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$68+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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The best prices from Washington, D.C. Dulles Intl to Chicago are usually found in February or January, booked 78 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

February

Round-trip from

$141
(Booking.com)

One-way from

$68
(FlightHub)
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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High demand for flights, 16% potential price rise
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Best time to find cheap flights, 13% potential price drop
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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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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 November 20, 2024.

This CheapOair deal was found by Cheapflights users on 11/20. 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 12/155:57 pmIAD - ORD
1 stop16h 57mFrontier
Wed 12/186:55 amORD - IAD
1 stop8h 33mFrontier
Deal found 11/20$148
This Frontier deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/183:25 pmIAD - MDW
1 stop6h 52mFrontier
Wed 12/258:25 amMDW - IAD
1 stop5h 00mFrontier
Deal found 11/19$148
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Tue 12/1710:16 pmIAD - ORD
Nonstop2h 04mUnited Airlines
Wed 12/183:56 pmORD - IAD
Nonstop1h 54mUnited Airlines
Deal found 11/19$197
This Delta deal was found by Cheapflights users on 11/20. 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.
Wed 12/111:35 pmIAD - ORD
1 stop3h 55mDelta
Wed 12/185:40 amORD - IAD
1 stop5h 10mDelta
Deal found 11/20$216
This Delta deal was found by Cheapflights users on 11/19. 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 12/106:00 amIAD - MDW
1 stop3h 58mDelta
Wed 12/115:50 pmMDW - IAD
1 stop4h 35mDelta
Deal found 11/19$216
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/125:00 amIAD - ORD
1 stop4h 45mAmerican Airlines
Sat 12/1412:25 pmORD - IAD
1 stop6h 03mAmerican Airlines
Deal found 11/19$256
This Mytrip deal was found by Cheapflights users on 11/19. 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 12/199:15 pmIAD - ORD
2 stops28h 32mMultiple Airlines
Tue 1/213:22 pmORD - IAD
3 stops23h 48mMultiple Airlines
Deal found 11/19$364
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/208:00 amIAD - MDW
1 stop27h 41mMultiple Airlines
Tue 12/39:34 amMDW - IAD
1 stop27h 24mMultiple Airlines
Deal found 11/19$385
This CheapOair deal was found by Cheapflights users on 11/19. 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.
Tue 11/2612:33 pmIAD - ORD
1 stop6h 22mSun Country Air
Thu 11/289:20 amORD - IAD
1 stop25h 25mSun Country Air
Deal found 11/19$386
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Fri 12/137:00 amIAD - MDW
1 stop10h 40mPorter Airlines
Sun 12/1511:15 amMDW - IAD
1 stop10h 09mPorter Airlines
Deal found 11/19$526
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Fri 12/67:00 amIAD - MDW
1 stop10h 40mAir Transat
Sun 12/811:15 amMDW - IAD
1 stop10h 09mAir Transat
Deal found 11/19$707

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 1/10

11:32 am-7:17 pm

1 stop8h 45m

Chicago O'Hare Intl

Sun 1/12

4:11 pm-5:01 pm

1 stop23h 50m

$141

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 12/18

3:25 pm-9:17 pm

1 stop6h 52m

Chicago Midway

Wed 12/25

8:25 am-2:25 pm

1 stop5h 00m

$148

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 12/17

8:20 am-9:34 am

Nonstop2h 14m

Chicago O'Hare Intl

Tue 12/24

9:05 pm-11:59 pm

Nonstop1h 54m

$197

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 12/17

5:35 pm-8:28 pm

1 stop3h 53m

Chicago O'Hare Intl

Wed 12/18

3:40 pm-9:29 pm

1 stop4h 49m

$216

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 12/10

6:00 am-8:58 am

1 stop3h 58m

Chicago Midway

Tue 12/10

5:50 pm-11:25 pm

1 stop4h 35m

$216

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 12/12

5:00 am-8:45 am

1 stop4h 45m

Chicago O'Hare Intl

Sat 12/14

12:25 pm-7:28 pm

1 stop6h 03m

$256

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 4/3

11:00 am-5:29 pm

1 stop7h 29m

Chicago O'Hare Intl

Sun 4/6

8:00 pm-11:00 am

1 stop14h 00m

$275

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 12/19

9:15 pm-12:47 am

2 stops28h 32m

Chicago O'Hare Intl

Tue 1/21

3:22 pm-4:10 pm

3 stops23h 48m

$364

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 12/13

7:00 am-4:40 pm

1 stop10h 40m

Chicago Midway

Sun 12/15

11:15 am-10:24 pm

1 stop10h 09m

$526

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 12/23

12:45 pm-3:03 pm

3 stops27h 18m

Chicago Midway

Fri 12/27

11:15 am-10:24 pm

1 stop10h 09m

$563

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 26 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 November.
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*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 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 November 15, 2024.

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, September is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $232). Flying from Washington, D.C. Dulles Intl Airport to Chicago in June is currently the most expensive (average of $308). 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 November 20, 2024.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 23% 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 November 18, 2024.

Travelers seeking maximum savings on their Washington, D.C. Dulles Intl Airport to Chicago flight should consider departing on Monday afternoons when fares are most often at their lowest. Friday at noon 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 November 20, 2024.

The most flights from IAD to CHI are scheduled on a Tuesday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 November 20, 2024.
Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Frontier, United Airlines and Delta. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Porter Airlines
7.8
Good
288 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Air Transat
7.8
Good
389 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $141. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $197 and $216, respectively. These flights start at 55% 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 $68 on Frontier. Other airlines that offer cheap prices include United Airlines from $99 and Delta from $108 one-way.

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

    Before booking your flight to Chicago from Washington, D.C. Dulles Intl Airport, check out the most reliable airlines to get you to your destination on time: Egyptair (100%), ANA (93%), Ethiopian Air( 92%).

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

    On average you can expect to pay $906 for a flight from Washington, D.C. Dulles Intl Airport to Chicago. The cheapest flight overall is $88 while the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl) is currently priced at $197.

  • 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, September is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Chicago (average of $232). Flying from Washington, D.C. Dulles Intl Airport to Chicago in June is currently the most expensive (average of $308). 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.

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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$63Average$101FlexibilityNo cancel feeOn-time62%
DeltaCheapest$175Average$305FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$184Average$345FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$223Average$402FlexibilityNo cancel feeOn-time71%
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