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.

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

Delta and United Airlines 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 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: 86% of momondo users choosing 1-stop flights on this route connected there.

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 92% 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 connection time from Washington, D.C. Dulles Intl Airport to Chicago?

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

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

As of July 2026, there are 30 flights per day flying from Washington, D.C. Dulles Intl Airport to Chicago. The most common time of day flights depart is 8:00AM, with 45% of flights taking off at noon.

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 July 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.

$94 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 214 per week as of July 2026. The most frequent departure day is Fri, with 17% of weekly flights leaving on this day.

Discover deals from 900+ travel sites with momondo.

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.

6:20 am - 7:59 pm

IAD

ORD

14h 39m

1 stop

8:05 am - 7:44 pm

ORD

IAD

10h 39m

1 stop

$215Frontier

Mon, Aug 24 - Wed, Aug 26

6:20 am - 10:55 am

IAD

MDW

5h 35m

1 stop

6:05 am - 5:14 pm

MDW

IAD

10h 09m

1 stop

$215Frontier

Tue, Aug 18 - Wed, Aug 19

10:18 pm - 11:31 pm

IAD

ORD

2h 13mnonstop

9:52 pm - 12:58 am

ORD

IAD

2h 06mnonstop

$216United Airlines

Sat, Oct 10 - Mon, Oct 12

7:48 am - 7:53 pm

IAD

ORD

13h 05m

1 stop

1:50 pm - 10:52 pm

ORD

IAD

8h 02m

1 stop

$219Frontier

Tue, Aug 11 - Wed, Aug 12

8:33 pm - 8:02 am

IAD

ORD

12h 29m

1 stop

1:59 pm - 10:52 pm

ORD

IAD

7h 53m

1 stop

$220Frontier

Wed, Aug 12 - Tue, Aug 25

7:00 am - 10:58 am

IAD

MDW

4h 58m

1 stop

7:25 am - 5:36 pm

MDW

IAD

9h 11m

1 stop

$220Frontier

Sat, Sep 12 - Fri, Sep 18

7:00 am - 10:58 am

IAD

MDW

4h 58m

1 stop

7:25 am - 5:36 pm

MDW

IAD

9h 11m

1 stop

$221Frontier

Tue, Sep 22 - Thu, Sep 24

8:33 pm - 7:53 am

IAD

ORD

12h 20m

1 stop

1:59 pm - 10:52 pm

ORD

IAD

7h 53m

1 stop

$222Frontier

Mon, Aug 17 - Sat, Aug 22

7:50 am - 6:23 pm

IAD

ORD

11h 33m

1 stop

10:26 am - 12:10 am

ORD

IAD

12h 44m

1 stop

$223Frontier

Tue, Sep 22 - Thu, Sep 24

8:33 pm - 8:02 am

IAD

ORD

12h 29m

1 stop

1:50 pm - 10:52 pm

ORD

IAD

8h 02m

1 stop

$224Frontier

Tue, Aug 11 - Thu, Aug 13

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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

Aug 24

IAD6:20 amWashington, D.C. Dulles Intl

14h 39m

1 stop

ORD7:59 pmChicago O'Hare Intl

Aug 26

ORD8:05 amChicago O'Hare Intl

10h 39m

1 stop

IAD7:44 pmWashington, D.C. Dulles Intl

$215

Frontier

Aug 11

IAD7:48 amWashington, D.C. Dulles Intl

13h 05m

1 stop

ORD7:53 pmChicago O'Hare Intl

Aug 12

ORD1:50 pmChicago O'Hare Intl

8h 02m

1 stop

IAD10:52 pmWashington, D.C. Dulles Intl

$219

Frontier

Aug 12

IAD8:33 pmWashington, D.C. Dulles Intl

12h 29m

1 stop

ORD8:02 amChicago O'Hare Intl

Aug 18

ORD1:59 pmChicago O'Hare Intl

7h 53m

1 stop

IAD10:52 pmWashington, D.C. Dulles Intl

$220

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

Oct 10

IAD10:18 pmWashington, D.C. Dulles Intl

2h 13m

ORD11:31 pmChicago O'Hare Intl

Oct 12

ORD9:52 pmChicago O'Hare Intl

2h 06m

IAD12:58 amWashington, D.C. Dulles Intl

$216

United Airlines

Sep 2

IAD10:27 pmWashington, D.C. Dulles Intl

2h 13m

ORD11:40 pmChicago O'Hare Intl

Sep 6

ORD12:55 pmChicago O'Hare Intl

2h 06m

IAD4:01 pmWashington, D.C. Dulles Intl

$232

United Airlines

Aug 14

IAD6:15 amWashington, D.C. Dulles Intl

2h 15m

ORD7:30 amChicago O'Hare Intl

Aug 18

ORD10:50 amChicago O'Hare Intl

2h 05m

IAD1:55 pmWashington, D.C. Dulles Intl

$245

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

Mon 8/24

6:20 am-7:59 pm

1 stop14h 39m

Chicago O'Hare Intl

Wed 8/26

8:05 am-7:44 pm

1 stop10h 39m

$215

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 8/18

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Wed 8/19

6:05 am-5:14 pm

1 stop10h 09m

$215

Quickest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 10/10

10:18 pm-11:31 pm

Nonstop2h 13m

Chicago O'Hare Intl

Mon 10/12

9:52 pm-12:58 am

Nonstop2h 06m

$216

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 8/11

7:48 am-7:53 pm

1 stop13h 05m

Chicago O'Hare Intl

Wed 8/12

1:50 pm-10:52 pm

1 stop8h 02m

$219

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 8/12

8:33 pm-8:02 am

1 stop12h 29m

Chicago O'Hare Intl

Tue 8/25

1:59 pm-10:52 pm

1 stop7h 53m

$220

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/12

7:00 am-10:58 am

1 stop4h 58m

Chicago Midway

Fri 9/18

7:25 am-5:36 pm

1 stop9h 11m

$220

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 9/22

7:00 am-10:58 am

1 stop4h 58m

Chicago Midway

Thu 9/24

7:25 am-5:36 pm

1 stop9h 11m

$221

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 8/17

8:33 pm-7:53 am

1 stop12h 20m

Chicago O'Hare Intl

Sat 8/22

1:59 pm-10:52 pm

1 stop7h 53m

$222

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 9/22

7:50 am-6:23 pm

1 stop11h 33m

Chicago O'Hare Intl

Thu 9/24

10:26 am-12:10 am

1 stop12h 44m

$223

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 8/11

8:33 pm-8:02 am

1 stop12h 29m

Chicago O'Hare Intl

Thu 8/13

1:50 pm-10:52 pm

1 stop8h 02m

$224

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?

Prices are currently low for flights on this route.

Typical prices usually range from $265 to $443.
The lowest price recently found on this route was $215.

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Washington, D.C. Dulles Intl Airport, with most prices found around $283. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Washington, D.C. Dulles Intl Airport to Chicago during October average around $304.

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 $401. 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 $534.

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 $409. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $451.

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 $396 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 $230 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 18% 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 July 2026, prices for Washington, D.C. Dulles Intl Airport to Chicago flights are approximately 14% 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	$233
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 $233. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago found on momondo in the last 72 hours is $371.

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 July 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 15.39% of the total bookings. Other popular models include Airbus A321neo with 13.60%, Boeing 737 MAX 9 with 10.84%, and Boeing 737-800 with 10.12%.
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 (88% of total bookings). The next most popular airline is Frontier (12%).

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 2,769 reviews	Search Frontier flights
Delta	PriceFrom $149	Free Cancellation	Rating 7.8 8,486 reviews	Search Delta flights
United Airlines	PriceFrom $227	Free Cancellation	Rating 7.4 10,036 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 44 times per week, with 10,037 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 $227 (round-trip), much lower than the average airfare cost of $403 for United Airlines flights on this route.

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 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 $94

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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

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

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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 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

Best Price Found

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

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.

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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

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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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