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$86+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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The best prices from Washington, D.C. Dulles Intl to Chicago are usually found in February or October, booked 78 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 January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$175
(Frontier)

One-way from

$86
(CheapOair)

Popular in

March

Cheapest in

February

Average price

$328

Good round-trip deal

$307 or less

Good one-way deal

$203 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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High demand for flights, 0% potential price rise
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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 January 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 January 30, 2025.

This Frontier deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/95:57 pmIAD - ORD
1 stop6h 36mFrontier
Thu 2/208:04 amORD - IAD
1 stop7h 59mFrontier
Deal found 1/28$176
This United Airlines deal was found by Cheapflights users on 1/29. 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 2/268:30 amIAD - ORD
Nonstop2h 18mUnited Airlines
Wed 3/54:10 pmORD - IAD
Nonstop1h 51mUnited Airlines
Deal found 1/29$177
This Gotogate deal was found by Cheapflights users on 1/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/85:41 pmIAD - MDW
1 stop5h 15mFrontier
Mon 3/172:51 pmMDW - IAD
1 stop21h 25mFrontier
Deal found 1/30$189
This Gotogate deal was found by Cheapflights users on 1/29. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1011:57 amIAD - ORD
1 stop7h 09mMultiple Airlines
Tue 4/159:32 amORD - IAD
1 stop7h 40mMultiple Airlines
Deal found 1/29$193
This Delta deal was found by Cheapflights users on 1/29. 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 2/206:00 amIAD - ORD
1 stop4h 16mDelta
Thu 2/275:45 amORD - IAD
1 stop5h 12mDelta
Deal found 1/29$197
This Delta deal was found by Cheapflights users on 1/29. 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 3/181:35 pmIAD - MDW
1 stop5h 27mDelta
Wed 3/199:25 amMDW - IAD
1 stop5h 58mDelta
Deal found 1/29$197
This Sun Country Air deal was found by Cheapflights users on 1/30. 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 7/312:40 pmIAD - ORD
1 stop7h 31mSun Country Air
Fri 7/48:05 pmORD - IAD
1 stop14h 38mSun Country Air
Deal found 1/30$275
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Thu 2/206:30 amIAD - ORD
1 stop5h 08mAmerican Airlines
Mon 2/244:40 pmORD - IAD
1 stop6h 13mAmerican Airlines
Deal found 1/30$292
This Mytrip deal was found by Cheapflights users on 1/30. 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 8/1012:40 pmIAD - MDW
2 stops22h 01mMultiple Airlines
Thu 8/1411:43 amMDW - IAD
2 stops23h 49mMultiple Airlines
Deal found 1/30$527

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 2/10

10:39 am-3:43 pm

1 stop6h 04m

Chicago Midway

Wed 2/19

8:12 am-2:39 pm

1 stop5h 27m

$175

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 2/9

5:57 pm-11:33 pm

1 stop6h 36m

Chicago O'Hare Intl

Thu 2/20

8:04 am-5:03 pm

1 stop7h 59m

$176

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 2/26

8:30 am-9:48 am

Nonstop2h 18m

Chicago O'Hare Intl

Wed 3/5

4:10 pm-7:01 pm

Nonstop1h 51m

$177

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 4/10

11:57 am-6:06 pm

1 stop7h 09m

Chicago O'Hare Intl

Tue 4/15

9:32 am-6:12 pm

1 stop7h 40m

$193

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 3/18

1:35 pm-6:02 pm

1 stop5h 27m

Chicago Midway

Wed 3/19

9:25 am-4:23 pm

1 stop5h 58m

$197

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 2/18

6:00 am-9:16 am

1 stop4h 16m

Chicago O'Hare Intl

Thu 2/20

6:45 am-11:48 am

1 stop4h 03m

$204

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 3/1

6:02 am-11:05 am

1 stop6h 03m

Chicago O'Hare Intl

Mon 3/3

6:14 pm-9:09 pm

Nonstop1h 55m

$212

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 7/3

12:40 pm-7:11 pm

1 stop7h 31m

Chicago O'Hare Intl

Fri 7/4

8:05 pm-11:43 am

1 stop14h 38m

$275

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 2/20

6:30 am-10:38 am

1 stop5h 08m

Chicago O'Hare Intl

Mon 2/24

4:40 pm-11:53 pm

1 stop6h 13m

$292

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 2/15

6:03 pm-7:09 am

1 stop14h 06m

$86

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 19 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
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.

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 January 24, 2025.

Booking 78 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 $325). 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 30, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 43% 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 Tuesday 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 January 30, 2025.

The most flights from IAD to CHI are scheduled on a Thursday (20 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 January 30, 2025.
Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Delta, United Airlines and American Airlines. 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
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
8,450 reviews
Delta
8.0
Very good
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
8,906 reviews
Delta
8.0
Very good
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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
386 reviews
Delta
8.0
Very good
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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

Spirit Airlines
6.3
Okay
8,083 reviews
Delta
8.0
Very good
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

8.0

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 $175. 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 46% 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 $86 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: Ethiopian Air (87%), ANA (82%), United Airlines( 80%).

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

    On average you can expect to pay $995 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $127 while the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) is currently priced at $165.

  • 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 $325). 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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$63Average$101FlexibilityNo cancel feeOn-time62%
DeltaCheapest$175Average$308FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$187Average$340FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$364Average$402FlexibilityNo cancel feeOn-time71%
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