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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $106

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 5/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

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.
Multiple Airlines Logo
6:49 am - 7:51 pm
IAD
-
ORD
14h 02m
1 stop
Multiple Airlines Logo
7:33 pm - 5:27 pm
ORD
-
IAD
20h 54m
2 stops
$221Multiple Airlines
Sat, May 16 - Thu, May 21
Frontier Logo
7:27 pm - 2:12 pm
IAD
-
MDW
19h 45m
2 stops
Frontier Logo
6:00 am - 11:09 pm
MDW
-
IAD
16h 09m
1 stop
$221Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
11:07 am - 7:51 pm
IAD
-
ORD
9h 44m
1 stop
Frontier Logo
1:50 pm - 11:09 pm
ORD
-
IAD
8h 19m
1 stop
$222Frontier
Wed, Jun 3 - Fri, Jun 5
Frontier Logo
11:07 am - 10:02 pm
IAD
-
MDW
11h 55m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
IAD
9h 21m
1 stop
$222Frontier
Thu, May 28 - Sun, May 31
Multiple Airlines Logo
11:07 am - 10:02 pm
IAD
-
MDW
11h 55m
1 stop
Multiple Airlines Logo
2:47 pm - 2:18 pm
MDW
-
IAD
22h 31m
1 stop
$223Multiple Airlines
Tue, May 26 - Sun, May 31
Frontier Logo
11:07 am - 7:51 pm
IAD
-
ORD
9h 44m
1 stop
Frontier Logo
6:55 am - 5:12 pm
ORD
-
IAD
9h 17m
1 stop
$223Frontier
Thu, May 7 - Mon, May 11
Frontier Logo
8:57 pm - 8:03 am
IAD
-
ORD
12h 06m
1 stop
Frontier Logo
6:55 am - 4:00 pm
ORD
-
IAD
8h 05m
1 stop
$224Frontier
Wed, Jul 1 - Sat, Jul 4
Frontier Logo
11:17 am - 10:11 pm
IAD
-
MDW
11h 54m
1 stop
Frontier Logo
6:00 am - 4:20 pm
MDW
-
IAD
9h 20m
1 stop
$224Frontier
Wed, Jul 1 - Tue, Jul 7
Delta Logo
7:38 pm - 11:59 pm
IAD
-
ORD
5h 21m
1 stop
Delta Logo
5:41 pm - 11:39 pm
ORD
-
IAD
4h 58m
1 stop
$228Delta
Wed, May 27 - Sat, May 30
Delta Logo
6:00 am - 1:19 pm
IAD
-
MDW
8h 19m
1 stop
Delta Logo
5:11 pm - 12:44 am
MDW
-
IAD
6h 33m
1 stop
$228Delta
Wed, Jun 3 - Wed, Jun 10

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

Our best Delta deals on Washington, D.C. Dulles Intl Airport to Chicago flight tickets
Delta
May 27
IAD5:33 pmWashington, D.C. Dulles Intl
7h 26m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 30
ORD5:41 pmChicago O'Hare Intl
4h 58m
1 stop
IAD11:39 pmWashington, D.C. Dulles Intl
$228
Delta
May 2
IAD3:00 pmWashington, D.C. Dulles Intl
6h 16m
1 stop
ORD8:16 pmChicago O'Hare Intl
May 4
ORD5:04 pmChicago O'Hare Intl
4h 59m
1 stop
IAD11:03 pmWashington, D.C. Dulles Intl
$245
Delta
May 19
IAD5:31 pmWashington, D.C. Dulles Intl
5h 56m
1 stop
ORD10:27 pmChicago O'Hare Intl
May 30
ORD6:07 amChicago O'Hare Intl
5h 11m
1 stop
IAD12:18 pmWashington, D.C. Dulles Intl
$248

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

Our best United Airlines deals on Washington, D.C. Dulles Intl Airport to Chicago flight tickets
United Airlines
May 24
IAD10:31 amWashington, D.C. Dulles Intl
2h 22m
ORD11:53 amChicago O'Hare Intl
May 27
ORD6:30 amChicago O'Hare Intl
1h 54m
IAD9:24 amWashington, D.C. Dulles Intl
$233
United Airlines
May 9
IAD8:20 amWashington, D.C. Dulles Intl
2h 17m
ORD9:37 amChicago O'Hare Intl
May 9
ORD9:35 pmChicago O'Hare Intl
1h 58m
IAD12:33 amWashington, D.C. Dulles Intl
$239
United Airlines
May 29
IAD10:15 pmWashington, D.C. Dulles Intl
2h 11m
ORD11:26 pmChicago O'Hare Intl
Jun 1
ORD9:40 pmChicago O'Hare Intl
2h 05m
IAD12:45 amWashington, D.C. Dulles Intl
$252

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 April 21, 2026.
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

Cheapest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/16

6:49 am-7:51 pm

1 stop14h 02m

Chicago O'Hare Intl

Thu 5/21

7:33 pm-5:27 pm

2 stops20h 54m

$221

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/28

7:27 pm-2:12 pm

2 stops19h 45m

Chicago Midway

Mon 6/1

6:00 am-11:09 pm

1 stop16h 09m

$221

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 6/3

11:07 am-7:51 pm

1 stop9h 44m

Chicago O'Hare Intl

Fri 6/5

1:50 pm-11:09 pm

1 stop8h 19m

$222

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/28

11:07 am-10:02 pm

1 stop11h 55m

Chicago Midway

Sun 5/31

6:00 am-4:21 pm

1 stop9h 21m

$222

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 5/26

11:07 am-10:02 pm

1 stop11h 55m

Chicago Midway

Sun 5/31

2:47 pm-2:18 pm

1 stop22h 31m

$223

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 5/7

11:07 am-7:51 pm

1 stop9h 44m

Chicago O'Hare Intl

Mon 5/11

6:55 am-5:12 pm

1 stop9h 17m

$223

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 7/1

8:57 pm-8:03 am

1 stop12h 06m

Chicago O'Hare Intl

Sat 7/4

6:55 am-4:00 pm

1 stop8h 05m

$224

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 7/1

11:17 am-10:11 pm

1 stop11h 54m

Chicago Midway

Tue 7/7

6:00 am-4:20 pm

1 stop9h 20m

$224
Quickest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 5/27

7:38 pm-11:59 pm

1 stop5h 21m

Chicago O'Hare Intl

Sat 5/30

5:41 pm-11:39 pm

1 stop4h 58m

$228

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 6/3

6:00 am-1:19 pm

1 stop8h 19m

Chicago Midway

Wed 6/10

5:11 pm-12:44 am

1 stop6h 33m

$228

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 typical price of a round-trip flight between Washington, D.C. Dulles Intl Airport and Chicago?

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 $387. 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 $509.

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 $379. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $423.

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 $370 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 $201 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 10% 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 April 2026, prices for Washington, D.C. Dulles Intl Airport to Chicago flights are approximately 323% 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

$240

Fastest flight time

2h 03m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Washington, D.C. Dulles Intl Airport in the past 72 hours is $240. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago found on momondo in the last 72 hours is $368.
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 are 3 airports in Chicago. From Washington, D.C. Dulles Intl Airport there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Washington, D.C. Dulles Intl Airport to Chicago

  • 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 2h 03m, 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 $90Free CancellationRating
5.6
2,982 reviews
Search Frontier flights
DeltaPriceFrom $149Free CancellationRating
7.9
8,434 reviews
Search Delta flights
United AirlinesPriceFrom $207Free CancellationRating
7.4
9,613 reviews
Search United Airlines 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 35 times per week, with 9,613 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 $369 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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