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 48 per day as of August 2025. The most frequent departure time is 6:00AM, with 43% of daily flights leaving in the afternoon.

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

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

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 341 per week as of August 2025. The most frequent departure day is Mon, with 26% of weekly flights leaving on this day.

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 45% 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.

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 August 2025.

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.

$71 Cheap Flights from District of Columbia to Chicago in 2025

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

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

Find the cheapest flights from District of Columbia to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:10 am - 3:50 pmIAD-ORD

10h 40m1 stop

5:10 am - 12:55 pmORD-IAD

6h 45m1 stop

$142Frontier

Find Deal

Mon, Sep 29 - Mon, Oct 6

6:10 am - 3:58 pmIAD-MDW

10h 48m1 stop

6:20 am - 12:55 pmMDW-IAD

5h 35m1 stop

$142Frontier

Find Deal

Thu, Sep 4 - Mon, Sep 8

7:14 pm - 9:51 amIAD-MDW

15h 37m1 stop

12:06 pm - 8:46 pmMDW-IAD

7h 40m1 stop

$180

Find Deal

Fri, Oct 3 - Fri, Oct 10

9:05 am - 10:15 amDCA-MDW

2h 10mnonstop

10:15 am - 1:00 pmMDW-DCA

1h 45mnonstop

$189Southwest

Find Deal

Wed, Oct 8 - Wed, Oct 15

6:55 pm - 7:55 pmDCA-MDW

2h 00mnonstop

5:30 am - 8:20 amMDW-DCA

1h 50mnonstop

$197Southwest

Find Deal

Mon, Sep 15 - Mon, Sep 22

1:00 pm - 2:13 pmDCA-ORD

2h 13mnonstop

6:00 pm - 9:03 pmORD-DCA

2h 03mnonstop

$197United Airlines

Find Deal

Thu, Sep 11 - Sat, Sep 13

1:15 pm - 2:29 pmIAD-ORD

2h 14mnonstop

10:43 am - 1:49 pmORD-IAD

2h 06mnonstop

$197United Airlines

Find Deal

Thu, Sep 11 - Sat, Sep 13

9:00 am - 1:38 pmIAD-MDW

5h 38m1 stop

12:06 pm - 8:46 pmMDW-IAD

7h 40m1 stop

$197

Find Deal

Wed, Oct 8 - Fri, Oct 10

10:49 am - 12:02 pmDCA-ORD

2h 13mnonstop

6:54 pm - 10:00 pmORD-DCA

2h 06mnonstop

$198American Airlines

Find Deal

Wed, Sep 17 - Mon, Sep 22

6:00 pm - 7:26 pmDCA-ORD

2h 26mnonstop

6:06 am - 9:00 amORD-DCA

1h 54mnonstop

$237American Airlines

Find Deal

Sat, Aug 30 - Sun, Aug 31

Frontier flights from District of Columbia to Chicago

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

Frontier

Sep 29

IAD6:10 amWashington, D.C. Dulles Intl

10h 40m

1 stop

ORD3:50 pmChicago O'Hare Intl

Oct 6

ORD5:10 amChicago O'Hare Intl

6h 45m

1 stop

IAD12:55 pmWashington, D.C. Dulles Intl

$142

Find similar

Frontier

Sep 5

IAD1:55 pmWashington, D.C. Dulles Intl

11h 15m

1 stop

ORD12:10 amChicago O'Hare Intl

Sep 8

ORD5:10 amChicago O'Hare Intl

6h 45m

1 stop

IAD12:55 pmWashington, D.C. Dulles Intl

$143

Find similar

Frontier

Oct 15

IAD9:00 amWashington, D.C. Dulles Intl

5h 47m

1 stop

ORD1:47 pmChicago O'Hare Intl

Oct 16

ORD5:05 amChicago O'Hare Intl

9h 34m

1 stop

IAD3:39 pmWashington, D.C. Dulles Intl

$144

Find similar

United Airlines flights from District of Columbia to Chicago

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

United Airlines

Sep 11

DCA1:00 pmWashington, D.C. Reagan-National

2h 13m

ORD2:13 pmChicago O'Hare Intl

Sep 13

ORD6:00 pmChicago O'Hare Intl

2h 03m

DCA9:03 pmWashington, D.C. Reagan-National

$197

Find similar

United Airlines

Sep 11

DCA3:30 pmWashington, D.C. Reagan-National

2h 13m

ORD4:43 pmChicago O'Hare Intl

Sep 13

ORD11:46 amChicago O'Hare Intl

4h 56m

1 stop

DCA5:42 pmWashington, D.C. Reagan-National

$207

Find similar

United Airlines

Sep 13

DCA2:00 pmWashington, D.C. Reagan-National

2h 13m

ORD3:13 pmChicago O'Hare Intl

Sep 20

ORD1:12 pmChicago O'Hare Intl

6h 24m

1 stop

DCA8:36 pmWashington, D.C. Reagan-National

$227

Find similar

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

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 9/29

6:10 am-3:50 pm

1 stop10h 40m

Chicago O'Hare Intl

Mon 10/6

5:10 am-12:55 pm

1 stop6h 45m

$142

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 9/4

6:10 am-3:58 pm

1 stop10h 48m

Chicago Midway

Mon 9/8

6:20 am-12:55 pm

1 stop5h 35m

$142

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 10/3

7:14 pm-9:51 am

1 stop15h 37m

Chicago Midway

Fri 10/10

12:06 pm-8:46 pm

1 stop7h 40m

$180

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 10/8

9:05 am-10:15 am

Nonstop2h 10m

Chicago Midway

Wed 10/15

10:15 am-1:00 pm

Nonstop1h 45m

$189

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 9/15

6:55 pm-7:55 pm

Nonstop2h 00m

Chicago Midway

Mon 9/22

5:30 am-8:20 am

Nonstop1h 50m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 9/11

1:00 pm-2:13 pm

Nonstop2h 13m

Chicago O'Hare Intl

Sat 9/13

6:00 pm-9:03 pm

Nonstop2h 03m

$197

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 9/11

1:15 pm-2:29 pm

Nonstop2h 14m

Chicago O'Hare Intl

Sat 9/13

10:43 am-1:49 pm

Nonstop2h 06m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 10/8

9:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Fri 10/10

12:06 pm-8:46 pm

1 stop7h 40m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 9/17

10:49 am-12:02 pm

Nonstop2h 13m

Chicago O'Hare Intl

Mon 9/22

6:54 pm-10:00 pm

Nonstop2h 06m

$198

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 8/30

6:00 pm-7:26 pm

Nonstop2h 26m

Chicago O'Hare Intl

Sun 8/31

6:06 am-9:00 am

Nonstop1h 54m

$237

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 January is your next best option. Flight prices from District of Columbia to Chicago during January average around $229.

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 $495.

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 $333. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $437.

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 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 $324 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 $270 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	$71
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from District of Columbia in the past 72 hours is $71. The best round-trip flight deal from District of Columbia to Chicago found on momondo in the last 72 hours is $142.

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 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

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 August 2025.
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 737-800, making up 13.56% of the total bookings. Other popular models include Airbus A319 with 11.84%, Airbus A320-100/200 with 11.61%, and Boeing 737 MAX 8 with 8.20%.

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 $46	Free Cancellation	Rating 6.3 8,038 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $62	Free Cancellation	Rating 5.8 3,212 reviews	Search Frontier flights
Delta	PriceFrom $98	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
United Airlines	PriceFrom $157	Free Cancellation	Rating 7.4 8,925 reviews	Search United Airlines flights
American Airlines	PriceFrom $157	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $157	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

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.

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

Sat 8/23

Sat 8/30

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

Cheap flights from District of Columbia to Chicago from $71

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 9/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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

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

Frontier flights from District of Columbia to Chicago

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

United Airlines flights from District of Columbia to Chicago

Our best United 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

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

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?

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 $333. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $437.

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 to Chicago?

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.

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

Frontier, JetBlue, and Avelo Airlines are the most popular carriers operating 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?

The number of flights available between District of Columbia and Chicago is 48 per day as of August 2025. The most frequent departure time is 6:00AM, with 43% of daily flights leaving in the afternoon.

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 341 per week as of August 2025. The most frequent departure day is Mon, with 26% of weekly flights leaving on this day.

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

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

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

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

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

What is the most popular plane model 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?

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

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

How can momondo help me find flights 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?

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