

6:00 am - 5:13 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

10h 13m1 stop Atlanta Hartsfield-Jackson

$181Frontier

Wed, Oct 21 - Sat, Oct 24

8:05 am - 12:51 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

5h 46m1 stop Atlanta Hartsfield-Jackson

7:15 am - 5:12 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

8h 57m1 stop Atlanta Hartsfield-Jackson

$181Frontier

Tue, Oct 27 - Sat, Oct 31

8:10 am - 12:28 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

5h 18m1 stop Cincinnati Cinci./N. Kentucky

2:52 pm - 6:04 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 12mnonstop

$186American Airlines

Mon, Nov 23 - Mon, Nov 23

10:39 am - 12:00 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 21mnonstop

1:30 pm - 6:58 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

4h 28m1 stop Detroit Metropolitan Wayne County

$204American Airlines

Tue, Dec 22 - Tue, Dec 22

6:20 pm - 12:01 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

6h 41m1 stop Newark

6:00 pm - 9:11 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 11mnonstop

$233United Airlines

Tue, Nov 3 - Sun, Nov 8

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

25h 00m1 stop Boston Logan Intl

6:30 am - 4:47 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

9h 17m1 stop Denver Intl

$272Multiple Airlines

Tue, Nov 3 - Fri, Nov 6

7:00 am - 12:21 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

18h 21m1 stop Denver Intl

1:00 pm - 11:10 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

21h 10m1 stop Boston Logan Intl

$278Multiple Airlines

Thu, Oct 29 - Wed, Nov 4

10:30 am - 11:51 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 21mnonstop

10:39 am - 4:28 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

4h 49m1 stop Newark

$295United Airlines

Fri, Nov 13 - Sun, Nov 15

2:35 pm - 3:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

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

1h 50mnonstop

$297Southwest

Sat, Dec 5 - Mon, Dec 7

6:50 pm - 8:00 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 10mnonstop

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

1h 45mnonstop

$297Southwest

Sat, Dec 12 - Mon, Dec 14

Cheap last minute flights

Enter your travel dates to find the best prices.

6:00 am - 5:38 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

24h 38m1 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

$299Frontier

Tue, Sep 29 - Wed, Oct 7

7:50 am - 6:23 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

11h 33m1 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

$299Frontier

Wed, Sep 30 - Wed, Oct 7

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

7h 23m1 stop Denver Intl

2:50 pm - 9:59 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

18h 09m1 stop Fort Lauderdale

$405Multiple Airlines

Mon, Sep 28 - Mon, Nov 2

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

2h 00mnonstop

6:00 am - 8:50 amMDW Chicago Midway-DCA Washington, D.C. Reagan-National

1h 50mnonstop

$439Southwest

Thu, Oct 1 - Thu, Oct 15

6:00 pm - 7:00 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

$439Southwest

Thu, Oct 1 - Thu, Oct 15

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

2h 28mnonstop

7:48 am - 10:52 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 04mnonstop

$439American Airlines

Mon, Sep 28 - Mon, Oct 26

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

$439American Airlines

Thu, Oct 1 - Thu, Oct 15

12:30 pm - 7:41 pmIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

8h 11m1 stop Dallas/Fort Worth

3:50 pm - 3:03 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

46h 13m2 stops Orlando Knoxville McGhee Tyson

$462Multiple Airlines

Sat, Sep 26 - Tue, Sep 29

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

3h 57m1 stop Detroit Metropolitan Wayne County

1:27 pm - 6:37 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

4h 10m1 stop Detroit Metropolitan Wayne County

$467Delta

Mon, Sep 28 - Mon, Oct 26

6:00 am - 9:49 amDCA Washington, D.C. Reagan-National-MDW Chicago Midway

4h 49m1 stop Atlanta Hartsfield-Jackson

9:29 am - 4:39 pmMDW Chicago Midway-DCA Washington, D.C. Reagan-National

6h 10m1 stop Detroit Metropolitan Wayne County

$490Delta

Thu, Oct 1 - Thu, Oct 15

Cheap direct flights

Enter your travel dates to find the best prices.

1:06 pm - 2:29 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 23mnonstop

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

2h 04mnonstop

$296American Airlines

Thu, Oct 15 - Mon, Oct 19

2:35 pm - 3:40 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 05mnonstop

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

1h 50mnonstop

$297Southwest

Sat, Dec 5 - Mon, Dec 7

1:05 pm - 2:26 pmDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 21mnonstop

3:00 pm - 6:15 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 15mnonstop

$297United Airlines

Thu, Oct 29 - Wed, Nov 4

6:25 am - 7:43 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 18mnonstop

5:59 am - 8:55 amORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

1h 56mnonstop

$297United Airlines

Thu, Oct 29 - Mon, Nov 2

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

2h 26mnonstop

9:40 am - 12:46 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 06mnonstop

$297American Airlines

Sat, Oct 17 - Mon, Oct 19

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

2h 24mnonstop

5:49 pm - 8:52 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 03mnonstop

$297American Airlines

Sat, Nov 14 - Mon, Nov 16

6:50 pm - 8:00 pmDCA Washington, D.C. Reagan-National-MDW Chicago Midway

2h 10mnonstop

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

1h 45mnonstop

$297Southwest

Sat, Dec 12 - Mon, Dec 14

10:47 pm - 12:01 amIAD Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl

2h 14mnonstop

2:21 pm - 5:24 pmORD Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl

2h 03mnonstop

$297United Airlines

Thu, Nov 5 - Tue, Nov 10

6:35 pm - 7:35 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

$297Southwest

Wed, Oct 14 - Mon, Oct 19

10:13 am - 11:36 amDCA Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl

2h 23mnonstop

4:51 pm - 7:56 pmORD Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National

2h 05mnonstop

$297American Airlines

Thu, Oct 29 - Mon, Nov 2

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Frontier flights from District of Columbia to Chicago

Our best Frontier deals on District of Columbia to Chicago flight tickets

Frontier

Oct 21

IAD7:50 amWashington, D.C. Dulles Intl

11h 41m

1 stop

ORD6:31 pmChicago O'Hare Intl

Oct 28

ORD7:15 amChicago O'Hare Intl

8h 57m

1 stop

IAD5:12 pmWashington, D.C. Dulles Intl

$181

Frontier

Oct 21

IAD7:50 amWashington, D.C. Dulles Intl

11h 41m

1 stop

ORD6:31 pmChicago O'Hare Intl

Oct 27

ORD7:15 amChicago O'Hare Intl

8h 57m

1 stop

IAD5:12 pmWashington, D.C. Dulles Intl

$183

Frontier

Oct 6

IAD6:13 pmWashington, D.C. Dulles Intl

22h 07m

1 stop

ORD3:20 pmChicago O'Hare Intl

Oct 28

ORD7:15 amChicago O'Hare Intl

8h 57m

1 stop

IAD5:12 pmWashington, D.C. Dulles Intl

$187

American Airlines flights from District of Columbia to Chicago

Our best American Airlines deals on District of Columbia to Chicago flight tickets

American Airlines

Nov 23

DCA8:10 amWashington, D.C. Reagan-National

5h 18m

1 stop

ORD12:28 pmChicago O'Hare Intl

Nov 23

ORD2:52 pmChicago O'Hare Intl

2h 12m

DCA6:04 pmWashington, D.C. Reagan-National

$186

American Airlines

Dec 22

DCA10:39 amWashington, D.C. Reagan-National

2h 21m

ORD12:00 pmChicago O'Hare Intl

Dec 22

ORD1:30 pmChicago O'Hare Intl

4h 28m

1 stop

DCA6:58 pmWashington, D.C. Reagan-National

$204

American Airlines

Oct 6

DCA7:18 pmWashington, D.C. Reagan-National

4h 42m

1 stop

ORD11:00 pmChicago O'Hare Intl

Oct 13

ORD10:20 amChicago O'Hare Intl

2h 06m

DCA1:26 pmWashington, D.C. Reagan-National

$405

momondo Fare Finder

Use the filters below to find and compare flights from District of Columbia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Wed 10/21

7:50 am-6:31 pm

1 stop11h 41m

Chicago O'Hare Intl

Sat 10/24

6:00 am-5:13 pm

1 stop10h 13m

$181

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Tue 10/27

8:05 am-12:51 pm

1 stop5h 46m

Chicago O'Hare Intl

Sat 10/31

7:15 am-5:12 pm

1 stop8h 57m

$181

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Mon 11/23

8:10 am-12:28 pm

1 stop5h 18m

Chicago O'Hare Intl

Mon 11/23

2:52 pm-6:04 pm

Nonstop2h 12m

$186

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Tue 12/22

10:39 am-12:00 pm

Nonstop2h 21m

Chicago O'Hare Intl

Tue 12/22

1:30 pm-6:58 pm

1 stop4h 28m

$204

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Tue 11/3

6:20 pm-12:01 am

1 stop6h 41m

Chicago O'Hare Intl

Sun 11/8

6:00 pm-9:11 pm

Nonstop2h 11m

$233

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Tue 11/3

12:00 pm-12:00 pm

1 stop25h 00m

Chicago O'Hare Intl

Fri 11/6

6:30 am-4:47 pm

1 stop9h 17m

$272

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Thu 10/29

7:00 am-12:21 am

1 stop18h 21m

Chicago O'Hare Intl

Wed 11/4

1:00 pm-11:10 am

1 stop21h 10m

$278

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl

DCAORD

Washington, D.C. Reagan-National

Fri 11/13

10:30 am-11:51 am

Nonstop2h 21m

Chicago O'Hare Intl

Sun 11/15

10:39 am-4:28 pm

1 stop4h 49m

$295

Quickest round-trip

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Sat 12/5

2:35 pm-3:40 pm

Nonstop2h 05m

Chicago Midway

Mon 12/7

12:05 pm-2:55 pm

Nonstop1h 50m

$297

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Sat 12/12

6:50 pm-8:00 pm

Nonstop2h 10m

Chicago Midway

Mon 12/14

8:35 pm-11:20 pm

Nonstop1h 45m

$297

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from District of Columbia to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from District of Columbia, with most prices found around $293. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from District of Columbia to Chicago during February average around $300.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $408. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from District of Columbia to Chicago for around $530.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from District of Columbia to Chicago during this time can be as low as $424. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $465.

What is the cheapest District of Columbia to Chicago flight route?

Fly from Baltimore/Washington to Chicago O'Hare Intl for the best District of Columbia - Chicago flight prices

How far in advance should I book a flight from District of Columbia to Chicago?

You are more likely to see cheaper flights to Chicago from District of Columbia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $404 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from District of Columbia for as low as $302 on momondo.

What cabin class options are available on District of Columbia to Chicago flights?

There are 4 cabin classes available to choose from on District of Columbia to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on District of Columbia to Chicago flights?

No. A direct flight is the cheapest option for a flight between District of Columbia to Chicago.

Cheap District of Columbia to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from District of Columbia to Chicago

Best Price Found	$90
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from District of Columbia in the past 72 hours is $90. The best round-trip flight deal from District of Columbia to Chicago found on momondo in the last 72 hours is $181.

The fastest flight from District of Columbia to Chicago takes 1h 55m

Direct flights go from District of Columbia to Chicago every day.

There are 3 airports in Chicago. From District of Columbia there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from District of Columbia to Chicago

When did momondo last update prices for flights from District of Columbia to Chicago?
Prices for flights from District of Columbia to Chicago are updated daily.
How many operators does momondo search for flights from District of Columbia to Chicago?
The number of operators available for flights from District of Columbia to Chicago is 5 as of September 2026.
How old do you have to be to fly from District of Columbia to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from District of Columbia to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from District of Columbia to Chicago?
Based on momondo bookings for flights between District of Columbia and Chicago, the leading plane model is Boeing 737 MAX 8, making up 14.40% of the total bookings. Other popular models include Boeing 737-800 with 12.36%, Airbus A320-100/200 with 10.85%, and Airbus A319 with 10.51%.

Best airlines flying from District of Columbia to Chicago

Compare and see reviews for airlines that fly from District of Columbia to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $29	Free Cancellation	Rating 5.6 2,577 reviews	Search Frontier flights
Delta	PriceFrom $149	Free Cancellation	Rating 7.8 8,598 reviews	Search Delta flights
United Airlines	PriceFrom $176	Free Cancellation	Rating 7.4 10,236 reviews	Search United Airlines flights
Southwest	PriceFrom $179	Free Cancellation	Rating 8.0 4,200 reviews	Search Southwest flights
American Airlines	PriceFrom $186	Free Cancellation	Rating 7.0 12,085 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from District of Columbia to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from District of Columbia to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from District of Columbia to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from District of Columbia with this policy.

How can momondo help me find flights from District of Columbia to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from District of Columbia to Chicago.

I’m not ready to book a flight from District of Columbia to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for District of Columbia to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Sun 10/25

Sun 11/1

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from District of Columbia

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from District of Columbia to Chicago from $90

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from District of Columbia to Chicago departing on 10/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from District of Columbia to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Frontier flights from District of Columbia to Chicago

Our best Frontier deals on District of Columbia to Chicago flight tickets

American Airlines flights from District of Columbia to Chicago

Our best American Airlines deals on District of Columbia to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from District of Columbia to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from District of Columbia to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest District of Columbia to Chicago flight route?

How far in advance should I book a flight from District of Columbia to Chicago?

What cabin class options are available on District of Columbia to Chicago flights?

Can stopping save me money on District of Columbia to Chicago flights?

What is the cheapest airline that flies from District of Columbia to Chicago?

What airlines fly to Chicago?

How many flights depart from District of Columbia to Chicago on average per day?

How many flights depart from District of Columbia to Chicago on average per week?

Cheap District of Columbia to Chicago flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from District of Columbia to Chicago

Best airlines flying from District of Columbia to Chicago

Compare and see reviews for airlines that fly from District of Columbia to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from District of Columbia

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year