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 $181. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $195 and $197, respectively. These flights start at 42% 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 $85 on Frontier. Other airlines that offer cheap prices include Allegiant Air from $90 and Delta from $99 one-way.

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

On average you can expect to pay $734 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $95 while the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) is currently priced at $179.

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 (85%), Avianca( 82%).

What are the most popular airlines that fly from Washington, D.C. Dulles Intl Airport to Chicago?

The most popular airlines flying from Washington, D.C. Dulles Intl Airport to Chicago are American Airlines, Delta and Frontier. Something to consider prior to booking your flight.

What is the cheapest day to fly round-trip from Washington, D.C. Dulles Intl Airport to Chicago?

Travelers have found that booking a Thursday departure is the best way to save up to 29% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

What is the cheapest month to fly from Washington, D.C. Dulles Intl Airport to Chicago?

Due to multiple factors, expect to potentially pay more when booking in April. For low rates, September can be a great choice for travel to Chicago. Flights to Chicago from Washington, D.C. Dulles Intl Airport in September are about $254 on average during September, but can be found for as low as $63.

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 eDreams the most. eDreams 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.

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.

$85+ Flights from Washington, D.C. Dulles Intl Airport to Chicago - Compare & Save Big

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Washington, D.C. Dulles Intl to Chicago are usually found in July or January, booked 28 days in advance, depart on a Friday or Wednesday and return on a Friday

Cheap flight deals from Dulles Intl to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$181 (CheapOair)
One-way from	$85 (Trip.com)
Popular in	December
Cheapest in	July
Average price	$317
Good round-trip deal	$299 or less
Good one-way deal	$167 or less

Provider with most accurate pricing for Washington, D.C. Dulles Intl-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Washington, D.C. Dulles Intl-Chicago (CHI) flights.

Search Deals

From Washington, D.C. Dulles Intl to Chicago (CHI)

Search Deals

One-way flight from Washington, D.C. Dulles Intl to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 3% potential increase in price ($12 potential increase over avg. RT price).

Search Deals

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

Search Deals

Price to beat on a round-trip flight from Washington, D.C. Dulles Intl to Chicago (CHI).

Search Deals

Price to beat on a one-way flight from Washington, D.C. Dulles Intl to Chicago (CHI).

Search Deals

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 29, 2025.

Thu 5/157:31 amIAD - ORD

1 stop22h 39mFrontier

Sat 5/179:19 amORD - IAD

1 stop22h 25mFrontier

Deal found 4/29

$181

Thu 5/153:32 pmIAD - MDW

1 stop9h 07mFrontier

Sat 5/1710:48 amMDW - IAD

1 stop4h 46mFrontier

Deal found 4/29

$181

Fri 5/2310:18 pmIAD - ORD

Nonstop2h 12mUnited Airlines

Sun 5/259:31 pmORD - IAD

Nonstop1h 59mUnited Airlines

Deal found 4/29

$195

Tue 7/16:20 amIAD - ORD

1 stop6h 43mDelta

Tue 7/15:05 pmORD - IAD

1 stop4h 50mDelta

Deal found 4/29

$197

Sat 5/243:37 pmIAD - MDW

1 stop6h 36mDelta

Sun 5/256:00 amMDW - IAD

1 stop4h 41mDelta

Deal found 4/29

$197

Sat 7/1211:49 amIAD - ORD

1 stop6h 31mAmerican Airlines

Sat 7/126:25 pmORD - IAD

1 stop4h 33mAmerican Airlines

Deal found 4/29

$215

Thu 6/1212:40 pmIAD - ORD

1 stop7h 31mSun Country Air

Thu 6/196:17 pmORD - IAD

1 stop16h 02mSun Country Air

Deal found 4/29

$245

Sun 6/111:54 amIAD - ORD

2 stops33h 09mMultiple Airlines

Fri 6/65:20 pmORD - IAD

1 stop20h 12mMultiple Airlines

Deal found 4/28

$268

Thu 6/193:58 pmIAD - MDW

1 stop16h 17mAllegiant Air

Sun 6/2211:45 amMDW - IAD

2 stops25h 38mAllegiant Air

Deal found 4/29

$294

Thu 6/53:58 pmIAD - MDW

1 stop16h 17mMultiple Airlines

Mon 6/98:05 amMDW - IAD

3 stops26h 21mMultiple Airlines

Deal found 4/29

$314

Best flights from Dulles Intl to Chicago
Discover carefully curated flight deals from Dulles Intl to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 29, 2025.

Thu 5/157:31 amIAD - ORD

1 stop22h 39mFrontier

Sat 5/179:19 amORD - IAD

1 stop22h 25mFrontier

Deal found 4/29

$181

Fri 5/2310:18 pmIAD - ORD

Nonstop2h 12mUnited Airlines

Sat 5/245:53 pmORD - IAD

Nonstop1h 59mUnited Airlines

Deal found 4/29

$195

Tue 7/15:29 pmIAD - ORD

1 stop4h 55mDelta

Wed 7/211:00 amORD - IAD

1 stop4h 44mDelta

Deal found 4/29

$197

Sat 7/1211:49 amIAD - ORD

1 stop6h 31mAmerican Airlines

Sat 7/126:25 pmORD - IAD

1 stop4h 33mAmerican Airlines

Deal found 4/29

$215

Thu 6/1212:40 pmIAD - ORD

1 stop7h 31mSun Country Air

Thu 6/196:17 pmORD - IAD

1 stop16h 02mSun Country Air

Deal found 4/29

$245

Sun 6/111:54 amIAD - ORD

2 stops33h 09mMultiple Airlines

Fri 6/65:20 pmORD - IAD

1 stop20h 12mMultiple Airlines

Deal found 4/28

$268

Thu 6/193:58 pmIAD - MDW

1 stop16h 17mAllegiant Air

Sun 6/2211:45 amMDW - IAD

2 stops25h 38mAllegiant Air

Deal found 4/29

$294

Thu 5/153:32 pmIAD - MDW

1 stop9h 07mFrontier

Sat 5/1710:48 amMDW - IAD

1 stop4h 46mFrontier

Deal found 4/29

$181

Sat 5/243:37 pmIAD - MDW

1 stop6h 36mDelta

Sun 5/256:00 amMDW - IAD

1 stop4h 41mDelta

Deal found 4/29

$197

Thu 6/53:58 pmIAD - MDW

1 stop16h 17mMultiple Airlines

Mon 6/98:05 amMDW - IAD

3 stops26h 21mMultiple Airlines

Deal found 4/29

$314

Last-minute flights from Dulles Intl to Chicago
Discover last-minute flight deals from Dulles Intl to Chicago. Data last updated April 29, 2025 and is based on user searches.

Mon 5/53:32 pmIAD - MDW

1 stop9h 15mFrontier

Mon 5/128:30 amMDW - IAD

1 stop4h 53mFrontier

Deal found 4/28

$190

Tue 5/611:47 amIAD - ORD

1 stop5h 54mFrontier

Thu 5/156:00 amORD - IAD

1 stop7h 23mFrontier

Deal found 4/29

$190

Wed 5/75:24 pmIAD - ORD

1 stop3h 57mDelta

Thu 5/299:39 amORD - IAD

1 stop6h 06mDelta

Deal found 4/29

$359

Wed 5/75:02 amIAD - ORD

1 stop4h 59mAmerican Airlines

Mon 5/126:35 pmORD - IAD

1 stop4h 27mAmerican Airlines

Deal found 4/29

$419

Wed 5/76:00 amIAD - MDW

1 stop3h 40mDelta

Mon 5/126:38 pmMDW - IAD

1 stop4h 50mDelta

Deal found 4/28

$454

Fri 5/910:34 pmIAD - ORD

1 stop10h 09mUnited Airlines

Sat 5/1011:14 amORD - IAD

Nonstop1h 56mUnited Airlines

Deal found 4/29

$319

Fri 5/99:42 pmIAD - ORD

2 stops26h 47mMultiple Airlines

Mon 5/122:19 pmORD - IAD

3 stops20h 07mMultiple Airlines

Deal found 4/29

$343

Thu 5/157:31 amIAD - ORD

1 stop22h 39mFrontier

Sat 5/179:19 amORD - IAD

1 stop22h 25mFrontier

Deal found 4/29

$181

Thu 5/153:32 pmIAD - MDW

1 stop9h 07mFrontier

Sat 5/1710:48 amMDW - IAD

1 stop4h 46mFrontier

Deal found 4/29

$181

Sat 5/178:25 amIAD - MDW

3 stops27h 28mMultiple Airlines

Mon 5/199:42 amMDW - IAD

3 stops24h 44mMultiple Airlines

Deal found 4/29

$431

Tue 5/205:02 amIAD - ORD

1 stop6h 39mAmerican Airlines

Tue 5/206:35 pmORD - IAD

1 stop4h 27mAmerican Airlines

Deal found 4/29

$284

Fri 5/2310:18 pmIAD - ORD

Nonstop2h 12mUnited Airlines

Sun 5/259:31 pmORD - IAD

Nonstop1h 59mUnited Airlines

Deal found 4/29

$195

One-way flights from Dulles Intl to Chicago
Search for one-way flight options from Dulles Intl to Chicago. Find affordable one-way fares based on user searches. Data last updated April 29, 2025.

Sat 6/144:16 pmIAD - ORD

1 stop8h 58mFrontier

Deal found 4/29

$85

Sat 7/196:10 amIAD - MDW

1 stop17h 25mFrontier

Deal found 4/29

$85

Sun 6/83:58 pmIAD - MDW

1 stop16h 17mAllegiant Air

Deal found 4/29

$90

Sat 5/242:10 pmIAD - ORD

1 stop8h 11mDelta

Deal found 4/29

$99

Thu 5/296:00 amIAD - MDW

1 stop3h 40mDelta

Deal found 4/29

$100

Fri 5/2310:18 pmIAD - ORD

Nonstop2h 12mUnited Airlines

Deal found 4/29

$115

Thu 6/1211:52 amIAD - ORD

1 stop6h 04mMultiple Airlines

Deal found 4/28

$118

Mon 6/1612:40 pmIAD - ORD

1 stop5h 41mSun Country Air

Deal found 4/29

$123

Sun 9/76:09 pmIAD - ORD

1 stop6h 48mAmerican Airlines

Deal found 4/29

$126

Sun 6/812:40 pmIAD - MDW

3 stops20h 42mMultiple Airlines

Deal found 4/29

$255

Sat 5/249:00 amIAD - ORD

2 stops15h 56mAlaska Airlines

Deal found 4/28

$303

Cheapflights Fare Finder

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

Fly to

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 5/15

7:31 am-5:10 am

1 stop22h 39m

Chicago O'Hare Intl

Sat 5/17

9:19 am-8:44 am

1 stop22h 25m

$181

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/15

3:32 pm-11:39 pm

1 stop9h 07m

Chicago Midway

Sat 5/17

10:48 am-4:34 pm

1 stop4h 46m

$181

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 5/23

10:18 pm-11:30 pm

Nonstop2h 12m

Chicago O'Hare Intl

Sun 5/25

9:31 pm-12:30 am

Nonstop1h 59m

$195

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 7/1

6:20 am-12:03 pm

1 stop6h 43m

Chicago O'Hare Intl

Tue 7/1

5:05 pm-10:55 pm

1 stop4h 50m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/24

3:37 pm-9:13 pm

1 stop6h 36m

Chicago Midway

Sun 5/25

6:00 am-11:41 am

1 stop4h 41m

$197

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 7/12

11:49 am-5:20 pm

1 stop6h 31m

Chicago O'Hare Intl

Sat 7/12

6:25 pm-11:58 pm

1 stop4h 33m

$215

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 6/12

12:40 pm-7:11 pm

1 stop7h 31m

Chicago O'Hare Intl

Thu 6/19

6:17 pm-11:19 am

1 stop16h 02m

$245

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 6/1

11:54 am-8:03 pm

2 stops33h 09m

Chicago O'Hare Intl

Fri 6/6

5:20 pm-2:32 pm

1 stop20h 12m

$268

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 6/19

3:58 pm-7:15 am

1 stop16h 17m

Chicago Midway

Sun 6/22

11:45 am-2:23 pm

2 stops25h 38m

$294

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 6/5

3:58 pm-7:15 am

1 stop16h 17m

Chicago Midway

Mon 6/9

8:05 am-11:26 am

3 stops26h 21m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 21 results

Compare providers for flights from Dulles Intl to Chicago

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.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy2 stars	Trust Score*3 stars
Gotogate	Price Accuracy3 stars	Trust Score*2 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 eDreams the most. eDreams 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

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.

Our travel experts

Ramsey Qubein

Expert on IAD

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?

Booking 28 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?

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?

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.

Rainfall in Chicago 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

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

Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Alaska Airlines, Delta and United 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.

Alaska Airlines

8.0

Very good

9,961 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Alaska Airlines

8.0

Very good

9,961 reviews

Alaska Airlines

8.0

Very good

9,961 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Delta

8.0

Very good

7,936 reviews

Alaska Airlines

8.0

Very good

9,961 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

United Airlines

7.4

Good

8,696 reviews

Alaska Airlines

8.0

Very good

9,961 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Allegiant Air

7.3

Good

734 reviews

Alaska Airlines

8.0

Very good

9,961 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

American Airlines

7.2

Good

10,000 reviews

Alaska Airlines

8.0

Very good

9,961 reviews

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

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 $181. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $195 and $197, respectively. These flights start at 42% 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 $85 on Frontier. Other airlines that offer cheap prices include Allegiant Air from $90 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 (85%), Avianca( 82%).
What are the cheapest flights from Washington, D.C. Dulles Intl Airport to Chicago?
On average you can expect to pay $734 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $95 while the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) is currently priced at $179.
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

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Lansing

Valparaiso

Chesterton

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Top 4 airlines flying from Dulles Intl to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$63	Average$118	FlexibilityNo cancel fee	On-time62%
United Airlines	Cheapest$161	Average$340	FlexibilityNo cancel fee	On-time69%
Delta	Cheapest$176	Average$264	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$364	Average$402	FlexibilityNo cancel fee	On-time71%

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$85+ 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 6/14. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Dulles Intl to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Washington, D.C. Dulles Intl to Chicago are usually found in July or January, booked 28 days in advance, depart on a Friday or Wednesday and return on a Friday

Cheap flight deals from Dulles Intl to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Dulles Intl to Chicago

Cheapest flights from Dulles Intl to ChicagoExplore 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 29, 2025.

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 29, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Washington, D.C. Dulles Intl Airport to Chicago that are best for you.

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.

The best insider tips for Washington, D.C. Dulles Intl Airport to Chicago flights

Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Dulles Intl Airport to Chicago trip

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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.

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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 25, 2025.

What is the cheapest month to book a flight from Washington, D.C. Dulles Intl Airport to Chicago?

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 29, 2025.

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.

Rainfall in Chicago by month

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

Temperature in Chicago by month

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

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Alaska Airlines, Delta and United 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.

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?

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

What are the most reliable airlines from Washington, D.C. Dulles Intl Airport to Chicago?

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

Can I find deals for flights from Dulles Intl to Chicago that include hotel bookings?

How can I find direct flights from Dulles Intl to Chicago?

Can I find deals for business class flights from Dulles Intl to Chicago?

What is the cheapest month to book a flight from Washington, D.C. Dulles Intl Airport to Chicago?

Traveling to a place near Washington, D.C. Dulles Intl Airport?

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Alternative routes for Dulles Intl to Chicago

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Top 4 airlines flying from Dulles Intl to Chicago

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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 29, 2025.