Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 2/2. 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.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
10:29 am - 9:33 pm
IAD
-
MDW
12h 04m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$143Frontier
Sat, Feb 21 - Mon, Feb 23
Frontier Logo
11:39 am - 10:44 pm
IAD
-
ORD
12h 05m
1 stop
Frontier Logo
5:40 am - 4:28 pm
ORD
-
IAD
9h 48m
1 stop
$144Frontier
Sat, Feb 7 - Mon, Feb 9
Frontier Logo
10:29 am - 9:33 pm
IAD
-
MDW
12h 04m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$144Frontier
Sat, Feb 21 - Mon, Feb 23
Multiple Airlines Logo
3:58 pm - 8:18 am
IAD
-
ORD
17h 20m
1 stop
Multiple Airlines Logo
6:57 pm - 7:58 pm
ORD
-
IAD
24h 01m
1 stop
$145Multiple Airlines
Mon, Feb 2 - Thu, Feb 5
Frontier Logo
10:29 am - 9:33 pm
IAD
-
MDW
12h 04m
1 stop
Frontier Logo
6:00 am - 4:08 pm
MDW
-
IAD
9h 08m
1 stop
$145Frontier
Sat, Feb 21 - Mon, Feb 23
Frontier Logo
11:22 am - 10:29 pm
IAD
-
MDW
12h 07m
1 stop
Frontier Logo
9:04 pm - 10:40 am
MDW
-
IAD
12h 36m
1 stop
$149Frontier
Thu, Feb 26 - Sun, Mar 1
Frontier Logo
5:33 pm - 10:46 pm
IAD
-
ORD
6h 13m
1 stop
Frontier Logo
5:40 am - 4:28 pm
ORD
-
IAD
9h 48m
1 stop
$150Frontier
Mon, Jan 26 - Thu, Jan 29
Frontier Logo
5:33 pm - 10:19 pm
IAD
-
MDW
5h 46m
1 stop
Frontier Logo
6:20 am - 4:28 pm
MDW
-
IAD
9h 08m
1 stop
$150Frontier
Mon, Jan 26 - Thu, Jan 29
Frontier Logo
11:37 am - 10:39 pm
IAD
-
ORD
12h 02m
1 stop
Frontier Logo
8:30 am - 9:25 am
ORD
-
IAD
23h 55m
1 stop
$152Frontier
Sat, Feb 14 - Wed, Feb 18
Multiple Airlines Logo
5:33 pm - 11:22 am
IAD
-
ORD
18h 49m
2 stops
Multiple Airlines Logo
6:57 pm - 7:58 pm
ORD
-
IAD
24h 01m
1 stop
$154Multiple Airlines
Mon, Feb 2 - Thu, Feb 5

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
Feb 21
IAD10:29 amWashington, D.C. Dulles Intl
12h 04m
1 stop
MDW9:33 pmChicago Midway
Feb 23
MDW6:00 amChicago Midway
9h 08m
1 stop
IAD4:08 pmWashington, D.C. Dulles Intl
$143
Frontier
Feb 7
IAD11:39 amWashington, D.C. Dulles Intl
12h 05m
1 stop
ORD10:44 pmChicago O'Hare Intl
Feb 9
ORD5:40 amChicago O'Hare Intl
9h 48m
1 stop
IAD4:28 pmWashington, D.C. Dulles Intl
$144
Frontier
Feb 21
IAD10:29 amWashington, D.C. Dulles Intl
12h 04m
1 stop
MDW9:33 pmChicago Midway
Feb 23
MDW6:00 amChicago Midway
9h 08m
1 stop
IAD4:08 pmWashington, D.C. Dulles Intl
$145

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
Jan 27
IAD12:23 pmWashington, D.C. Dulles Intl
6h 22m
1 stop
ORD5:45 pmChicago O'Hare Intl
Feb 3
ORD6:15 amChicago O'Hare Intl
6h 20m
1 stop
IAD1:35 pmWashington, D.C. Dulles Intl
$347
Delta
Jan 27
IAD12:23 pmWashington, D.C. Dulles Intl
10h 12m
1 stop
ORD9:35 pmChicago O'Hare Intl
Jan 30
ORD7:01 amChicago O'Hare Intl
11h 08m
1 stop
IAD7:09 pmWashington, D.C. Dulles Intl
$353
Delta
Jan 22
IAD12:40 pmWashington, D.C. Dulles Intl
5h 49m
1 stop
MDW5:29 pmChicago Midway
Jan 26
MDW12:48 pmChicago Midway
4h 33m
1 stop
IAD6:21 pmWashington, D.C. Dulles Intl
$633

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 January 15, 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

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 2/21

10:29 am-9:33 pm

1 stop12h 04m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$143

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 2/7

11:39 am-10:44 pm

1 stop12h 05m

Chicago O'Hare Intl

Mon 2/9

5:40 am-4:28 pm

1 stop9h 48m

$144

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 2/21

10:29 am-9:33 pm

1 stop12h 04m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$144

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 2/2

3:58 pm-8:18 am

1 stop17h 20m

Chicago O'Hare Intl

Thu 2/5

6:57 pm-7:58 pm

1 stop24h 01m

$145

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 2/21

10:29 am-9:33 pm

1 stop12h 04m

Chicago Midway

Mon 2/23

6:00 am-4:08 pm

1 stop9h 08m

$145

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 2/26

11:22 am-10:29 pm

1 stop12h 07m

Chicago Midway

Sun 3/1

9:04 pm-10:40 am

1 stop12h 36m

$149

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 1/26

5:33 pm-10:46 pm

1 stop6h 13m

Chicago O'Hare Intl

Thu 1/29

5:40 am-4:28 pm

1 stop9h 48m

$150

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 1/26

5:33 pm-10:19 pm

1 stop5h 46m

Chicago Midway

Thu 1/29

6:20 am-4:28 pm

1 stop9h 08m

$150

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 2/14

11:37 am-10:39 pm

1 stop12h 02m

Chicago O'Hare Intl

Wed 2/18

8:30 am-9:25 am

1 stop23h 55m

$152

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 2/2

5:33 pm-11:22 am

2 stops18h 49m

Chicago O'Hare Intl

Thu 2/5

6:57 pm-7:58 pm

1 stop24h 01m

$154

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $379. 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 $502.

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 $350. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $419.

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 $327 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 11% 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 January 2026, prices for Washington, D.C. Dulles Intl Airport to Chicago flights are approximately 23% 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

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

$246

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 $246. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago found on momondo in the last 72 hours is $358.
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

  • 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 $106Free CancellationRating
5.7
3,057 reviews
Search Frontier flights
United AirlinesPriceFrom $202Free CancellationRating
7.4
9,164 reviews
Search United Airlines flights
DeltaPriceFrom $234Free CancellationRating
7.9
8,051 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 14 times per week, with 9,163 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 $202 (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
Munster
Crown Point
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 2/14
Sat 2/21
By creating a price alert you accept our terms of use and privacy policy.

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