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 $142.

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

As of June 2026, there are 29 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 47% of flights taking off in the afternoon.

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

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 5h 47m.

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: 78% of momondo users choosing 1-stop flights on this route connected there.

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

Atlanta (ATL) has the shortest average layover time for this route: 2h 40m.

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

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 June 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.

$99 Cheap Flights from Washington, D.C. Dulles Intl Airport to Chicago in 2026

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

The number of flights available between Washington, D.C. Dulles Intl Airport and Chicago is 209 per week as of June 2026. The most frequent departure day is Wed, with 17% of weekly flights leaving on this day.

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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.

11:17 am - 7:50 pm

IAD

ORD

9h 33m

1 stop

9:28 am - 9:12 pm

ORD

IAD

10h 44m

1 stop

$240Frontier

Wed, Jul 1 - Sat, Jul 11

11:17 am - 10:11 pm

IAD

MDW

11h 54m

1 stop

12:11 pm - 10:55 pm

MDW

IAD

9h 44m

1 stop

$240Frontier

Fri, Jul 3 - Tue, Jul 7

12:25 pm - 5:13 pm

IAD

ORD

5h 48m

1 stop

6:40 am - 2:18 pm

ORD

IAD

6h 38m

1 stop

$241Delta

Mon, Sep 28 - Wed, Sep 30

5:30 pm - 10:25 pm

IAD

MDW

5h 55m

1 stop

6:05 am - 11:36 am

MDW

IAD

4h 31m

1 stop

$241Delta

Mon, Sep 28 - Wed, Sep 30

8:57 pm - 8:03 am

IAD

ORD

12h 06m

1 stop

5:13 pm - 10:16 am

ORD

IAD

16h 03m

1 stop

$242Frontier

Thu, Jul 2 - Tue, Jul 7

8:15 am - 9:36 am

IAD

ORD

2h 21mnonstop

6:30 am - 9:24 am

ORD

IAD

1h 54mnonstop

$243United Airlines

Wed, Jun 24 - Wed, Jul 1

7:30 am - 10:11 pm

IAD

MDW

15h 41m

1 stop

6:00 am - 11:17 pm

MDW

IAD

16h 17m

1 stop

$243Frontier

Thu, Sep 3 - Mon, Sep 7

8:33 pm - 7:53 am

IAD

ORD

12h 20m

1 stop

7:05 am - 5:14 pm

ORD

IAD

9h 09m

1 stop

$244Frontier

Tue, Aug 11 - Mon, Aug 17

3:40 pm - 4:59 pm

IAD

ORD

2h 19mnonstop

6:25 am - 9:23 am

ORD

IAD

1h 58mnonstop

$245United Airlines

Thu, Aug 27 - Mon, Aug 31

12:00 pm - 11:10 pm

IAD

ORD

12h 10m

2 stops

1:50 pm - 10:55 pm

ORD

IAD

8h 05m

1 stop

$248Multiple Airlines

Fri, Jul 31 - Thu, Aug 6

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

Jul 1

IAD11:17 amWashington, D.C. Dulles Intl

9h 33m

1 stop

ORD7:50 pmChicago O'Hare Intl

Jul 11

ORD9:28 amChicago O'Hare Intl

10h 44m

1 stop

IAD9:12 pmWashington, D.C. Dulles Intl

$240

Frontier

Jul 2

IAD8:57 pmWashington, D.C. Dulles Intl

12h 06m

1 stop

ORD8:03 amChicago O'Hare Intl

Jul 7

ORD5:13 pmChicago O'Hare Intl

16h 03m

1 stop

IAD10:16 amWashington, D.C. Dulles Intl

$242

Frontier

Sep 3

IAD7:30 amWashington, D.C. Dulles Intl

15h 41m

1 stop

MDW10:11 pmChicago Midway

Sep 7

MDW6:00 amChicago Midway

16h 17m

1 stop

IAD11:17 pmWashington, D.C. Dulles Intl

$243

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

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

Delta

Sep 28

IAD12:25 pmWashington, D.C. Dulles Intl

5h 48m

1 stop

ORD5:13 pmChicago O'Hare Intl

Sep 30

ORD6:40 amChicago O'Hare Intl

6h 38m

1 stop

IAD2:18 pmWashington, D.C. Dulles Intl

$241

Delta

Jul 1

IAD6:00 amWashington, D.C. Dulles Intl

4h 14m

1 stop

MDW9:14 amChicago Midway

Jul 4

MDW5:50 pmChicago Midway

4h 24m

1 stop

IAD11:14 pmWashington, D.C. Dulles Intl

$259

Delta

Aug 27

IAD11:10 amWashington, D.C. Dulles Intl

6h 14m

1 stop

ORD4:24 pmChicago O'Hare Intl

Aug 31

ORD5:28 amChicago O'Hare Intl

5h 05m

1 stop

IAD11:33 amWashington, D.C. Dulles Intl

$265

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

Cheapest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 7/1

11:17 am-7:50 pm

1 stop9h 33m

Chicago O'Hare Intl

Sat 7/11

9:28 am-9:12 pm

1 stop10h 44m

$240

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 7/3

11:17 am-10:11 pm

1 stop11h 54m

Chicago Midway

Tue 7/7

12:11 pm-10:55 pm

1 stop9h 44m

$240

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 9/28

12:25 pm-5:13 pm

1 stop5h 48m

Chicago O'Hare Intl

Wed 9/30

6:40 am-2:18 pm

1 stop6h 38m

$241

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 9/28

5:30 pm-10:25 pm

1 stop5h 55m

Chicago Midway

Wed 9/30

6:05 am-11:36 am

1 stop4h 31m

$241

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 7/2

8:57 pm-8:03 am

1 stop12h 06m

Chicago O'Hare Intl

Tue 7/7

5:13 pm-10:16 am

1 stop16h 03m

$242

Quickest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 6/24

8:15 am-9:36 am

Nonstop2h 21m

Chicago O'Hare Intl

Wed 7/1

6:30 am-9:24 am

Nonstop1h 54m

$243

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 9/3

7:30 am-10:11 pm

1 stop15h 41m

Chicago Midway

Mon 9/7

6:00 am-11:17 pm

1 stop16h 17m

$243

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 8/11

8:33 pm-7:53 am

1 stop12h 20m

Chicago O'Hare Intl

Mon 8/17

7:05 am-5:14 pm

1 stop9h 09m

$244

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 8/27

3:40 pm-4:59 pm

Nonstop2h 19m

Chicago O'Hare Intl

Mon 8/31

6:25 am-9:23 am

Nonstop1h 58m

$245

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 7/31

12:00 pm-11:10 pm

2 stops12h 10m

Chicago O'Hare Intl

Thu 8/6

1:50 pm-10:55 pm

1 stop8h 05m

$248

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 typical price of a round-trip flight between Washington, D.C. Dulles Intl Airport and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Washington, D.C. Dulles Intl Airport, with most prices found around $38. If you’re not able to fly to Chicago in January, then April is your next best option. Flight prices from Washington, D.C. Dulles Intl Airport to Chicago during April average around $70.

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 $397. 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 Washington, D.C. Dulles Intl Airport to Chicago for around $526.

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 $397. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $440.

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 from Washington, D.C. Dulles Intl Airport 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 $379 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 $198 on momondo.

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

There are 4 cabin classes available to choose from on Washington, D.C. Dulles Intl Airport 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 Washington, D.C. Dulles Intl Airport to Chicago flights?

You could potentially save up to 17% on your flight if you consider stops on a Washington, D.C. Dulles Intl Airport to Chicago flight.

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

As of June 2026, prices for Washington, D.C. Dulles Intl Airport to Chicago flights are approximately 2% cheaper 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	$193
Fastest flight time	2h 03m
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 $193. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago found on momondo in the last 72 hours is $361.

The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago takes 2h 03m

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

Frequently asked questions about flying from Washington, D.C. Dulles Intl Airport to Chicago

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 03m, 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 June 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 14.51% of the total bookings. Other popular models include Airbus A321neo with 13.26%, Boeing 737 MAX 8 with 12.62%, and Boeing 737-800 with 10.87%.
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 (84% of total bookings). The next most popular airline is Frontier (16%).

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 $90	Free Cancellation	Rating 5.6 2,912 reviews	Search Frontier flights
Delta	PriceFrom $149	Free Cancellation	Rating 7.8 8,396 reviews	Search Delta flights
United Airlines	PriceFrom $222	Free Cancellation	Rating 7.4 9,779 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 38 times per week, with 9,780 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 $222 (round-trip), much lower than the average airfare cost of $382 for United Airlines flights on this route.

Merrillville

New Buffalo

Hammond

Saint Joseph

Portage

Benton Harbor

Lansing

Valparaiso

Schererville

Munster

Crown Point

Monticello

Chesterton

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 $99

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

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

What is the typical price of a round-trip flight between Washington, D.C. Dulles Intl Airport and 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 from Washington, D.C. Dulles Intl Airport to Chicago?

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

Can stopping save me money on Washington, D.C. Dulles Intl Airport 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

Direct flights

Airports in Chicago

Frequently asked questions about flying from Washington, D.C. Dulles Intl Airport to 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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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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