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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $99

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 6/16. 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

Enter your travel dates to find the best prices.
Frontier Logo
11:17 am - 7:50 pm
IAD
-
ORD
9h 33m
1 stop
Frontier Logo
1:50 pm - 11:13 pm
ORD
-
IAD
8h 23m
1 stop
$224Frontier
Wed, Jul 1 - Sat, Aug 15
Frontier Logo
11:07 am - 7:41 pm
IAD
-
ORD
9h 34m
1 stop
Frontier Logo
6:55 am - 5:27 pm
ORD
-
IAD
9h 32m
1 stop
$225Frontier
Fri, May 29 - Wed, Jun 3
Frontier Logo
6:22 pm - 12:37 pm
IAD
-
ORD
19h 15m
1 stop
Frontier Logo
9:37 pm - 4:22 pm
ORD
-
IAD
17h 45m
2 stops
$226Frontier
Wed, May 27 - Tue, Jun 2
Delta Logo
6:00 am - 8:45 am
IAD
-
ORD
3h 45m
1 stop
Delta Logo
12:00 pm - 8:02 pm
ORD
-
IAD
7h 02m
1 stop
$228Delta
Tue, May 26 - Sat, May 30
Frontier Logo
8:57 pm - 7:53 am
IAD
-
ORD
11h 56m
1 stop
Frontier Logo
1:50 pm - 11:13 pm
ORD
-
IAD
8h 23m
1 stop
$230Frontier
Fri, Jul 10 - Sun, Jul 12
Frontier Logo
11:12 am - 7:51 pm
IAD
-
ORD
9h 39m
1 stop
Frontier Logo
6:55 am - 4:52 pm
ORD
-
IAD
8h 57m
1 stop
$231Frontier
Wed, May 20 - Thu, Jun 11
Frontier Logo
11:07 am - 7:29 pm
IAD
-
ORD
9h 22m
1 stop
Frontier Logo
9:48 pm - 4:00 pm
ORD
-
IAD
17h 12m
2 stops
$232Frontier
Wed, Jun 3 - Fri, Jun 12
United Airlines Logo
10:15 pm - 11:26 pm
IAD
-
ORD
2h 11mnonstop
United Airlines Logo
3:53 pm - 7:02 pm
ORD
-
IAD
2h 09mnonstop
$233United Airlines
Sat, Jun 13 - Tue, Jun 16
Frontier Logo
8:47 pm - 7:55 am
IAD
-
ORD
12h 08m
1 stop
Frontier Logo
6:55 am - 4:21 pm
ORD
-
IAD
8h 26m
1 stop
$234Frontier
Sat, May 23 - Thu, May 28
Frontier Logo
12:56 pm - 7:41 pm
IAD
-
ORD
7h 45m
1 stop
Frontier Logo
6:55 am - 4:20 pm
ORD
-
IAD
8h 25m
1 stop
$235Frontier
Thu, May 21 - Tue, Jun 9

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

Our best United Airlines deals on Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport flight tickets
United Airlines
Jun 13
IAD10:15 pmWashington, D.C. Dulles Intl
2h 11m
ORD11:26 pmChicago O'Hare Intl
Jun 16
ORD3:53 pmChicago O'Hare Intl
2h 09m
IAD7:02 pmWashington, D.C. Dulles Intl
$233
United Airlines
May 28
IAD6:10 amWashington, D.C. Dulles Intl
2h 17m
ORD7:27 amChicago O'Hare Intl
May 30
ORD9:55 pmChicago O'Hare Intl
2h 04m
IAD12:59 amWashington, D.C. Dulles Intl
$239
United Airlines
Jun 9
IAD8:15 amWashington, D.C. Dulles Intl
2h 21m
ORD9:36 amChicago O'Hare Intl
Jun 13
ORD3:53 pmChicago O'Hare Intl
2h 09m
IAD7:02 pmWashington, D.C. Dulles Intl
$243

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

Our best Delta deals on Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport flight tickets
Delta
May 26
IAD6:00 amWashington, D.C. Dulles Intl
3h 45m
1 stop
ORD8:45 amChicago O'Hare Intl
May 30
ORD12:00 pmChicago O'Hare Intl
7h 02m
1 stop
IAD8:02 pmWashington, D.C. Dulles Intl
$228
Delta
May 27
IAD6:00 amWashington, D.C. Dulles Intl
3h 45m
1 stop
ORD8:45 amChicago O'Hare Intl
May 30
ORD5:19 pmChicago O'Hare Intl
4h 37m
1 stop
IAD10:56 pmWashington, D.C. Dulles Intl
$238
Delta
May 27
IAD5:33 pmWashington, D.C. Dulles Intl
7h 26m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 30
ORD3:47 pmChicago O'Hare Intl
6h 52m
1 stop
IAD11:39 pmWashington, D.C. Dulles Intl
$248

momondo Fare Finder

 
Customize your flight search to find flights from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport 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 May 7, 2026.
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 - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 7/1

11:17 am-7:50 pm

1 stop9h 33m

Chicago O'Hare Intl

Sat 8/15

1:50 pm-11:13 pm

1 stop8h 23m

$224

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 5/29

11:07 am-7:41 pm

1 stop9h 34m

Chicago O'Hare Intl

Wed 6/3

6:55 am-5:27 pm

1 stop9h 32m

$225

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 5/27

6:22 pm-12:37 pm

1 stop19h 15m

Chicago O'Hare Intl

Tue 6/2

9:37 pm-4:22 pm

2 stops17h 45m

$226

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 5/26

6:00 am-8:45 am

1 stop3h 45m

Chicago O'Hare Intl

Sat 5/30

12:00 pm-8:02 pm

1 stop7h 02m

$228

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 7/10

8:57 pm-7:53 am

1 stop11h 56m

Chicago O'Hare Intl

Sun 7/12

1:50 pm-11:13 pm

1 stop8h 23m

$230

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 5/20

11:12 am-7:51 pm

1 stop9h 39m

Chicago O'Hare Intl

Thu 6/11

6:55 am-4:52 pm

1 stop8h 57m

$231

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 6/3

11:07 am-7:29 pm

1 stop9h 22m

Chicago O'Hare Intl

Fri 6/12

9:48 pm-4:00 pm

2 stops17h 12m

$232
Quickest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 6/13

10:15 pm-11:26 pm

Nonstop2h 11m

Chicago O'Hare Intl

Tue 6/16

3:53 pm-7:02 pm

Nonstop2h 09m

$233

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 5/23

8:47 pm-7:55 am

1 stop12h 08m

Chicago O'Hare Intl

Thu 5/28

6:55 am-4:21 pm

1 stop8h 26m

$234

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 5/21

12:56 pm-7:41 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 6/9

6:55 am-4:20 pm

1 stop8h 25m

$235

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 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?

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

The month of August 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 $296.

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 Friday when prices can be found for as low as $398. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $533.

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 $391 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $441. 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 $374 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 $201 on momondo.

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

As of May 2026, prices for Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport flights are approximately 15% cheaper 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

$253

Fastest flight time

2h 05m

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 $253. 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 $359.
The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport takes 2h 05m
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 05m.

  • 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
2,962 reviews
Search Frontier flights
United AirlinesPriceFrom $207Free CancellationRating
7.4
9,692 reviews
Search United Airlines flights

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

    Across 56 United Airlines flights from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport this week, the average price was $373, with the best United Airlines deals starting from $207 round-trip. 9,692 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
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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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