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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $62

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 9/9. 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

United Airlines Logo
6:35 am - 7:46 amIAD-ORD
2h 11mnonstop
United Airlines Logo
10:43 am - 1:49 pmORD-IAD
2h 06mnonstop
$123United Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 10
United Airlines Logo
5:10 pm - 6:25 pmIAD-ORD
2h 15mnonstop
United Airlines Logo
11:40 am - 2:37 pmORD-IAD
1h 57mnonstop
$135United Airlines
Find Deal
Mon, Sep 22 - Wed, Sep 24
United Airlines Logo
10:10 pm - 11:15 pmIAD-ORD
2h 05mnonstop
United Airlines Logo
10:43 am - 1:49 pmORD-IAD
2h 06mnonstop
$140United Airlines
Find Deal
Wed, Sep 10 - Fri, Sep 12
United Airlines Logo
3:55 pm - 5:10 pmIAD-ORD
2h 15mnonstop
United Airlines Logo
9:31 pm - 12:32 amORD-IAD
2h 01mnonstop
$147United Airlines
Find Deal
Mon, Aug 25 - Mon, Aug 25
Frontier Logo
1:37 pm - 8:22 pmIAD-MDW
7h 45m1 stop
Frontier Logo
10:51 am - 8:48 pmMDW-IAD
8h 57m1 stop
$178Frontier
Find Deal
Sat, Aug 16 - Sat, Aug 23
Frontier Logo
7:14 pm - 9:18 amIAD-MDW
15h 04m1 stop
Frontier Logo
9:00 am - 7:55 pmMDW-IAD
9h 55m1 stop
$182Frontier
Find Deal
Sat, Sep 6 - Wed, Sep 10
Delta Logo
6:00 am - 10:19 amIAD-ORD
5h 19m1 stop
Delta Logo
7:10 am - 11:28 amORD-IAD
3h 18m1 stop
$197Delta
Find Deal
Sun, Sep 21 - Thu, Sep 25
Delta Logo
6:00 am - 9:40 amIAD-MDW
4h 40m1 stop
Delta Logo
6:00 am - 11:40 amMDW-IAD
4h 40m1 stop
$197Delta
Find Deal
Sun, Sep 21 - Thu, Sep 25
American Airlines Logo
6:00 am - 10:43 amIAD-ORD
5h 43m1 stop
American Airlines Logo
1:20 pm - 10:48 pmORD-IAD
8h 28m1 stop
$228American Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 3
American Airlines Logo
4:36 pm - 8:40 pmIAD-ORD
5h 04m1 stop
American Airlines Logo
10:10 pm - 11:01 amORD-IAD
11h 51m1 stop
$234American Airlines
Find Deal
Mon, Aug 25 - Mon, Aug 25

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
Sep 3
IAD6:35 amWashington, D.C. Dulles Intl
2h 11m
ORD7:46 amChicago O'Hare Intl
Sep 10
ORD10:43 amChicago O'Hare Intl
2h 06m
IAD1:49 pmWashington, D.C. Dulles Intl
$123
Find similar
United Airlines
Sep 22
IAD5:10 pmWashington, D.C. Dulles Intl
2h 15m
ORD6:25 pmChicago O'Hare Intl
Sep 24
ORD11:40 amChicago O'Hare Intl
1h 57m
IAD2:37 pmWashington, D.C. Dulles Intl
$135
Find similar
United Airlines
Sep 10
IAD10:10 pmWashington, D.C. Dulles Intl
2h 05m
ORD11:15 pmChicago O'Hare Intl
Sep 12
ORD10:43 amChicago O'Hare Intl
2h 06m
IAD1:49 pmWashington, D.C. Dulles Intl
$140
Find similar

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
Sep 21
IAD6:00 amWashington, D.C. Dulles Intl
5h 19m
1 stop
ORD10:19 amChicago O'Hare Intl
Sep 25
ORD7:10 amChicago O'Hare Intl
3h 18m
1 stop
IAD11:28 amWashington, D.C. Dulles Intl
$197
Find similar
Delta
Aug 26
IAD5:25 pmWashington, D.C. Dulles Intl
6h 12m
1 stop
ORD10:37 pmChicago O'Hare Intl
Sep 2
ORD7:15 amChicago O'Hare Intl
3h 17m
1 stop
IAD11:32 amWashington, D.C. Dulles Intl
$209
Find similar
Delta
Sep 12
IAD5:25 pmWashington, D.C. Dulles Intl
5h 11m
1 stop
MDW9:36 pmChicago Midway
Sep 16
MDW10:35 amChicago Midway
4h 52m
1 stop
IAD4:27 pmWashington, D.C. Dulles Intl
$230
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 August 5, 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

Wed 9/3

6:35 am-7:46 am

Nonstop2h 11m

Chicago O'Hare Intl

Wed 9/10

10:43 am-1:49 pm

Nonstop2h 06m

$123

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 9/22

5:10 pm-6:25 pm

Nonstop2h 15m

Chicago O'Hare Intl

Wed 9/24

11:40 am-2:37 pm

Nonstop1h 57m

$135

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 9/10

10:10 pm-11:15 pm

Nonstop2h 05m

Chicago O'Hare Intl

Fri 9/12

10:43 am-1:49 pm

Nonstop2h 06m

$140

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 8/25

3:55 pm-5:10 pm

Nonstop2h 15m

Chicago O'Hare Intl

Mon 8/25

9:31 pm-12:32 am

Nonstop2h 01m

$147

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 8/16

1:37 pm-8:22 pm

1 stop7h 45m

Chicago Midway

Sat 8/23

10:51 am-8:48 pm

1 stop8h 57m

$178

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/6

7:14 pm-9:18 am

1 stop15h 04m

Chicago Midway

Wed 9/10

9:00 am-7:55 pm

1 stop9h 55m

$182

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 9/21

6:00 am-10:19 am

1 stop5h 19m

Chicago O'Hare Intl

Thu 9/25

7:10 am-11:28 am

1 stop3h 18m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 9/21

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Thu 9/25

6:00 am-11:40 am

1 stop4h 40m

$197

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 9/3

6:00 am-10:43 am

1 stop5h 43m

Chicago O'Hare Intl

Wed 9/3

1:20 pm-10:48 pm

1 stop8h 28m

$228

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 8/25

4:36 pm-8:40 pm

1 stop5h 04m

Chicago O'Hare Intl

Mon 8/25

10:10 pm-11:01 am

1 stop11h 51m

$234

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 January is, on average, the cheapest month to fly to Chicago from Washington, D.C. Dulles Intl Airport, with most prices found around $299. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Washington, D.C. Dulles Intl Airport to Chicago during February average around $299.

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 $386. 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 $492.

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 $333. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $436.

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 $324 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 $271 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 August 2025, prices for Washington, D.C. Dulles Intl Airport to Chicago flights are approximately 4% cheaper 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

  • 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 05m, 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
5.8
3,232 reviews
Search Frontier flights
United AirlinesPriceFrom $161Free CancellationRating
7.4
8,912 reviews
Search United Airlines flights
DeltaPriceFrom $176Free CancellationRating
8.0
7,987 reviews
Search Delta flights
American AirlinesPriceFrom $388Free CancellationRating
7.2
10,000 reviews
Search American 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 27 times per week, with 8,912 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 $161 (round-trip), much lower than the average airfare cost of $266 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
Lansing
Portage
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