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$100+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
May 27 — Jun 31
Wed 5/27
Wed 6/3
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 84 days in advance, depart on a Friday or Thursday 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 April 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/1911:07 am
IAD
-
MDW
1 stop11h 55m
Multiple Airlines
Thu 5/219:14 am
MDW
-
IAD
1 stop7h 14m
Multiple Airlines
Deal found 4/22$219
This Trip.com deal was found by Cheapflights users on 4/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/811:12 am
IAD
-
MDW
1 stop11h 50m
Frontier
Tue 5/126:00 am
MDW
-
IAD
1 stop9h 21m
Frontier
Deal found 4/22$220
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
Wed 5/136:27 pm
IAD
-
ORD
2 stops21h 12m
Frontier
Thu 5/145:30 pm
ORD
-
IAD
1 stop24h 12m
Frontier
Deal found 4/24$221
This Expedia deal was found by Cheapflights users on 4/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:37 pm
IAD
-
ORD
1 stop29h 36m
Frontier
Thu 5/71:59 pm
ORD
-
IAD
1 stop8h 10m
Frontier
Deal found 4/27$222
This Expedia deal was found by Cheapflights users on 4/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/511:07 am
IAD
-
MDW
1 stop11h 55m
Frontier
Thu 5/712:19 pm
MDW
-
IAD
1 stop9h 50m
Frontier
Deal found 4/27$222
This United Airlines deal was found by Cheapflights users on 4/23. 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 5/146:15 am
IAD
-
ORD
Nonstop2h 11m
United Airlines
Thu 5/1412:55 pm
ORD
-
IAD
Nonstop2h 03m
United Airlines
Deal found 4/23$223
This Frontier deal was found by Cheapflights users on 4/26. 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 5/611:12 am
IAD
-
MDW
1 stop11h 50m
Frontier
Sat 5/96:00 am
MDW
-
IAD
1 stop9h 21m
Frontier
Deal found 4/26$223
This Frontier deal was found by Cheapflights users on 4/26. 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 7/18:57 pm
IAD
-
ORD
1 stop12h 06m
Frontier
Fri 7/109:28 am
ORD
-
IAD
1 stop8h 17m
Frontier
Deal found 4/26$224
This Frontier deal was found by Cheapflights users on 4/27. 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 7/111:17 am
IAD
-
MDW
1 stop11h 54m
Frontier
Tue 7/76:00 am
MDW
-
IAD
1 stop9h 11m
Frontier
Deal found 4/27$224
This Frontier deal was found by Cheapflights users on 4/22. 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 5/2411:07 am
IAD
-
ORD
1 stop9h 34m
Frontier
Thu 5/281:50 pm
ORD
-
IAD
1 stop8h 19m
Frontier
Deal found 4/22$225
This Expedia deal was found by Cheapflights users on 4/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:07 am
IAD
-
MDW
1 stop11h 55m
Frontier
Wed 5/276:00 am
MDW
-
IAD
1 stop10h 27m
Frontier
Deal found 4/23$225
This Priceline deal was found by Cheapflights users on 4/24. 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.
Sat 5/28:12 am
IAD
-
ORD
1 stop8h 11m
Frontier
Tue 5/261:50 pm
ORD
-
IAD
1 stop8h 19m
Frontier
Deal found 4/24$226

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 April 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$219
(Kiwi.com)

One-way from

$100
(Super.com)

Popular in

January

Cheapest in

October

Average price

$351

Good round-trip deal

$367 or less

Good one-way deal

$223 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. 6% potential increase in price ($22 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 April 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 April 27, 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 5/30

6:08 am-9:59 am

1 stop4h 51m

Chicago Midway

Mon 6/1

9:22 am-4:31 pm

1 stop6h 09m

$243

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 8/20

6:00 am-9:50 am

1 stop4h 50m

Chicago Midway

Sat 8/22

9:30 am-4:25 pm

1 stop5h 55m

$243

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 6/24

5:29 pm-8:31 pm

1 stop4h 02m

Chicago O'Hare Intl

Thu 7/2

6:05 am-11:48 am

1 stop4h 43m

$253

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 6/16

8:29 am-12:00 pm

1 stop4h 31m

Chicago Midway

Thu 6/18

11:05 am-4:47 pm

1 stop4h 42m

$253

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 6/8

6:10 am-7:27 am

Nonstop2h 17m

Chicago O'Hare Intl

Sat 6/20

6:12 pm-9:22 pm

Nonstop2h 10m

$256

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 6/3

8:15 am-9:36 am

Nonstop2h 21m

Chicago O'Hare Intl

Tue 6/9

9:40 pm-12:45 am

Nonstop2h 05m

$257

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 6/3

11:58 am-5:56 pm

1 stop6h 58m

Chicago Midway

Thu 6/4

10:59 am-6:43 pm

1 stop6h 44m

$261

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 6/4

8:40 am-11:39 am

1 stop3h 59m

Chicago O'Hare Intl

Tue 6/9

11:03 am-2:08 pm

Nonstop2h 05m

$275

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 6/9

6:00 am-12:00 pm

1 stop7h 00m

Chicago Midway

Thu 6/11

12:45 pm-9:04 pm

1 stop7h 19m

$284

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 6/9

6:00 am-1:09 pm

1 stop8h 09m

Chicago Midway

Sat 6/13

6:35 pm-11:14 pm

1 stop3h 39m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 43 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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

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

Booking 81 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 month to book a flight from Washington, D.C. Dulles Intl Airport to Chicago?

Currently, January is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $38). Flying from Washington, D.C. Dulles Intl Airport to Chicago in March is currently the most expensive (average of $197). 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 April 27, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 8% on flights from Washington, D.C. Dulles Intl Airport to Chicago by exploring options for tickets in the evening.

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 April 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.

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

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 April 27, 2026.
See what other customers who have flown with Delta,United Airlines, andFrontier 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.
Delta
7.9
Good
8,463 reviews

Entertainment

7.8

Overall

7.9

Crew

8.5

Boarding

8.1

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,463 reviews
Delta
7.9
Good
8,463 reviews

Entertainment

7.8

Overall

7.9

Crew

8.5

Boarding

8.1

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,668 reviews
Delta
7.9
Good
8,463 reviews

Entertainment

7.8

Overall

7.9

Crew

8.5

Boarding

8.1

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.7
Fair
2,972 reviews
Delta
7.9
Good
8,463 reviews

Entertainment

7.8

Overall

7.9

Crew

8.5

Boarding

8.1

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 17m. Your travel time can differ by up to 2h 34m. 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 $207, respectively. These flights start at 71% 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: CommutAir (100%), ANA (78%), Ethiopian Air( 77%).

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

    On average you can expect to pay $810 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $139 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, January is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $38). Flying from Washington, D.C. Dulles Intl Airport to Chicago in March is currently the most expensive (average of $197). 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
Hammond
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 April 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$195FlexibilityNo cancel feeOn-time62%
DeltaCheapest$149Average$342FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$207Average$369FlexibilityNo cancel feeOn-time69%

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