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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $77

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 10/30. 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

Frontier Logo
6:15 am - 11:46 pmIAD-MDW
18h 31m1 stop
Frontier Logo
11:31 am - 8:53 pmMDW-IAD
8h 22m1 stop
$133Frontier
Find Deal
Thu, Oct 23 - Sat, Oct 25
Frontier Logo
8:40 am - 12:41 pmIAD-MDW
29h 01m1 stop
Frontier Logo
1:37 pm - 11:55 pmMDW-IAD
9h 18m1 stop
$134Frontier
Find Deal
Tue, Nov 4 - Sat, Nov 8
Frontier Logo
6:10 am - 10:31 amIAD-ORD
5h 21m1 stop
Frontier Logo
11:00 am - 7:46 pmORD-IAD
7h 46m1 stop
$135Frontier
Find Deal
Thu, Oct 2 - Tue, Oct 7
Frontier Logo
4:22 pm - 10:47 pmIAD-MDW
7h 25m1 stop
Frontier Logo
9:45 am - 7:14 pmMDW-IAD
8h 29m1 stop
$135Frontier
Find Deal
Sat, Oct 18 - Mon, Oct 20
Frontier Logo
9:00 am - 1:38 pmIAD-MDW
5h 38m1 stop
Frontier Logo
8:05 am - 7:46 pmMDW-IAD
10h 41m1 stop
$136Frontier
Find Deal
Wed, Oct 15 - Wed, Oct 22
Frontier Logo
6:10 am - 3:50 pmIAD-ORD
10h 40m1 stop
Frontier Logo
12:22 pm - 10:56 pmORD-IAD
9h 34m1 stop
$137Frontier
Find Deal
Fri, Oct 3 - Sat, Oct 4
Frontier Logo
5:58 pm - 12:11 amIAD-ORD
7h 13m1 stop
Frontier Logo
12:37 pm - 8:20 pmORD-IAD
6h 43m1 stop
$138Frontier
Find Deal
Mon, Nov 17 - Tue, Nov 18
Frontier Logo
9:15 am - 5:39 pmIAD-ORD
9h 24m1 stop
Frontier Logo
11:00 am - 7:46 pmORD-IAD
7h 46m1 stop
$143Frontier
Find Deal
Wed, Oct 1 - Tue, Oct 7
Multiple Airlines Logo
9:00 am - 1:47 pmIAD-ORD
5h 47m1 stop
Multiple Airlines Logo
6:54 pm - 9:38 pmORD-IAD
25h 44m1 stop
$184Multiple Airlines
Find Deal
Wed, Oct 22 - Sun, Oct 26
Multiple Airlines Logo
9:15 am - 5:39 pmIAD-ORD
9h 24m1 stop
Multiple Airlines Logo
8:56 pm - 10:56 pmORD-IAD
25h 00m2 stops
$187Multiple Airlines
Find Deal
Tue, Sep 30 - Fri, Oct 3

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
Oct 23
IAD6:15 amWashington, D.C. Dulles Intl
18h 31m
1 stop
MDW11:46 pmChicago Midway
Oct 25
MDW11:31 amChicago Midway
8h 22m
1 stop
IAD8:53 pmWashington, D.C. Dulles Intl
$133
Find similar
Frontier
Nov 4
IAD8:40 amWashington, D.C. Dulles Intl
29h 01m
1 stop
MDW12:41 pmChicago Midway
Nov 8
MDW1:37 pmChicago Midway
9h 18m
1 stop
IAD11:55 pmWashington, D.C. Dulles Intl
$134
Find similar
Frontier
Oct 2
IAD6:10 amWashington, D.C. Dulles Intl
5h 21m
1 stop
ORD10:31 amChicago O'Hare Intl
Oct 7
ORD11:00 amChicago O'Hare Intl
7h 46m
1 stop
IAD7:46 pmWashington, D.C. Dulles Intl
$135
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 September 19, 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 - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 10/23

6:15 am-11:46 pm

1 stop18h 31m

Chicago Midway

Sat 10/25

11:31 am-8:53 pm

1 stop8h 22m

$133

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 11/4

8:40 am-12:41 pm

1 stop29h 01m

Chicago Midway

Sat 11/8

1:37 pm-11:55 pm

1 stop9h 18m

$134

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 10/2

6:10 am-10:31 am

1 stop5h 21m

Chicago O'Hare Intl

Tue 10/7

11:00 am-7:46 pm

1 stop7h 46m

$135

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 10/18

4:22 pm-10:47 pm

1 stop7h 25m

Chicago Midway

Mon 10/20

9:45 am-7:14 pm

1 stop8h 29m

$135

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 10/15

9:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Wed 10/22

8:05 am-7:46 pm

1 stop10h 41m

$136

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 10/3

6:10 am-3:50 pm

1 stop10h 40m

Chicago O'Hare Intl

Sat 10/4

12:22 pm-10:56 pm

1 stop9h 34m

$137

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 11/17

5:58 pm-12:11 am

1 stop7h 13m

Chicago O'Hare Intl

Tue 11/18

12:37 pm-8:20 pm

1 stop6h 43m

$138

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 10/1

9:15 am-5:39 pm

1 stop9h 24m

Chicago O'Hare Intl

Tue 10/7

11:00 am-7:46 pm

1 stop7h 46m

$143

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 10/22

9:00 am-1:47 pm

1 stop5h 47m

Chicago O'Hare Intl

Sun 10/26

6:54 pm-9:38 pm

1 stop25h 44m

$184

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 9/30

9:15 am-5:39 pm

1 stop9h 24m

Chicago O'Hare Intl

Fri 10/3

8:56 pm-10:56 pm

2 stops25h 00m

$187

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 August is, on average, the cheapest month to fly to Chicago from Washington, D.C. Dulles Intl Airport, with most prices found around $279. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Washington, D.C. Dulles Intl Airport to Chicago during September average around $287.

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 $498.

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 $336. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $434.

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 $329 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 $254 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 20% 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 September 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

$188

Fastest flight time

2h 05m

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 $188. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago found on momondo in the last 72 hours is $309.
The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago takes 2h 05m
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 5h 20m, 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 $105Free CancellationRating
5.8
3,171 reviews
Search Frontier flights
United AirlinesPriceFrom $195Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
DeltaPriceFrom $208Free CancellationRating
7.9
7,964 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 27 times per week, with 8,926 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 $195 (round-trip), much lower than the average airfare cost of $339 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