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$67+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Find cheap flights from Dulles Intl to Chicago with Cheapflights

1. Tell us where you want to go

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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 83 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 January 26, 2026.

This Expedia deal was found by Cheapflights users on 1/25. 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.
Mon 2/2311:41 am
IAD
-
ORD
1 stop11h 58m
Frontier
Mon 3/25:05 am
ORD
-
IAD
1 stop10h 03m
Frontier
Deal found 1/25$148
This Expedia deal was found by Cheapflights users on 1/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:37 pm
IAD
-
MDW
1 stop6h 00m
Frontier
Mon 2/236:00 am
MDW
-
IAD
1 stop9h 08m
Frontier
Deal found 1/26$148
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/2810:29 am
IAD
-
ORD
1 stop13h 10m
Frontier
Mon 3/25:05 am
ORD
-
IAD
1 stop10h 03m
Frontier
Deal found 1/25$155
This Booking.com deal was found by Cheapflights users on 1/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:22 pm
IAD
-
MDW
1 stop6h 07m
Frontier
Mon 3/26:00 am
MDW
-
IAD
1 stop9h 08m
Frontier
Deal found 1/26$156
This Frontier deal was found by Cheapflights users on 1/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
IAD
-
ORD
1 stop5h 50m
Frontier
Thu 4/94:31 pm
ORD
-
IAD
1 stop7h 05m
Frontier
Deal found 1/24$160
This Frontier deal was found by Cheapflights users on 1/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/73:15 pm
IAD
-
MDW
1 stop5h 52m
Frontier
Sat 4/112:56 pm
MDW
-
IAD
1 stop8h 45m
Frontier
Deal found 1/24$160
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/2110:29 am
IAD
-
ORD
1 stop13h 10m
Multiple Airlines
Wed 2/256:51 pm
ORD
-
IAD
2 stops20h 52m
Multiple Airlines
Deal found 1/25$161
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Sun 2/229:07 pm
IAD
-
ORD
2 stops18h 33m
Frontier
Sun 3/15:05 am
ORD
-
IAD
1 stop28h 35m
Frontier
Deal found 1/25$162
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Tue 3/107:00 am
IAD
-
ORD
1 stop12h 41m
Frontier
Tue 3/179:28 am
ORD
-
IAD
1 stop13h 28m
Frontier
Deal found 1/24$163
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:22 pm
IAD
-
ORD
1 stop6h 17m
Multiple Airlines
Wed 2/256:51 pm
ORD
-
IAD
2 stops20h 52m
Multiple Airlines
Deal found 1/26$164
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/116:20 am
IAD
-
ORD
1 stop12h 37m
Frontier
Wed 3/189:28 am
ORD
-
IAD
1 stop13h 53m
Frontier
Deal found 1/24$165
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/116:20 am
IAD
-
MDW
1 stop16h 59m
Frontier
Wed 3/186:05 am
MDW
-
IAD
1 stop17h 16m
Frontier
Deal found 1/24$165

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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$148
(Expedia)

One-way from

$67
(Kiwi.com)

Popular in

January

Cheapest in

October

Average price

$405

Good round-trip deal

$342 or less

Good one-way deal

$246 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. 10% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 26, 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

Dulles Intl

Fly to

Chicago

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 2/23

11:41 am-10:29 pm

1 stop11h 48m

Chicago Midway

Sat 2/28

8:00 am-9:25 am

1 stop24h 25m

$160

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 3/12

8:15 am-5:44 pm

1 stop10h 29m

Chicago Midway

Thu 3/19

2:41 pm-12:31 am

1 stop8h 50m

$221

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 2/28

8:15 am-9:34 am

Nonstop2h 19m

Chicago O'Hare Intl

Tue 3/3

2:30 pm-5:30 pm

Nonstop2h 00m

$231

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 2/21

10:30 pm-11:43 pm

Nonstop2h 13m

Chicago O'Hare Intl

Mon 2/23

6:20 pm-9:18 pm

Nonstop1h 58m

$238

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 2/23

8:20 am-9:38 am

Nonstop2h 18m

Chicago O'Hare Intl

Sat 2/28

1:02 pm-4:05 pm

Nonstop2h 03m

$238

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/2

1:10 pm-2:28 pm

Nonstop2h 18m

Chicago O'Hare Intl

Wed 5/6

2:25 pm-5:28 pm

Nonstop2h 03m

$245

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 4/1

6:15 am-7:26 am

Nonstop2h 11m

Chicago O'Hare Intl

Sat 4/4

9:18 pm-12:15 am

Nonstop1h 57m

$245

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 4/25

6:15 am-7:26 am

Nonstop2h 11m

Chicago O'Hare Intl

Sat 4/25

9:18 pm-12:15 am

Nonstop1h 57m

$245

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 2/18

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Sat 2/21

9:34 am-4:28 pm

1 stop5h 54m

$251

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 2/28

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Tue 3/3

6:00 am-11:35 am

1 stop4h 35m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 40 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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?

Use this chart to determine the optimal time to book a round-trip flight from Dulles Intl to Chicago. Price data was last updated on January 23, 2026.

Booking 82 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, February is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $115). Flying from Washington, D.C. Dulles Intl Airport to Chicago in January is currently the most expensive (average of $225). 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 January 26, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 13% 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 February 16, 2025.

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.

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 January 26, 2026.

The most flights from IAD to CHI are scheduled on a Friday (20 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 on average).

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 January 26, 2026.
See what other customers who have flown with Delta, 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.
Delta
7.9
Good
8,113 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Entertainment

7.8

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
8,113 reviews
Delta
7.9
Good
8,113 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Entertainment

7.8

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
9,198 reviews
Delta
7.9
Good
8,113 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Entertainment

7.8

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
3,057 reviews
Delta
7.9
Good
8,113 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Entertainment

7.8

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?

    Frontier, United Airlines, and Delta can get you from Washington, D.C. Dulles Intl Airport to Chicago in just under 2h 19m. Your travel time can differ by up to 9h 29m. 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 $106. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $194 and $203, respectively. These flights start at 65% 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: Ethiopian Air (87%), Air China (86%), Egyptair( 85%).

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

    On average you can expect to pay $588 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $156 while the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) is currently priced at $152.

  • 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, February is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $115). Flying from Washington, D.C. Dulles Intl Airport to Chicago in January is currently the most expensive (average of $225). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Dulles Intl to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$195FlexibilityNo cancel feeOn-time62%
DeltaCheapest$194Average$327FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$203Average$337FlexibilityNo cancel feeOn-time69%

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