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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $90

1 adult
1 adult, Economy, 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.
Frontier Logo
8:05 am - 12:51 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
5h 46m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:15 am - 5:12 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
8h 57m1 stop Atlanta Hartsfield-Jackson
$181Frontier
Tue, Nov 3 - Sat, Nov 7
Frontier Logo
7:50 am - 6:31 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
11h 41m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:00 am - 5:13 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
10h 13m1 stop Atlanta Hartsfield-Jackson
$181Frontier
Wed, Oct 21 - Sat, Oct 24
Frontier Logo
8:05 am - 12:51 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
5h 46m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:15 am - 5:12 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
8h 57m1 stop Atlanta Hartsfield-Jackson
$181Frontier
Tue, Oct 27 - Sat, Oct 31
Frontier Logo
6:08 pm - 3:30 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
22h 22m1 stop Fort Lauderdale
Frontier Logo
8:04 am - 8:11 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
11h 07m1 stop Fort Lauderdale
$181Frontier
Tue, Oct 13 - Tue, Oct 20
Multiple Airlines Logo
6:36 pm - 7:51 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
14h 15m2 stops Blountville Tri Cities TN/VA Orlando
Multiple Airlines Logo
7:15 am - 5:12 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
8h 57m1 stop Atlanta Hartsfield-Jackson
$284Multiple Airlines
Fri, Oct 23 - Tue, Oct 27
Multiple Airlines Logo
2:15 pm - 6:43 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
5h 28m1 stop Minneapolis St Paul
Multiple Airlines Logo
8:11 pm - 10:21 amORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
13h 10m1 stop Orlando
$291Multiple Airlines
Thu, Oct 22 - Mon, Oct 26
United Airlines Logo
10:47 pm - 12:01 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 14mnonstop
United Airlines Logo
2:21 pm - 5:24 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 03mnonstop
$297United Airlines
Thu, Nov 5 - Tue, Nov 10
United Airlines Logo
10:10 am - 11:33 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 23mnonstop
United Airlines Logo
6:15 pm - 9:18 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 03mnonstop
$297United Airlines
Sat, Dec 5 - Sat, Dec 5
United Airlines Logo
1:00 pm - 2:23 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 23mnonstop
United Airlines Logo
9:35 pm - 12:24 amORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
1h 49mnonstop
$297United Airlines
Sat, Dec 5 - Mon, Dec 7
Delta Logo
12:20 pm - 4:26 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
5h 06m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:59 am - 11:26 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
12h 27m1 stop Minneapolis St Paul
$309Delta
Sat, Oct 24 - Tue, Oct 27

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

Our best Frontier deals on Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport flight tickets
Frontier
Oct 21
IAD7:50 amWashington, D.C. Dulles Intl
11h 41m
1 stop
ORD6:31 pmChicago O'Hare Intl
Oct 27
ORD7:15 amChicago O'Hare Intl
8h 57m
1 stop
IAD5:12 pmWashington, D.C. Dulles Intl
$181
Frontier
Oct 21
IAD7:50 amWashington, D.C. Dulles Intl
11h 41m
1 stop
ORD6:31 pmChicago O'Hare Intl
Oct 27
ORD7:15 amChicago O'Hare Intl
8h 57m
1 stop
IAD5:12 pmWashington, D.C. Dulles Intl
$183
Frontier
Oct 6
IAD6:13 pmWashington, D.C. Dulles Intl
22h 07m
1 stop
ORD3:20 pmChicago O'Hare Intl
Oct 28
ORD7:15 amChicago O'Hare Intl
8h 57m
1 stop
IAD5:12 pmWashington, D.C. Dulles Intl
$187

momondo Fare Finder

 
Use the filters below to find and compare flights from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Tue 11/3

8:05 am-12:51 pm

1 stop5h 46m

Chicago O'Hare Intl

Sat 11/7

7:15 am-5:12 pm

1 stop8h 57m

$181

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Wed 10/21

7:50 am-6:31 pm

1 stop11h 41m

Chicago O'Hare Intl

Sat 10/24

6:00 am-5:13 pm

1 stop10h 13m

$181

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Tue 10/27

8:05 am-12:51 pm

1 stop5h 46m

Chicago O'Hare Intl

Sat 10/31

7:15 am-5:12 pm

1 stop8h 57m

$181

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Tue 10/13

6:08 pm-3:30 pm

1 stop22h 22m

Chicago O'Hare Intl

Tue 10/20

8:04 am-8:11 pm

1 stop11h 07m

$181

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Fri 10/23

6:36 pm-7:51 am

2 stops14h 15m

Chicago O'Hare Intl

Tue 10/27

7:15 am-5:12 pm

1 stop8h 57m

$284

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Thu 10/22

2:15 pm-6:43 pm

1 stop5h 28m

Chicago O'Hare Intl

Mon 10/26

8:11 pm-10:21 am

1 stop13h 10m

$291

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Thu 11/5

10:47 pm-12:01 am

Nonstop2h 14m

Chicago O'Hare Intl

Tue 11/10

2:21 pm-5:24 pm

Nonstop2h 03m

$297

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Sat 12/5

10:10 am-11:33 am

Nonstop2h 23m

Chicago O'Hare Intl

Sat 12/5

6:15 pm-9:18 pm

Nonstop2h 03m

$297
Quickest round-trip

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Sat 12/5

1:00 pm-2:23 pm

Nonstop2h 23m

Chicago O'Hare Intl

Mon 12/7

9:35 pm-12:24 am

Nonstop1h 49m

$297

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Sat 10/24

12:20 pm-4:26 pm

1 stop5h 06m

Chicago O'Hare Intl

Tue 10/27

9:59 am-11:26 pm

1 stop12h 27m

$309

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 O'Hare Intl Airport

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 O'Hare Intl Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $254 to $400.
The lowest price recently found on this route was $181.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Washington, D.C. Dulles Intl Airport averaging around $339.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $418. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Washington, D.C. Dulles Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $552.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Washington, D.C. Dulles Intl Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $443 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $485. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

How far in advance should I book a flight from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport for around $404 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Washington, D.C. Dulles Intl Airport for as low as $302 on momondo.

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

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

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

As of September 2026, prices for Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport flights are approximately 0% 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 O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (IAD to ORD) 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 O'Hare Intl Airport

Best Price Found

$90

Fastest flight time

2h 04m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Washington, D.C. Dulles Intl Airport in the past 72 hours is $90. The best round-trip flight deal from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $181.
The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport takes 2h 04m
Direct flights go from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport every day.
Search flight deals

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

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

    The straight-line distance from Washington, D.C. Dulles Intl to Chicago O'Hare Intl is 587.2 mi. By plane, this route typically takes 2h 04m.

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

    Prices for flights from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

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

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago O'Hare Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

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

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

Compare and see reviews for airlines that fly from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $90Free CancellationRating
5.6
2,578 reviews
Search Frontier flights
United AirlinesPriceFrom $211Free CancellationRating
7.4
10,234 reviews
Search United Airlines flights

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

    Across 13 United Airlines flights from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport this week, the average price was $402, with the best United Airlines deals starting from $211 round-trip. 10,233 users have rated United Airlines on momondo, with an average score of 7.4/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
Merrillville
Rockford
South Haven
Rosemont
Gurnee
Oak Brook
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Evanston
Skokie

Why use momondo?

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

It is quick and easy to find Washington, D.C. to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Washington, D.C. to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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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