HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$91+ Cheap flights from Dulles Intl (IAD) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Sep 10 — Sep 171
Thu 9/10
Thu 9/17
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Dulles Intl to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Washington, D.C. Dulles Intl to Chicago are usually found in October or September, booked 45 days in advance, depart on a Thursday or Wednesday and return on a Friday

Cheap flight deals from Dulles Intl to Chicago

Cheapest flights from Dulles Intl to Chicago
Explore the most affordable flight options available from Dulles Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 11, 2026.

This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:15 am -
Nonstop2h 15m
Sat 9/56:30 am -
Nonstop1h 58m
Deal found 8/10$186
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:09 pm -
1 stop19h 41m
Thu 9/107:28 pm -
1 stop20h 50m
Deal found 8/9$187
This Kissandfly.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:27 pm -
Nonstop2h 13m
Mon 9/1410:26 am -
1 stop5h 52m
Deal found 8/8$188
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
1 stop6h 02m
Fri 11/132:03 pm -
1 stop9h 25m
Deal found 8/10$189
This CheapOair deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:20 am -
1 stop5h 35m
Sat 9/56:05 am -
1 stop10h 09m
Deal found 8/7$189
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/79:44 pm -
2 stops23h 24m
Mon 9/147:11 am -
1 stop11h 58m
Deal found 8/10$190
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:15 pm -
Nonstop2h 14m
Wed 9/1612:55 pm -
Nonstop2h 06m
Deal found 8/10$191
This Trip.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:20 am -
1 stop5h 35m
Tue 9/111:50 am -
1 stop10h 02m
Deal found 8/6$191
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:00 am -
1 stop14h 08m
Sun 9/67:05 am -
1 stop9h 09m
Deal found 8/10$192
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:05 am -
1 stop13h 03m
Sat 9/126:20 am -
1 stop9h 58m
Deal found 8/7$193
This Priceline deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
1 stop4h 58m
Thu 11/127:25 am -
1 stop9h 11m
Deal found 8/7$193
This CheapOair deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:50 am -
1 stop10h 56m
Tue 9/226:25 am -
1 stop9h 53m
Deal found 8/7$194

Find flight deals from Dulles Intl to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Dulles Intl (IAD) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$186
(United Airlines)

One-way from

$91
(Trip.com)

Popular in

January

Cheapest in

October

Average price

$358

Good round-trip deal

$353 or less

Good one-way deal

$241 or less
Provider with most accurate pricing for Washington, D.C. Dulles Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. Dulles Intl-Chicago (CHI) flights.
Search Deals
From Washington, D.C. Dulles Intl to Chicago (CHI)
Search Deals
One-way flight from Washington, D.C. Dulles Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Washington, D.C. Dulles Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Washington, D.C. Dulles Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Dulles Intl to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 11, 2026.
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
Quickest round-trip

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Sat 9/5

10:27 pm-11:40 pm

Nonstop2h 13m

Chicago O'Hare Intl

Mon 9/7

6:25 am-9:23 am

Nonstop1h 58m

$208

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Fri 12/4

12:30 pm-4:14 pm

1 stop4h 44m

Chicago Midway

Tue 12/8

9:30 am-4:26 pm

1 stop5h 56m

$238

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Thu 9/17

6:13 am-7:28 am

Nonstop2h 15m

Chicago O'Hare Intl

Tue 9/22

9:39 pm-12:44 am

Nonstop2h 05m

$255

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Tue 10/27

6:11 am-7:29 am

Nonstop2h 18m

Chicago O'Hare Intl

Wed 10/28

6:04 am-8:58 am

Nonstop1h 54m

$255

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Sat 9/5

5:47 pm-10:36 pm

1 stop5h 49m

Chicago Midway

Tue 9/8

5:37 pm-11:14 pm

1 stop4h 37m

$258

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Thu 9/10

6:07 pm-11:59 pm

1 stop6h 52m

Chicago O'Hare Intl

Mon 9/14

5:10 pm-11:14 pm

1 stop5h 04m

$275

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Sat 9/19

6:10 am-9:07 am

1 stop3h 57m

Chicago Midway

Sat 9/19

6:40 pm-11:14 pm

1 stop3h 34m

$275

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Mon 9/28

6:00 am-9:49 am

1 stop4h 49m

Chicago Midway

Wed 9/30

1:00 pm-8:14 pm

1 stop6h 14m

$275

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Thu 10/1

6:10 am-9:07 am

1 stop3h 57m

Chicago Midway

Mon 10/5

5:10 pm-12:41 am

1 stop6h 31m

$275

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Tue 10/6

10:18 pm-11:32 pm

Nonstop2h 14m

Chicago O'Hare Intl

Fri 10/9

9:52 pm-12:58 am

Nonstop2h 06m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/7

Showing 1-10 of 41 resultsSorted by cheapest first
1
2
3
...
5

Compare providers for flights from Dulles Intl to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Dulles Intl to Chicago in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Washington, D.C. Dulles Intl Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C. Dulles Intl Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C. Dulles Intl Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Washington, D.C. Dulles Intl Airport-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C. Dulles Intl Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Dulles Intl to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Dulles Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Washington, D.C. Dulles Intl Airport to Chicago

What is the cheapest month to book a flight from Washington, D.C. Dulles Intl Airport to Chicago?

Currently, September is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $273). Flying from Washington, D.C. Dulles Intl Airport to Chicago in March is currently the most expensive (average of $456). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IAD to CHI?

Find hourly flight availability from Dulles Intl to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 11, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 16% on flights from Washington, D.C. Dulles Intl Airport to Chicago by exploring options for tickets in the evening.

How much does it cost to fly round-trip from Washington, D.C. Dulles Intl Airport to Chicago?

Airfare is below average for this route at the moment.
Washington, D.C. Dulles Intl Airport to Chicago flights typically cost between $257 and $449 in September.
The cheapest round-trip price found within the last 5 days was $184 on United Airlines (Sep 5-Sep 12).

How far ahead should I book a flight from Washington, D.C. Dulles Intl Airport to Chicago?

Booking 85 days in advance of your planned departure date is, on average, the best time to get cheap flights from Washington, D.C. Dulles Intl Airport to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest day to fly from Washington, D.C. Dulles Intl Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Dulles Intl to Chicago. Price data was last updated on August 8, 2026.

Travelers seeking maximum savings on their Washington, D.C. Dulles Intl Airport to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Washington, D.C. Dulles Intl Airport to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Dulles Intl Airport to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and IAD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 11, 2026.
See what other customers who have flown with United Airlines and Frontier from Washington, D.C. Dulles Intl Airport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,102 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
United Airlines
7.4
Good
10,102 reviews
United Airlines
7.4
Good
10,102 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
Frontier
5.6
Fair
2,706 reviews
United Airlines
7.4
Good
10,102 reviews

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Food

6.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

Related info for your journey

Find useful and relevant information for your journey from Dulles Intl to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Washington, D.C. Dulles Intl Airport to Chicago?

    United Airlines and Delta can get you from Washington, D.C. Dulles Intl Airport to Chicago in just under 2h 13m. Your travel time can differ by up to 2h 31m. The distance from Washington, D.C. Dulles Intl Airport to Chicago is about 587 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Washington, D.C. Dulles Intl Airport to Chicago round-trip?

    Flying on Frontier is currently your cheapest option to Chicago, with prices starting at $70. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $149 and $215, respectively. These flights start at 79% lower than the current average price 3 months from now.

  • What are the most reliable airlines from Washington, D.C. Dulles Intl Airport to Chicago?

    Before booking your flight to Chicago from Washington, D.C. Dulles Intl Airport, check out the most reliable airlines to get you to your destination on time: Egyptair (93%), ANA (77%), Ethiopian Air( 75%).

  • What are the cheapest flights from Washington, D.C. Dulles Intl Airport to Chicago?

    On average you can expect to pay $830 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $155 while the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) is currently priced at $177.

  • Can I find deals for flights from Dulles Intl to Chicago that include hotel bookings?

    Yes. In addition to deals on Dulles Intl to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Dulles Intl to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Dulles Intl to Chicago.

  • Can I find deals for business class flights from Dulles Intl to Chicago?

    Yes. Cheapflights offers flight deals from Dulles Intl to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Washington, D.C. Dulles Intl Airport to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $273). Flying from Washington, D.C. Dulles Intl Airport to Chicago in March is currently the most expensive (average of $456). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 3 airlines flying from Dulles Intl to Chicago

Discover the top 3 airlines that operate flights from Dulles Intl to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$70Average$207FlexibilityNo cancel feeOn-time62%
DeltaCheapest$149Average$408FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$400FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.