Which layover airport offers the lowest fares from Washington, D.C. Dulles Intl Airport to Chicago?

Flights via Atlanta (ATL) offer the lowest average round-trip price of $182.

Which layover airport has the shortest connection time from Washington, D.C. Dulles Intl Airport to Chicago?

Detroit (DTW) has the shortest average layover time for this route: 0h 53m.

What is the cheapest airline that flies from Washington, D.C. Dulles Intl to Chicago?

United Airlines and Delta are the most popular carriers operating from Washington, D.C. Dulles Intl to Chicago

Which layover airport has the shortest travel time from Washington, D.C. Dulles Intl Airport to Chicago?

Flights connecting via Detroit (DTW) have the shortest average one-way travel time: 3h 40m.

What airlines fly to Chicago?

United Airlines, Frontier and Delta are the top three most popular airlines that fly to Chicago from Washington, D.C. Dulles Intl Airport according to our data. United Airlines is the first choice among our users, with 87% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Which airport is the most popular layover for flights between Washington, D.C. Dulles Intl Airport and Chicago?

Atlanta (ATL) was the most common stop: 86% of momondo users choosing 1-stop flights on this route connected there.

How many flights depart from Washington, D.C. Dulles Intl Airport to Chicago on average per day?

As of March 2026, there are 4 flights per day flying from Washington, D.C. Dulles Intl Airport to Chicago. The most common time of day flights depart is 5:00PM, with 49% of flights taking off in the afternoon.

How many operators does momondo search for flights from Washington, D.C. Dulles Intl Airport to Chicago?

The number of operators available for flights from Washington, D.C. Dulles Intl Airport to Chicago is 3 as of March 2026.

How old do you have to be to fly from Washington, D.C. Dulles Intl Airport to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Washington, D.C. Dulles Intl Airport 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.

$74 Cheap Flights from Washington, D.C. Dulles Intl Airport to Chicago in 2026

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Find the cheapest flights from Washington, D.C. Dulles Intl Airport to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 11:37 am

IAD

ORD

6h 37m

1 stop

4:57 pm - 7:27 am

ORD

IAD

13h 30m

1 stop

$187Frontier

Fri, Apr 17 - Sun, Apr 19

6:00 am - 11:32 am

IAD

ORD

6h 32m

1 stop

6:00 am - 7:32 am

ORD

IAD

24h 32m

1 stop

$188Frontier

Fri, Apr 24 - Sun, Apr 26

2:39 pm - 11:44 pm

IAD

ORD

10h 05m

1 stop

4:51 pm - 12:21 am

ORD

IAD

6h 30m

1 stop

$189Frontier

Mon, Mar 23 - Wed, Mar 25

10:51 am - 7:59 am

IAD

MDW

22h 08m

2 stops

2:15 pm - 12:36 am

MDW

IAD

9h 21m

1 stop

$189Frontier

Sat, Apr 18 - Tue, Apr 21

5:05 am - 10:01 pm

IAD

ORD

17h 56m

1 stop

7:41 pm - 12:21 am

ORD

IAD

27h 40m

1 stop

$190Frontier

Sat, Mar 14 - Tue, Mar 17

6:39 pm - 5:00 pm

IAD

ORD

47h 21m

2 stops

4:28 pm - 12:36 am

ORD

IAD

7h 08m

1 stop

$191Frontier

Sun, Apr 12 - Sat, Apr 18

6:15 am - 10:19 pm

IAD

MDW

17h 04m

1 stop

6:00 am - 5:34 pm

MDW

IAD

10h 34m

1 stop

$191Frontier

Mon, Apr 13 - Mon, Apr 20

6:00 am - 11:37 am

IAD

ORD

6h 37m

1 stop

2:09 pm - 12:36 am

ORD

IAD

9h 27m

2 stops

$192Multiple Airlines

Fri, Apr 17 - Tue, Apr 21

1:31 pm - 4:00 pm

IAD

MDW

27h 29m

1 stop

9:04 am - 7:27 am

MDW

IAD

21h 23m

1 stop

$192Frontier

Fri, Apr 17 - Sun, Apr 19

10:25 pm - 1:00 pm

IAD

MDW

15h 35m

2 stops

6:00 am - 5:34 pm

MDW

IAD

10h 34m

1 stop

$194Multiple Airlines

Mon, Apr 13 - Mon, Apr 20

Frontier flights from Washington, D.C. Dulles Intl Airport to Chicago

Our best Frontier deals on Washington, D.C. Dulles Intl Airport to Chicago flight tickets

Frontier

Apr 17

IAD6:00 amWashington, D.C. Dulles Intl

6h 37m

1 stop

ORD11:37 amChicago O'Hare Intl

Apr 19

ORD4:57 pmChicago O'Hare Intl

13h 30m

1 stop

IAD7:27 amWashington, D.C. Dulles Intl

$187

Frontier

Mar 11

IAD6:20 amWashington, D.C. Dulles Intl

12h 37m

1 stop

ORD5:57 pmChicago O'Hare Intl

Mar 12

ORD4:28 pmChicago O'Hare Intl

7h 03m

1 stop

IAD12:31 amWashington, D.C. Dulles Intl

$188

Frontier

Mar 23

IAD2:39 pmWashington, D.C. Dulles Intl

10h 05m

1 stop

ORD11:44 pmChicago O'Hare Intl

Mar 25

ORD4:51 pmChicago O'Hare Intl

6h 30m

1 stop

IAD12:21 amWashington, D.C. Dulles Intl

$189

United Airlines flights from Washington, D.C. Dulles Intl Airport to Chicago

Our best United Airlines deals on Washington, D.C. Dulles Intl Airport to Chicago flight tickets

United Airlines

Apr 4

IAD8:20 amWashington, D.C. Dulles Intl

2h 18m

ORD9:38 amChicago O'Hare Intl

Apr 4

ORD9:35 pmChicago O'Hare Intl

1h 57m

IAD12:32 amWashington, D.C. Dulles Intl

$206

United Airlines

Apr 8

IAD10:30 pmWashington, D.C. Dulles Intl

2h 13m

ORD11:43 pmChicago O'Hare Intl

Apr 11

ORD2:25 pmChicago O'Hare Intl

2h 03m

IAD5:28 pmWashington, D.C. Dulles Intl

$211

United Airlines

Mar 24

IAD8:32 amWashington, D.C. Dulles Intl

2h 18m

ORD9:50 amChicago O'Hare Intl

Mar 31

ORD8:45 amChicago O'Hare Intl

2h 03m

IAD11:48 amWashington, D.C. Dulles Intl

$229

momondo Fare Finder

Use the filters below to find and compare flights from Washington, D.C. Dulles Intl Airport 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

Fri 4/17

6:00 am-11:37 am

1 stop6h 37m

Chicago O'Hare Intl

Sun 4/19

4:57 pm-7:27 am

1 stop13h 30m

$187

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 4/24

6:00 am-11:32 am

1 stop6h 32m

Chicago O'Hare Intl

Sun 4/26

6:00 am-7:32 am

1 stop24h 32m

$188

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 3/23

2:39 pm-11:44 pm

1 stop10h 05m

Chicago O'Hare Intl

Wed 3/25

4:51 pm-12:21 am

1 stop6h 30m

$189

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 4/18

10:51 am-7:59 am

2 stops22h 08m

Chicago Midway

Tue 4/21

2:15 pm-12:36 am

1 stop9h 21m

$189

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 3/14

5:05 am-10:01 pm

1 stop17h 56m

Chicago O'Hare Intl

Tue 3/17

7:41 pm-12:21 am

1 stop27h 40m

$190

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 4/12

6:39 pm-5:00 pm

2 stops47h 21m

Chicago O'Hare Intl

Sat 4/18

4:28 pm-12:36 am

1 stop7h 08m

$191

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/13

6:15 am-10:19 pm

1 stop17h 04m

Chicago Midway

Mon 4/20

6:00 am-5:34 pm

1 stop10h 34m

$191

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 4/17

6:00 am-11:37 am

1 stop6h 37m

Chicago O'Hare Intl

Tue 4/21

2:09 pm-12:36 am

2 stops9h 27m

$192

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 4/17

1:31 pm-4:00 pm

1 stop27h 29m

Chicago Midway

Sun 4/19

9:04 am-7:27 am

1 stop21h 23m

$192

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 4/13

10:25 pm-1:00 pm

2 stops15h 35m

Chicago Midway

Mon 4/20

6:00 am-5:34 pm

1 stop10h 34m

$194

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 Washington, D.C. Dulles Intl Airport 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

Layovers

Other information

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Washington, D.C. Dulles Intl Airport, with most prices found around $261. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Washington, D.C. Dulles Intl Airport to Chicago during September average around $264.

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 $382. 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 Washington, D.C. Dulles Intl Airport to Chicago for around $505.

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 Washington, D.C. Dulles Intl Airport to Chicago during this time can be as low as $365. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $421.

What is the cheapest Washington, D.C. Dulles Intl to Chicago flight route?

Fly from Washington, D.C. Dulles Intl to Chicago O'Hare Intl for the best Washington, D.C. Dulles Intl - 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 Washington, D.C. Dulles Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $349 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Washington, D.C. Dulles Intl Airport for as low as $199 on momondo.

What cabin class options are available on Washington, D.C. Dulles Intl to Chicago flights?

There are 4 cabin classes available to choose from on Washington, D.C. Dulles Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Washington, D.C. Dulles Intl Airport to Chicago flight prices changed over time?

As of March 2026, prices for Washington, D.C. Dulles Intl Airport to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.

When to book flights from Washington, D.C. Dulles Intl Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. Dulles Intl Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Washington, D.C. Dulles Intl Airport to Chicago (IAD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. Dulles Intl Airport to Chicago

Best Price Found	$173
Fastest flight time	2h 11m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Washington, D.C. Dulles Intl Airport in the past 72 hours is $173. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago found on momondo in the last 72 hours is $336.

The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago takes 2h 11m

Direct flights go from Washington, D.C. Dulles Intl Airport to Chicago every day.

There are 3 airports in Chicago. From Washington, D.C. Dulles Intl Airport there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

How far is Washington, D.C. Dulles Intl to Chicago by plane?
The distance between Washington, D.C. Dulles Intl and Chicago is about 571.5 mi. Flights usually cover this in 2h 11m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Washington, D.C. Dulles Intl Airport to Chicago?
Prices for flights from Washington, D.C. Dulles Intl Airport to Chicago refresh daily.
How many operators does momondo search for flights from Washington, D.C. Dulles Intl Airport to Chicago?
The number of operators available for flights from Washington, D.C. Dulles Intl Airport to Chicago is 3 as of March 2026.
How old do you have to be to fly from Washington, D.C. Dulles Intl Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Washington, D.C. Dulles Intl Airport 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 Washington, D.C. Dulles Intl Airport to Chicago?
Based on momondo bookings for flights between Washington, D.C. Dulles Intl Airport and Chicago, the leading plane model is Boeing 737-900, making up 14.63% of the total bookings. Other popular models include Airbus A321neo with 10.42%, Boeing 737-800 with 10.15%, and Boeing 737 MAX 8 with 10.08%.
What is the most popular airline from Washington, D.C. Dulles Intl Airport to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Washington, D.C. Dulles Intl Airport to Chicago is United Airlines (81% of total bookings). The next most popular airlines are Frontier (17%) and Delta (2%).

Best airlines flying from Washington, D.C. Dulles Intl Airport to Chicago

Compare and see reviews for airlines that fly from Washington, D.C. Dulles Intl Airport to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $106	Free Cancellation	Rating 5.7 3,041 reviews	Search Frontier flights
Delta	PriceFrom $194	Free Cancellation	Rating 7.9 8,246 reviews	Search Delta flights
United Airlines	PriceFrom $202	Free Cancellation	Rating 7.4 9,381 reviews	Search United Airlines flights

United Airlines Flights From Washington, D.C. Dulles Intl Airport to Chicago
United Airlines flies from Washington, D.C. Dulles Intl Airport to Chicago around 8 times per week, with 9,381 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Washington, D.C. Dulles Intl Airport to Chicago in the last 72 hours was $202 (round-trip), much lower than the average airfare cost of $343 for United Airlines flights on this route.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Washington, D.C..

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Washington, D.C. which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Washington, D.C. to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Washington, D.C..

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Washington, D.C. are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $74

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Frontier flights from Washington, D.C. Dulles Intl Airport to Chicago

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Use the filters below to find and compare flights from Washington, D.C. Dulles Intl Airport to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Washington, D.C. Dulles Intl Airport 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 Washington, D.C. Dulles Intl to Chicago flight route?

How far in advance should I book a flight to Chicago?

What cabin class options are available on Washington, D.C. Dulles Intl to Chicago flights?

How have Washington, D.C. Dulles Intl Airport to Chicago flight prices changed over time?

What is the cheapest airline that flies from Washington, D.C. Dulles Intl to Chicago?

What airlines fly to Chicago?

Which airport is the most popular layover for flights between Washington, D.C. Dulles Intl Airport and Chicago?

Which layover airport offers the lowest fares from Washington, D.C. Dulles Intl Airport to Chicago?

Which layover airport has the shortest travel time from Washington, D.C. Dulles Intl Airport to Chicago?

Which layover airport has the shortest connection time from Washington, D.C. Dulles Intl Airport to Chicago?

How many flights depart from Washington, D.C. Dulles Intl Airport to Chicago on average per day?

How many flights depart from Washington, D.C. Dulles Intl Airport to Chicago on average per week?

When to book flights from Washington, D.C. Dulles Intl Airport to Chicago

Cheap Washington, D.C. Dulles Intl Airport to Chicago (IAD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. Dulles Intl Airport to Chicago

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Fastest flight time

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Airports in Chicago

Best airlines flying from Washington, D.C. Dulles Intl Airport to Chicago

Compare and see reviews for airlines that fly from Washington, D.C. Dulles Intl Airport to Chicago with momondo

United Airlines Flights From Washington, D.C. Dulles Intl Airport to Chicago

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Airports listed have a maximum distance of 78.5 mi from Chicago

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