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$96+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
1 adult, Economy
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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 Friday 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 July 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/117:48 am
IAD
-
ORD
1 stop13h 05m
Frontier
Wed 8/121:50 pm
ORD
-
IAD
1 stop8h 02m
Frontier
Deal found 7/22$219
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/108:33 pm
IAD
-
ORD
1 stop12h 29m
Frontier
Thu 8/131:50 pm
ORD
-
IAD
1 stop8h 02m
Frontier
Deal found 7/22$220
This Frontier deal was found by Cheapflights users on 7/22. 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.
Wed 9/97:00 am
IAD
-
MDW
1 stop4h 58m
Frontier
Mon 9/1412:03 pm
MDW
-
IAD
1 stop11h 25m
Frontier
Deal found 7/22$220
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Sun 9/65:15 pm
IAD
-
ORD
Nonstop2h 22m
United Airlines
Fri 9/116:25 am
ORD
-
IAD
Nonstop1h 58m
United Airlines
Deal found 7/22$223
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/118:33 pm
IAD
-
ORD
1 stop12h 29m
Frontier
Thu 8/131:50 pm
ORD
-
IAD
1 stop8h 02m
Frontier
Deal found 7/22$224
This Frontier deal was found by Cheapflights users on 7/22. 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.
Thu 10/87:00 am
IAD
-
MDW
1 stop4h 58m
Frontier
Tue 10/1312:03 pm
MDW
-
IAD
1 stop11h 25m
Frontier
Deal found 7/22$224
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/108:33 pm
IAD
-
ORD
1 stop12h 29m
Frontier
Mon 8/177:05 am
ORD
-
IAD
1 stop9h 09m
Frontier
Deal found 7/22$225
This Frontier deal was found by Cheapflights users on 7/22. 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.
Sun 8/236:20 am
IAD
-
MDW
1 stop5h 35m
Frontier
Sat 8/2911:45 am
MDW
-
IAD
1 stop10h 07m
Frontier
Deal found 7/22$225
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Thu 9/107:00 am
IAD
-
ORD
1 stop6h 02m
Frontier
Tue 9/156:30 am
ORD
-
IAD
1 stop10h 06m
Frontier
Deal found 7/22$226
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 9/227:00 am
IAD
-
ORD
1 stop13h 44m
Frontier
Thu 9/242:03 pm
ORD
-
IAD
1 stop9h 25m
Frontier
Deal found 7/21$227
This Priceline deal was found by Cheapflights users on 7/22. 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.
Thu 8/274:52 pm
IAD
-
ORD
1 stop7h 16m
Frontier
Sat 8/298:05 am
ORD
-
IAD
1 stop10h 39m
Frontier
Deal found 7/22$229
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Thu 9/36:20 am
IAD
-
ORD
1 stop14h 39m
Frontier
Tue 9/88:05 am
ORD
-
IAD
1 stop10h 39m
Frontier
Deal found 7/22$230

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 July 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$219
(Kiwi.com)

One-way from

$96
(Kiwi.com)

Popular in

January

Cheapest in

October

Average price

$372

Good round-trip deal

$378 or less

Good one-way deal

$231 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. 3% potential increase in price ($10 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 July 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 July 23, 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

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/5

12:30 pm-4:59 pm

1 stop5h 29m

Chicago Midway

Tue 9/8

9:29 am-4:30 pm

1 stop6h 01m

$231

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 9/24

6:10 am-7:25 am

Nonstop2h 15m

Chicago O'Hare Intl

Mon 9/28

8:50 am-11:55 am

Nonstop2h 05m

$257

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 8/15

12:30 pm-4:17 pm

1 stop4h 47m

Chicago O'Hare Intl

Tue 8/18

6:25 pm-12:34 am

1 stop5h 09m

$265

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 8/11

12:30 pm-4:15 pm

1 stop4h 45m

Chicago Midway

Tue 8/18

6:05 am-11:33 am

1 stop4h 28m

$265

Washington, D.C.Chicago

IAD - MDW

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

$288

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 9/3

12:40 pm-3:14 pm

1 stop3h 34m

Chicago O'Hare Intl

Sat 9/5

12:56 pm-4:02 pm

Nonstop2h 06m

$293

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 8/23

6:00 am-10:13 am

1 stop5h 13m

Chicago O'Hare Intl

Wed 8/26

5:30 am-11:33 am

1 stop5h 03m

$298

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 8/23

6:00 am-9:59 am

1 stop4h 59m

Chicago Midway

Wed 8/26

10:54 am-4:42 pm

1 stop4h 48m

$298

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 8/14

12:40 pm-3:14 pm

1 stop3h 34m

Chicago O'Hare Intl

Mon 8/17

9:39 pm-12:44 am

Nonstop2h 05m

$320
Quickest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 8/21

1:10 pm-2:27 pm

Nonstop2h 17m

Chicago O'Hare Intl

Mon 8/24

6:25 am-9:23 am

Nonstop1h 58m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 47 resultsSorted by cheapest first
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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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice 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 $283). 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 July 23, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 14% on flights from Washington, D.C. Dulles Intl Airport to Chicago by exploring options for tickets in the evening.

Weekly flight availability from Washington, D.C. Dulles Intl Airport to Chicago

Explore weekly flight availability from Dulles Intl to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 23, 2026.

The most flights from IAD to CHI are scheduled on a Tuesday (34 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

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

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 July 18, 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 July 23, 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
10,024 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

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
10,024 reviews
United Airlines
7.4
Good
10,024 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

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
2,770 reviews
United Airlines
7.4
Good
10,024 reviews

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

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?

    Delta and United Airlines can get you from Washington, D.C. Dulles Intl Airport to Chicago in just under 2h 15m. Your travel time can differ by up to 3h 14m. 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 $90. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $149 and $227, respectively. These flights start at 72% 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 (92%), Air China (83%), ANA( 77%).

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

    On average you can expect to pay $896 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $142 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 $283). 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
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Porter

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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 July 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$207FlexibilityNo cancel feeOn-time62%
DeltaCheapest$149Average$342FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$227Average$403FlexibilityNo cancel feeOn-time69%

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