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 74 per day as of April 2026. The most frequent departure time is 11:00AM, with 47% of daily flights leaving at noon.

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

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

What airlines fly to Chicago?

United Airlines, American Airlines and Frontier 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 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 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 518 per week as of April 2026. The most frequent departure day is Sun, with 18% of weekly flights leaving on this day.

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 April 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.

$108 Cheap Flights from District of Columbia to Chicago in 2026

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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.

5:26 pm - 10:02 pm

IAD

MDW

5h 36m

1 stop

9:14 am - 5:28 pm

MDW

IAD

7h 14m

1 stop

$219Multiple Airlines

Sat, May 9 - Thu, May 21

6:10 am - 11:32 am

IAD

ORD

6h 22m

1 stop

4:05 pm - 5:27 pm

ORD

IAD

24h 22m

2 stops

$220Frontier

Thu, Apr 30 - Tue, May 5

11:07 am - 10:02 pm

IAD

MDW

11h 55m

1 stop

6:00 am - 4:21 pm

MDW

IAD

9h 21m

1 stop

$220Frontier

Thu, May 28 - Tue, Jun 2

6:49 am - 7:51 pm

IAD

ORD

14h 02m

1 stop

7:33 pm - 5:27 pm

ORD

IAD

20h 54m

2 stops

$221Multiple Airlines

Sat, May 16 - Thu, May 21

7:59 am - 9:45 am

DCA

ORD

26h 46m

1 stop

9:37 pm - 12:59 pm

ORD

DCA

14h 22m

1 stop

$221Frontier

Sat, May 2 - Wed, May 6

2:40 pm - 9:45 pm

DCA

MDW

8h 05m

2 stops

5:00 pm - 7:55 pm

MDW

DCA

1h 55mnonstop

$223Southwest

Tue, May 5 - Thu, May 7

8:00 am - 4:45 pm

DCA

MDW

9h 45m

1 stop

6:05 am - 8:55 am

MDW

DCA

1h 50mnonstop

$224Southwest

Sat, May 16 - Tue, May 19

6:00 pm - 10:28 pm

DCA

MDW

5h 28m

1 stop

1:24 pm - 6:59 pm

MDW

DCA

4h 35m

1 stop

$226Delta

Wed, Apr 29 - Wed, May 6

7:00 pm - 8:22 pm

DCA

ORD

2h 22mnonstop

4:00 pm - 7:10 pm

ORD

DCA

2h 10mnonstop

$227United Airlines

Sat, May 23 - Tue, May 26

7:38 pm - 11:59 pm

IAD

ORD

5h 21m

1 stop

9:25 am - 4:31 pm

ORD

IAD

6h 06m

1 stop

$228Delta

Mon, May 11 - Tue, May 19

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United Airlines flights from District of Columbia to Chicago

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

United Airlines

May 23

DCA7:00 pmWashington, D.C. Reagan-National

2h 22m

ORD8:22 pmChicago O'Hare Intl

May 26

ORD4:00 pmChicago O'Hare Intl

2h 10m

DCA7:10 pmWashington, D.C. Reagan-National

$227

United Airlines

Jul 1

DCA7:30 amWashington, D.C. Reagan-National

2h 17m

ORD8:47 amChicago O'Hare Intl

Jul 4

ORD7:00 amChicago O'Hare Intl

1h 59m

DCA9:59 amWashington, D.C. Reagan-National

$233

United Airlines

May 23

DCA5:00 pmWashington, D.C. Reagan-National

2h 22m

ORD6:22 pmChicago O'Hare Intl

Jun 1

ORD6:00 amChicago O'Hare Intl

1h 54m

DCA8:54 amWashington, D.C. Reagan-National

$239

JetBlue flights from District of Columbia to Chicago

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

JetBlue

May 6

DCA3:35 pmWashington, D.C. Reagan-National

6h 18m

1 stop

ORD8:53 pmChicago O'Hare Intl

May 12

ORD9:49 amChicago O'Hare Intl

6h 57m

1 stop

DCA5:46 pmWashington, D.C. Reagan-National

$251

JetBlue

Apr 28

DCA3:35 pmWashington, D.C. Reagan-National

7h 04m

1 stop

ORD9:39 pmChicago O'Hare Intl

May 1

ORD9:49 amChicago O'Hare Intl

5h 53m

1 stop

DCA4:42 pmWashington, D.C. Reagan-National

$365

JetBlue

Apr 27

DCA6:00 amWashington, D.C. Reagan-National

26h 41m

1 stop

ORD7:41 amChicago O'Hare Intl

Apr 30

ORD9:49 amChicago O'Hare Intl

5h 53m

1 stop

DCA4:42 pmWashington, D.C. Reagan-National

$393

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 - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/9

5:26 pm-10:02 pm

1 stop5h 36m

Chicago Midway

Thu 5/21

9:14 am-5:28 pm

1 stop7h 14m

$219

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 4/30

6:10 am-11:32 am

1 stop6h 22m

Chicago O'Hare Intl

Tue 5/5

4:05 pm-5:27 pm

2 stops24h 22m

$220

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/28

11:07 am-10:02 pm

1 stop11h 55m

Chicago Midway

Tue 6/2

6:00 am-4:21 pm

1 stop9h 21m

$220

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/16

6:49 am-7:51 pm

1 stop14h 02m

Chicago O'Hare Intl

Thu 5/21

7:33 pm-5:27 pm

2 stops20h 54m

$221

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/2

7:59 am-9:45 am

1 stop26h 46m

Chicago O'Hare Intl

Wed 5/6

9:37 pm-12:59 pm

1 stop14h 22m

$221

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 5/5

2:40 pm-9:45 pm

2 stops8h 05m

Chicago Midway

Thu 5/7

5:00 pm-7:55 pm

Nonstop1h 55m

$223

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/16

8:00 am-4:45 pm

1 stop9h 45m

Chicago Midway

Tue 5/19

6:05 am-8:55 am

Nonstop1h 50m

$224

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/29

6:00 pm-10:28 pm

1 stop5h 28m

Chicago Midway

Wed 5/6

1:24 pm-6:59 pm

1 stop4h 35m

$226

Quickest round-trip

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/23

7:00 pm-8:22 pm

Nonstop2h 22m

Chicago O'Hare Intl

Tue 5/26

4:00 pm-7:10 pm

Nonstop2h 10m

$227

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 5/11

7:38 pm-11:59 pm

1 stop5h 21m

Chicago O'Hare Intl

Tue 5/19

9:25 am-4:31 pm

1 stop6h 06m

$228

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 September is, on average, the cheapest month to fly to Chicago from District of Columbia, with most prices found around $203. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from District of Columbia to Chicago during August average around $218.

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 Friday when prices can be found for as low as $386. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from District of Columbia to Chicago for around $512.

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 $378. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $424.

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

Fly from Washington, D.C. Reagan-National to Chicago Midway for the best District of Columbia - Chicago flight prices

How far in advance should I book a flight 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 $370 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 $201 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?

You could potentially save up to 6% on your flight if you consider stops on a District of Columbia to Chicago flight.

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	$195
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 $195. The best round-trip flight deal from District of Columbia to Chicago found on momondo in the last 72 hours is $303.

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 April 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 14.33% of the total bookings. Other popular models include Boeing 737-800 with 13.58%, Airbus A319 with 13.48%, and Boeing 737-900 with 8.75%.

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
Spirit Airlines	PriceFrom $52	Free Cancellation	Rating 6.3 8,626 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $57	Free Cancellation	Rating 5.7 2,987 reviews	Search Frontier flights
Southwest	PriceFrom $134	Free Cancellation	Rating 8.0 4,328 reviews	Search Southwest flights
Delta	PriceFrom $149	Free Cancellation	Rating 7.9 8,422 reviews	Search Delta flights
United Airlines	PriceFrom $152	Free Cancellation	Rating 7.4 9,605 reviews	Search United Airlines flights
American Airlines	PriceFrom $158	Free Cancellation	Rating 7.1 11,617 reviews	Search American Airlines flights

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New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

Crown Point

Chesterton

Monticello

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.

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Fly into one of these airports located in Chicago

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Cheap flights from District of Columbia to Chicago from $108

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 4/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from District of Columbia to Chicago

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

JetBlue flights from District of Columbia to Chicago

Our best JetBlue 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 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

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

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

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