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$73+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Mar 17 — Mar 241
Mon 3/17
Mon 3/24
1 adult, Economy
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The best prices from Washington, D.C. Dulles Intl to Chicago are usually found in January or February, booked 77 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 March 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$163
(CheapOair)

One-way from

$73
(CheapOair)

Popular in

December

Cheapest in

January

Average price

$369

Good round-trip deal

$298 or less

Good one-way deal

$149 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. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 12, 2025.

This CheapOair deal was found by Cheapflights users on 3/11. 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.
Sun 5/185:26 pmIAD - ORD
1 stop7h 06mFrontier
Sat 5/315:10 amORD - IAD
1 stop9h 54mFrontier
Deal found 3/11$163
This Flightnetwork deal was found by Cheapflights users on 3/12. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/19:14 amIAD - MDW
1 stop14h 26mFrontier
Mon 5/58:30 amMDW - IAD
1 stop4h 53mFrontier
Deal found 3/12$165
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Mon 4/710:20 pmIAD - ORD
Nonstop2h 09mUnited Airlines
Thu 4/105:59 pmORD - IAD
Nonstop2h 02mUnited Airlines
Deal found 3/12$177
This Delta deal was found by Cheapflights users on 3/12. 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.
Tue 4/155:32 pmIAD - ORD
1 stop7h 27mDelta
Wed 4/237:10 amORD - IAD
1 stop4h 51mDelta
Deal found 3/12$197
This Delta deal was found by Cheapflights users on 3/10. 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.
Thu 4/36:00 amIAD - MDW
1 stop3h 43mDelta
Thu 4/109:23 amMDW - IAD
1 stop5h 55mDelta
Deal found 3/10$197
This Booking.com deal was found by Cheapflights users on 3/12. 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.
Wed 4/164:29 pmIAD - ORD
1 stop23h 37mMultiple Airlines
Sun 4/207:05 pmORD - IAD
1 stop14h 38mMultiple Airlines
Deal found 3/12$206
This Sun Country Air deal was found by Cheapflights users on 3/12. 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 3/12$285
This American Airlines deal was found by Cheapflights users on 3/12. 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.
Wed 4/92:12 pmIAD - ORD
1 stop4h 28mAmerican Airlines
Mon 4/216:30 pmORD - IAD
1 stop13h 08mAmerican Airlines
Deal found 3/12$306
This KAYAK deal was found by Cheapflights users on 3/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/17:05 amIAD - ORD
1 stop10h 20mSouthwest
Fri 4/44:00 pmORD - IAD
1 stop7h 45mSouthwest
Deal found 3/12$310
This Mytrip deal was found by Cheapflights users on 3/12. 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 6/1212:40 pmIAD - MDW
2 stops32h 06mMultiple Airlines
Sun 6/158:50 amMDW - IAD
2 stops24h 30mMultiple Airlines
Deal found 3/12$402

Find flights from Dulles Intl to Chicago within your budget

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 March 12, 2025.

Fly from

Dulles Intl

Fly to

Chicago

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 5/18

5:26 pm-11:32 pm

1 stop7h 06m

Chicago O'Hare Intl

Sat 5/31

5:10 am-4:04 pm

1 stop9h 54m

$163

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/1

9:14 am-10:40 pm

1 stop14h 26m

Chicago Midway

Mon 5/5

8:30 am-2:23 pm

1 stop4h 53m

$165

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 4/7

10:20 pm-11:29 pm

Nonstop2h 09m

Chicago O'Hare Intl

Thu 4/10

5:59 pm-9:01 pm

Nonstop2h 02m

$177

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 4/15

5:23 pm-8:45 pm

1 stop4h 22m

Chicago O'Hare Intl

Wed 4/16

6:45 am-11:31 am

1 stop3h 46m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 4/3

6:00 am-8:43 am

1 stop3h 43m

Chicago Midway

Thu 4/10

9:23 am-4:18 pm

1 stop5h 55m

$197

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 4/15

8:34 pm-7:45 am

1 stop12h 11m

Chicago O'Hare Intl

Sun 4/20

7:05 pm-10:43 am

1 stop14h 38m

$199

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 8/28

12:45 pm-7:12 pm

1 stop7h 27m

Chicago O'Hare Intl

Sun 8/31

6:16 pm-11:50 am

1 stop16h 34m

$285

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 4/9

2:12 pm-5:40 pm

1 stop4h 28m

Chicago O'Hare Intl

Mon 4/21

6:30 pm-8:38 am

1 stop13h 08m

$306

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 4/1

7:05 am-4:25 pm

1 stop10h 20m

Chicago O'Hare Intl

Fri 4/4

4:00 pm-12:45 am

1 stop7h 45m

$310

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 6/12

12:40 pm-7:46 pm

2 stops32h 06m

Chicago Midway

Sun 6/15

8:50 am-10:20 am

2 stops24h 30m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/12

Showing 1-10 of 20 results
1
2

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 March.
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

Find out what our experts recommend to make the most of 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

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.

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.

Travel insights for flights from Dulles Intl to Chicago

Get recent, data-driven insights about flights from Dulles Intl to Chicago including ideal travel times, pricing trends, and more.

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 March 7, 2025.

Booking 77 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 $327). 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 March 12, 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 March 12, 2025.

The most flights from IAD to CHI are scheduled on a Wednesday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 March 12, 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
7,953 reviews

Entertainment

7.9

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

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
7,953 reviews
Delta
8.0
Very good
7,953 reviews

Entertainment

7.9

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

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
8,623 reviews
Delta
8.0
Very good
7,953 reviews

Entertainment

7.9

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

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
739 reviews
Delta
8.0
Very good
7,953 reviews

Entertainment

7.9

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

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
7,953 reviews

Entertainment

7.9

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

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
7.0
Good
357 reviews
Delta
8.0
Very good
7,953 reviews

Entertainment

7.9

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

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 Frontier is currently your cheapest option to Chicago, with prices starting at $163. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $177 and $197, respectively. These flights start at 49% 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 $73 on Frontier. Other airlines that offer cheap prices include United Airlines from $89 and Delta from $99 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%), Ethiopian Air (87%), ANA( 85%).

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

    On average you can expect to pay $4,475 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $89 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, 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 $327). 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 March 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$63Average$101FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$303FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$187Average$374FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$364Average$402FlexibilityNo cancel feeOn-time71%
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