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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $75

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington, D.C. Dulles Intl Airport to Chicago departing on 12/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Washington, D.C. Dulles Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:45 am - 5:27 pmIAD-ORD
12h 42m1 stop
Frontier Logo
8:00 am - 2:29 pmORD-IAD
5h 29m1 stop
$143Frontier
Find Deal
Mon, Dec 8 - Wed, Dec 10
Frontier Logo
5:45 am - 6:08 pmIAD-MDW
13h 23m1 stop
Frontier Logo
6:00 am - 11:05 pmMDW-IAD
16h 05m1 stop
$143Frontier
Find Deal
Thu, Dec 11 - Sat, Dec 13
Multiple Airlines Logo
6:00 am - 12:08 pmIAD-ORD
7h 08m1 stop
Multiple Airlines Logo
8:51 pm - 2:18 pmORD-IAD
16h 27m2 stops
$145Multiple Airlines
Find Deal
Tue, Jan 13 - Thu, Jan 15
Multiple Airlines Logo
6:00 am - 4:52 pmIAD-ORD
11h 52m1 stop
Multiple Airlines Logo
5:32 pm - 4:28 pmORD-IAD
21h 56m2 stops
$146Multiple Airlines
Find Deal
Wed, Jan 14 - Wed, Jan 21
Frontier Logo
5:41 pm - 10:21 pmIAD-MDW
5h 40m1 stop
Frontier Logo
9:15 am - 8:56 pmMDW-IAD
10h 41m1 stop
$146Frontier
Find Deal
Fri, Jan 9 - Sun, Jan 11
Frontier Logo
6:58 pm - 3:12 pmIAD-ORD
21h 14m1 stop
Frontier Logo
6:00 am - 6:16 pmORD-IAD
11h 16m1 stop
$147Frontier
Find Deal
Mon, Dec 15 - Thu, Dec 18
Frontier Logo
6:58 pm - 8:46 amIAD-MDW
14h 48m1 stop
Frontier Logo
6:12 am - 6:16 pmMDW-IAD
11h 04m1 stop
$147Frontier
Find Deal
Mon, Dec 15 - Thu, Dec 18
Frontier Logo
9:00 am - 6:46 pmIAD-ORD
10h 46m1 stop
Frontier Logo
8:45 am - 8:31 amORD-IAD
22h 46m1 stop
$151Frontier
Find Deal
Wed, Dec 10 - Sun, Dec 14
Multiple Airlines Logo
5:45 am - 11:54 amIAD-ORD
7h 09m1 stop
Multiple Airlines Logo
7:41 pm - 11:38 amORD-IAD
38h 57m2 stops
$152Multiple Airlines
Find Deal
Sat, Dec 13 - Tue, Dec 16
Multiple Airlines Logo
6:00 am - 12:08 pmIAD-ORD
7h 08m1 stop
Multiple Airlines Logo
10:48 am - 7:58 pmORD-IAD
8h 10m1 stop
$153Multiple Airlines
Find Deal
Tue, Jan 13 - Fri, Jan 16

Frontier flights from Washington, D.C. Dulles Intl Airport to Chicago

Our best Frontier deals on Washington, D.C. Dulles Intl Airport to Chicago flight tickets
Frontier
Dec 8
IAD5:45 amWashington, D.C. Dulles Intl
12h 42m
1 stop
ORD5:27 pmChicago O'Hare Intl
Dec 10
ORD8:00 amChicago O'Hare Intl
5h 29m
1 stop
IAD2:29 pmWashington, D.C. Dulles Intl
$143
Find similar
Frontier
Dec 10
IAD9:00 amWashington, D.C. Dulles Intl
29h 01m
2 stops
MDW1:01 pmChicago Midway
Dec 13
MDW6:00 amChicago Midway
16h 05m
1 stop
IAD11:05 pmWashington, D.C. Dulles Intl
$145
Find similar
Frontier
Jan 8
IAD6:00 amWashington, D.C. Dulles Intl
6h 31m
1 stop
MDW11:31 amChicago Midway
Jan 11
MDW9:15 amChicago Midway
10h 41m
1 stop
IAD8:56 pmWashington, D.C. Dulles Intl
$146
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Washington, D.C. Dulles Intl Airport 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, momondo users made 832,500 searches. Data last updated December 1, 2025.
Use the filters below to find and compare flights from Washington, D.C. Dulles Intl Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 12/8

5:45 am-5:27 pm

1 stop12h 42m

Chicago O'Hare Intl

Wed 12/10

8:00 am-2:29 pm

1 stop5h 29m

$143

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 12/11

5:45 am-6:08 pm

1 stop13h 23m

Chicago Midway

Sat 12/13

6:00 am-11:05 pm

1 stop16h 05m

$143

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 1/13

6:00 am-12:08 pm

1 stop7h 08m

Chicago O'Hare Intl

Thu 1/15

8:51 pm-2:18 pm

2 stops16h 27m

$145

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 1/14

6:00 am-4:52 pm

1 stop11h 52m

Chicago O'Hare Intl

Wed 1/21

5:32 pm-4:28 pm

2 stops21h 56m

$146

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 1/9

5:41 pm-10:21 pm

1 stop5h 40m

Chicago Midway

Sun 1/11

9:15 am-8:56 pm

1 stop10h 41m

$146

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 12/15

6:58 pm-3:12 pm

1 stop21h 14m

Chicago O'Hare Intl

Thu 12/18

6:00 am-6:16 pm

1 stop11h 16m

$147

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 12/15

6:58 pm-8:46 am

1 stop14h 48m

Chicago Midway

Thu 12/18

6:12 am-6:16 pm

1 stop11h 04m

$147

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 12/10

9:00 am-6:46 pm

1 stop10h 46m

Chicago O'Hare Intl

Sun 12/14

8:45 am-8:31 am

1 stop22h 46m

$151

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 12/13

5:45 am-11:54 am

1 stop7h 09m

Chicago O'Hare Intl

Tue 12/16

7:41 pm-11:38 am

2 stops38h 57m

$152

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 1/13

6:00 am-12:08 pm

1 stop7h 08m

Chicago O'Hare Intl

Fri 1/16

10:48 am-7:58 pm

1 stop8h 10m

$153

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Washington, D.C. Dulles Intl Airport to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Washington, D.C. Dulles Intl Airport, with most prices found around $261. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Washington, D.C. Dulles Intl Airport to Chicago during September average around $265.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $380. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Washington, D.C. Dulles Intl Airport to Chicago for around $503.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. Dulles Intl Airport to Chicago during this time can be as low as $346. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $427.

What is the cheapest Washington, D.C. Dulles Intl to Chicago flight route?

Fly from Washington, D.C. Dulles Intl to Chicago O'Hare Intl for the best Washington, D.C. Dulles Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Washington, D.C. Dulles Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $331 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Washington, D.C. Dulles Intl Airport for as low as $216 on momondo.

What cabin class options are available on Washington, D.C. Dulles Intl to Chicago flights?

There are 4 cabin classes available to choose from on Washington, D.C. Dulles Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Washington, D.C. Dulles Intl Airport to Chicago flights?

You could potentially save up to 29% on your flight if you consider stops on a Washington, D.C. Dulles Intl Airport to Chicago flight.

How have Washington, D.C. Dulles Intl Airport to Chicago flight prices changed over time?

As of December 2025, prices for Washington, D.C. Dulles Intl Airport to Chicago flights are approximately 27% more expensive when compared to flights at the same time last year.

When to book flights from Washington, D.C. Dulles Intl Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. Dulles Intl Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Washington, D.C. Dulles Intl Airport to Chicago (IAD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. Dulles Intl Airport to Chicago

Best Price Found

$209

Fastest flight time

2h 03m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Washington, D.C. Dulles Intl Airport in the past 72 hours is $209. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago found on momondo in the last 72 hours is $334.
The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago takes 2h 03m
Direct flights go from Washington, D.C. Dulles Intl Airport to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • How far is Washington, D.C. Dulles Intl to Chicago by plane?

    The distance between Washington, D.C. Dulles Intl and Chicago is about 571.5 mi. Flights usually cover this in 4h 39m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Washington, D.C. Dulles Intl Airport to Chicago?

    Prices for flights from Washington, D.C. Dulles Intl Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Washington, D.C. Dulles Intl Airport to Chicago?

  • How old do you have to be to fly from Washington, D.C. Dulles Intl Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Washington, D.C. Dulles Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Washington, D.C. Dulles Intl Airport to Chicago?

  • What is the most popular airline from Washington, D.C. Dulles Intl Airport to Chicago?

Best airlines flying from Washington, D.C. Dulles Intl Airport to Chicago

Compare and see reviews for airlines that fly from Washington, D.C. Dulles Intl Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $122Free CancellationRating
5.8
3,094 reviews
Search Frontier flights
United AirlinesPriceFrom $207Free CancellationRating
7.4
9,065 reviews
Search United Airlines flights
DeltaPriceFrom $234Free CancellationRating
7.9
8,010 reviews
Search Delta flights

  • United Airlines Flights From Washington, D.C. Dulles Intl Airport to Chicago

    United Airlines flies from Washington, D.C. Dulles Intl Airport to Chicago around 15 times per week, with 9,063 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Washington, D.C. Dulles Intl Airport to Chicago in the last 72 hours was $207 (round-trip), much lower than the average airfare cost of $331 for United Airlines flights on this route.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Washington, D.C..

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Washington, D.C. which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Washington, D.C. to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Washington, D.C..

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Washington, D.C. are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport