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$84+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Apr 16 — Apr 231
Wed 4/16
Wed 4/23
1 adult, Economy
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Cheapflights Tip: The best prices from Washington, D.C. Dulles Intl to Chicago are usually found in July or January, booked 66 days in advance, depart on a Friday or Wednesday 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 April 11, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$84
(Mytrip)

Popular in

December

Cheapest in

July

Average price

$313

Good round-trip deal

$315 or less

Good one-way deal

$164 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. 3% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 11, 2025.

This United Airlines deal was found by Cheapflights users on 4/10. 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.
Wed 5/283:35 pmIAD - ORD
Nonstop2h 13mUnited Airlines
Sat 5/319:31 pmORD - IAD
Nonstop1h 59mUnited Airlines
Deal found 4/10$179
This CheapOair deal was found by Cheapflights users on 4/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/255:25 pmIAD - ORD
1 stop7h 11mFrontier
Mon 4/286:30 amORD - IAD
1 stop6h 52mFrontier
Deal found 4/10$180
This CheapOair deal was found by Cheapflights users on 4/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/249:08 amIAD - MDW
1 stop14h 18mFrontier
Sun 4/274:00 pmMDW - IAD
1 stop15h 18mFrontier
Deal found 4/10$180
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:00 pmIAD - ORD
1 stop6h 17mDelta
Sun 5/256:24 amORD - IAD
1 stop6h 02mDelta
Deal found 4/10$197
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/256:00 amIAD - MDW
1 stop3h 40mDelta
Fri 5/306:31 pmMDW - IAD
1 stop4h 57mDelta
Deal found 4/10$207
This Mytrip deal was found by Cheapflights users on 4/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/118:30 amIAD - ORD
1 stop9h 45mMultiple Airlines
Thu 5/154:35 pmORD - IAD
2 stops27h 22mMultiple Airlines
Deal found 4/10$296
This Mytrip deal was found by Cheapflights users on 4/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/33:53 pmIAD - MDW
1 stop16h 20mAllegiant Air
Sun 7/611:37 amMDW - IAD
2 stops25h 46mAllegiant Air
Deal found 4/9$317
This Sun Country Air deal was found by Cheapflights users on 4/10. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2812:45 pmIAD - ORD
1 stop7h 27mSun Country Air
Sun 8/316:16 pmORD - IAD
1 stop16h 34mSun Country Air
Deal found 4/10$325
This Kissandfly.com deal was found by Cheapflights users on 4/10. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/108:25 amIAD - ORD
3 stops13h 35mSouthern / Mokulele
Sun 5/118:50 amORD - IAD
Nonstop1h 59mSouthern / Mokulele
Deal found 4/10$328
This American Airlines deal was found by Cheapflights users on 4/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/209:10 amIAD - ORD
1 stop6h 00mAmerican Airlines
Sun 6/225:29 amORD - IAD
1 stop6h 09mAmerican Airlines
Deal found 4/10$349
This Mytrip deal was found by Cheapflights users on 4/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/33:53 pmIAD - MDW
1 stop16h 20mMultiple Airlines
Sun 7/611:37 amMDW - IAD
3 stops27h 38mMultiple Airlines
Deal found 4/9$380

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 11, 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 - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 5/28

3:35 pm-4:48 pm

Nonstop2h 13m

Chicago O'Hare Intl

Sat 5/31

9:31 pm-12:30 am

Nonstop1h 59m

$179

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 4/25

5:25 pm-11:36 pm

1 stop7h 11m

Chicago O'Hare Intl

Mon 4/28

6:30 am-2:22 pm

1 stop6h 52m

$180

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 4/24

9:08 am-10:26 pm

1 stop14h 18m

Chicago Midway

Sun 4/27

4:00 pm-8:18 am

1 stop15h 18m

$180

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/24

6:00 pm-11:17 pm

1 stop6h 17m

Chicago O'Hare Intl

Sun 5/25

6:24 am-1:26 pm

1 stop6h 02m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 5/25

6:00 am-8:40 am

1 stop3h 40m

Chicago Midway

Fri 5/30

6:31 pm-12:28 am

1 stop4h 57m

$207

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 5/11

8:30 am-5:15 pm

1 stop9h 45m

Chicago O'Hare Intl

Thu 5/15

4:35 pm-8:57 pm

2 stops27h 22m

$296

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 7/3

3:53 pm-7:13 am

1 stop16h 20m

Chicago Midway

Sun 7/6

11:37 am-2:23 pm

2 stops25h 46m

$317

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 5/1

9:10 am-12:23 pm

1 stop4h 13m

Chicago O'Hare Intl

Sun 5/4

8:27 am-4:22 pm

1 stop6h 55m

$325

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/10

8:25 am-9:00 pm

3 stops13h 35m

Chicago O'Hare Intl

Sun 5/11

8:50 am-11:49 am

Nonstop1h 59m

$328

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 7/3

3:53 pm-7:13 am

1 stop16h 20m

Chicago Midway

Sun 7/6

11:37 am-4:15 pm

3 stops27h 38m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

Showing 1-10 of 21 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
GotogatePrice 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.

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 early departures, use the Aerotrain for quick access to gates. Security lines can be long, so arrive early.

Read more about IADby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on 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

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 April 4, 2025.

Booking 66 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, August is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $245). Flying from Washington, D.C. Dulles Intl Airport to Chicago in March is currently the most expensive (average of $321). 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 11, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 45% 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 Wednesday evenings when fares are most often at their lowest. Sunday afternoons 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 April 11, 2025.

The most flights from IAD to CHI are scheduled on a Wednesday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 11, 2025.
Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Delta, United Airlines and Allegiant Air. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,911 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,911 reviews
Delta
8.0
Very good
7,911 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,636 reviews
Delta
8.0
Very good
7,911 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Allegiant Air
7.3
Good
734 reviews
Delta
8.0
Very good
7,911 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,911 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Sun Country Air
6.9
Okay
349 reviews
Delta
8.0
Very good
7,911 reviews

Overall

8.0

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

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

    Flying on United Airlines is currently your cheapest option to Chicago, with prices starting at $179. Additional round-trip tickets that might be worth considering are offered by Frontier and Delta, with the lowest prices starting at $180 and $197, respectively. These flights start at 43% 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 $84 on Frontier. Other airlines that offer cheap prices include Delta from $99 and Allegiant Air from $101 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: Sun Country Air (100%), Copa Airlines (84%), Avianca( 84%).

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

    On average you can expect to pay $745 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $114 while the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) is currently priced at $160.

  • 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, August is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $245). Flying from Washington, D.C. Dulles Intl Airport to Chicago in March is currently the most expensive (average of $321). 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 Washington, D.C. Dulles Intl Airport?

Book flights to Washington, D.C. Dulles Intl Airport if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 4 airlines flying from Dulles Intl to Chicago

Discover the top 4 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$63Average$118FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$280FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$188Average$372FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$364Average$402FlexibilityNo cancel feeOn-time71%

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