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$76+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
1 adult, Economy
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Cheapflights Tip: The best prices from Washington, D.C. Dulles Intl to Chicago are usually found in September or August, booked 53 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap 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 October 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$140
(Kiwi.com)

One-way from

$76
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$282

Good round-trip deal

$296 or less

Good one-way deal

$184 or less
Provider with most accurate pricing for Washington, D.C. Dulles Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Washington, D.C. Dulles Intl-Chicago (CHI) flights.
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From Washington, D.C. Dulles Intl to Chicago (CHI)
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One-way flight from Washington, D.C. Dulles Intl to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Washington, D.C. Dulles Intl to Chicago (CHI).
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Price to beat on a one-way flight from Washington, D.C. Dulles Intl to Chicago (CHI).
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Find 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 October 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/4. 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 12/66:00 amIAD - MDW
1 stop18h 05mFrontier
Tue 12/98:00 amMDW - IAD
1 stop13h 19mFrontier
Deal found 10/4$140
This Cheapflightsfares deal was found by Cheapflights users on 10/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:00 amIAD - ORD
1 stop5h 41mFrontier
Sat 11/155:45 pmORD - IAD
1 stop5h 10mFrontier
Deal found 10/3$143
This Cheapflightsfares deal was found by Cheapflights users on 10/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/175:58 pmIAD - MDW
1 stop5h 13mFrontier
Wed 11/191:56 pmMDW - IAD
1 stop5h 24mFrontier
Deal found 10/3$143
This Frontier deal was found by Cheapflights users on 10/3. 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.
Fri 10/316:00 amIAD - ORD
1 stop5h 41mFrontier
Wed 11/512:37 pmORD - IAD
1 stop6h 43mFrontier
Deal found 10/3$144
This Frontier deal was found by Cheapflights users on 10/3. 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 10/298:47 amIAD - MDW
1 stop4h 54mFrontier
Wed 11/52:06 pmMDW - IAD
1 stop5h 14mFrontier
Deal found 10/3$144
This Booking.com deal was found by Cheapflights users on 10/3. 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.
Fri 10/249:58 pmIAD - ORD
1 stop21h 35mFrontier
Wed 10/2912:37 pmORD - IAD
1 stop6h 43mFrontier
Deal found 10/3$145
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/229:00 amIAD - ORD
1 stop5h 47mFrontier
Tue 10/2812:37 pmORD - IAD
1 stop6h 43mFrontier
Deal found 10/6$146
This Booking.com deal was found by Cheapflights users on 10/3. 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.
Thu 10/309:52 pmIAD - MDW
1 stop17h 30mFrontier
Sun 11/210:12 amMDW - IAD
1 stop8h 39mFrontier
Deal found 10/3$146
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/254:22 pmIAD - ORD
1 stop8h 07mFrontier
Tue 10/2812:37 pmORD - IAD
1 stop6h 43mFrontier
Deal found 10/6$148
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/229:00 amIAD - MDW
1 stop5h 38mFrontier
Wed 10/292:06 pmMDW - IAD
1 stop5h 14mFrontier
Deal found 10/5$148
This Frontier deal was found by Cheapflights users on 10/3. 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 10/306:00 amIAD - ORD
1 stop5h 41mFrontier
Wed 11/512:37 pmORD - IAD
1 stop6h 43mFrontier
Deal found 10/3$149
This Kiwi.com deal was found by Cheapflights users on 10/5. 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.
Fri 10/316:00 amIAD - MDW
1 stop13h 39mFrontier
Sat 11/11:37 pmMDW - IAD
1 stop9h 18mFrontier
Deal found 10/5$149

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 October 6, 2025.
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

Tue 10/28

8:47 am-12:41 pm

1 stop28h 54m

Chicago Midway

Tue 11/11

1:56 pm-8:20 pm

1 stop5h 24m

$143

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 11/2

8:36 pm-8:32 am

1 stop12h 56m

Chicago Midway

Thu 11/6

1:37 pm-12:11 am

1 stop9h 34m

$144

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 11/10

5:44 pm-10:11 pm

1 stop5h 27m

Chicago Midway

Fri 11/14

6:15 am-4:34 pm

1 stop9h 19m

$151

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 10/25

12:54 pm-11:20 pm

1 stop11h 26m

Chicago Midway

Mon 10/27

9:45 am-6:45 pm

1 stop8h 00m

$163

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 11/2

10:54 pm-12:30 am

1 stop26h 36m

Chicago Midway

Tue 11/4

1:56 pm-8:20 pm

1 stop5h 24m

$164

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 11/6

5:34 pm-10:03 pm

1 stop5h 29m

Chicago Midway

Mon 11/10

6:15 am-4:34 pm

1 stop9h 19m

$183

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 10/30

9:52 pm-2:22 pm

1 stop17h 30m

Chicago Midway

Sun 11/2

10:12 am-7:51 pm

1 stop8h 39m

$186

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 11/13

5:34 pm-10:03 pm

1 stop5h 29m

Chicago Midway

Sun 11/16

1:37 pm-12:11 am

1 stop9h 34m

$196

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 10/24

9:58 pm-10:21 am

1 stop13h 23m

Chicago Midway

Sun 10/26

6:20 am-3:30 pm

1 stop8h 10m

$196

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 11/14

5:34 pm-10:08 pm

1 stop5h 34m

Chicago Midway

Sun 11/16

1:37 pm-12:11 am

1 stop9h 34m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/3

Showing 1-10 of 45 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 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 October 3, 2025.

Booking 53 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 $122). Flying from Washington, D.C. Dulles Intl Airport to Chicago in January is currently the most expensive (average of $210). 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 October 6, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 36% 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 December 16, 2024.

Travelers seeking maximum savings on their Washington, D.C. Dulles Intl Airport to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Monday 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 October 6, 2025.

The most flights from IAD to CHI are scheduled on a Monday (30 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (27 on average).

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

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Dulles Intl Airport to Chicago trip
Airports
IAD

For quick check-in, locate your airline’s counter in the main terminal; they are arranged like an island with desks on both sides.

Read more about IADby Ramsey Qubein
ORD

Use the free shuttle train outside security to navigate between terminals at ORD, especially if arriving internationally at Terminal 5.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and IAD

Ramsey Qubein

Ramsey Qubein

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 October 6, 2025.
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
8.0
Very good
7,968 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,968 reviews
Delta
8.0
Very good
7,968 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,954 reviews
Delta
8.0
Very good
7,968 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Frontier
5.8
Fair
3,147 reviews
Delta
8.0
Very good
7,968 reviews

Food

7.3

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 11m. Your travel time can differ by up to 26h 43m. 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 United Airlines and Delta, with the lowest prices starting at $196 and $234, respectively. These flights start at 65% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Washington, D.C. Dulles Intl Airport to Chicago one-way?

    One-way options have recently been found by users for as low as $78 on Frontier. Other airlines that offer cheap prices include United Airlines from $105 and Delta from $115 one-way.

  • 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 (100%), Air China (94%), ANA( 82%).

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

    On average you can expect to pay $1,002 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $109 while the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) is currently priced at $180.

  • 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 $122). Flying from Washington, D.C. Dulles Intl Airport to Chicago in January is currently the most expensive (average of $210). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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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 October 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$196FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$196Average$340FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$327FlexibilityNo cancel feeOn-timeN/A

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