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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 7/14. 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
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
9:50 am - 5:37 am
IAD
-
ORD
20h 47m
1 stop
Frontier Logo
1:50 pm - 10:55 pm
ORD
-
IAD
8h 05m
1 stop
$247Frontier
Tue, Jul 28 - Wed, Jul 29
Frontier Logo
8:57 pm - 8:03 am
IAD
-
ORD
12h 06m
1 stop
Frontier Logo
8:05 am - 7:38 pm
ORD
-
IAD
10h 33m
1 stop
$248Frontier
Tue, Jun 30 - Tue, Jul 7
Frontier Logo
8:33 pm - 7:53 am
IAD
-
ORD
12h 20m
1 stop
Frontier Logo
8:05 am - 7:38 pm
ORD
-
IAD
10h 33m
1 stop
$249Frontier
Mon, Jul 13 - Wed, Jul 15
Frontier Logo
8:33 pm - 7:53 am
IAD
-
ORD
12h 20m
1 stop
Frontier Logo
7:05 am - 4:40 pm
ORD
-
IAD
8h 35m
1 stop
$250Frontier
Fri, Jul 10 - Tue, Jul 21
Frontier Logo
7:48 am - 7:53 pm
IAD
-
ORD
13h 05m
1 stop
Frontier Logo
8:05 am - 7:38 pm
ORD
-
IAD
10h 33m
1 stop
$252Frontier
Thu, Aug 6 - Mon, Aug 10
United Airlines Logo
8:20 am - 9:38 am
IAD
-
ORD
2h 18mnonstop
United Airlines Logo
6:30 am - 9:28 am
ORD
-
IAD
1h 58mnonstop
$253United Airlines
Tue, Aug 18 - Wed, Aug 19
Frontier Logo
4:52 pm - 11:08 pm
IAD
-
ORD
7h 16m
1 stop
Frontier Logo
8:05 am - 7:44 pm
ORD
-
IAD
10h 39m
1 stop
$254Frontier
Sun, Aug 23 - Sat, Aug 29
Frontier Logo
7:48 am - 7:53 pm
IAD
-
ORD
13h 05m
1 stop
Frontier Logo
8:05 am - 7:38 pm
ORD
-
IAD
10h 33m
1 stop
$255Frontier
Thu, Aug 6 - Mon, Aug 10
Frontier Logo
8:33 pm - 8:02 am
IAD
-
ORD
12h 29m
1 stop
Frontier Logo
7:05 am - 5:14 pm
ORD
-
IAD
9h 09m
1 stop
$256Frontier
Sat, Aug 8 - Mon, Aug 10
United Airlines Logo
3:39 pm - 5:02 pm
IAD
-
ORD
2h 23mnonstop
United Airlines Logo
1:30 pm - 4:30 pm
ORD
-
IAD
2h 00mnonstop
$257United Airlines
Tue, Jul 14 - Tue, Jul 21

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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
Jul 28
IAD9:50 amWashington, D.C. Dulles Intl
20h 47m
1 stop
ORD5:37 amChicago O'Hare Intl
Jul 29
ORD1:50 pmChicago O'Hare Intl
8h 05m
1 stop
IAD10:55 pmWashington, D.C. Dulles Intl
$247
Frontier
Jun 30
IAD8:57 pmWashington, D.C. Dulles Intl
12h 06m
1 stop
ORD8:03 amChicago O'Hare Intl
Jul 7
ORD8:05 amChicago O'Hare Intl
10h 33m
1 stop
IAD7:38 pmWashington, D.C. Dulles Intl
$248
Frontier
Jul 13
IAD8:33 pmWashington, D.C. Dulles Intl
12h 20m
1 stop
ORD7:53 amChicago O'Hare Intl
Jul 15
ORD8:05 amChicago O'Hare Intl
10h 33m
1 stop
IAD7:38 pmWashington, D.C. Dulles Intl
$249

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
Aug 18
IAD8:20 amWashington, D.C. Dulles Intl
2h 18m
ORD9:38 amChicago O'Hare Intl
Aug 19
ORD6:30 amChicago O'Hare Intl
1h 58m
IAD9:28 amWashington, D.C. Dulles Intl
$253
United Airlines
Aug 1
IAD10:20 pmWashington, D.C. Dulles Intl
2h 11m
ORD11:31 pmChicago O'Hare Intl
Aug 3
ORD9:40 pmChicago O'Hare Intl
2h 05m
IAD12:45 amWashington, D.C. Dulles Intl
$254
United Airlines
Jul 14
IAD3:39 pmWashington, D.C. Dulles Intl
2h 23m
ORD5:02 pmChicago O'Hare Intl
Jul 21
ORD1:30 pmChicago O'Hare Intl
2h 00m
IAD4:30 pmWashington, D.C. Dulles Intl
$257

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 June 21, 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

Tue 7/28

9:50 am-5:37 am

1 stop20h 47m

Chicago O'Hare Intl

Wed 7/29

1:50 pm-10:55 pm

1 stop8h 05m

$247

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 6/30

8:57 pm-8:03 am

1 stop12h 06m

Chicago O'Hare Intl

Tue 7/7

8:05 am-7:38 pm

1 stop10h 33m

$248

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 7/13

8:33 pm-7:53 am

1 stop12h 20m

Chicago O'Hare Intl

Wed 7/15

8:05 am-7:38 pm

1 stop10h 33m

$249

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 7/10

8:33 pm-7:53 am

1 stop12h 20m

Chicago O'Hare Intl

Tue 7/21

7:05 am-4:40 pm

1 stop8h 35m

$250

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 8/6

7:48 am-7:53 pm

1 stop13h 05m

Chicago O'Hare Intl

Mon 8/10

8:05 am-7:38 pm

1 stop10h 33m

$252
Quickest round-trip

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 8/18

8:20 am-9:38 am

Nonstop2h 18m

Chicago O'Hare Intl

Wed 8/19

6:30 am-9:28 am

Nonstop1h 58m

$253

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 8/23

4:52 pm-11:08 pm

1 stop7h 16m

Chicago O'Hare Intl

Sat 8/29

8:05 am-7:44 pm

1 stop10h 39m

$254

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 8/6

7:48 am-7:53 pm

1 stop13h 05m

Chicago O'Hare Intl

Mon 8/10

8:05 am-7:38 pm

1 stop10h 33m

$255

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sat 8/8

8:33 pm-8:02 am

1 stop12h 29m

Chicago O'Hare Intl

Mon 8/10

7:05 am-5:14 pm

1 stop9h 09m

$256

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 7/14

3:39 pm-5:02 pm

Nonstop2h 23m

Chicago O'Hare Intl

Tue 7/21

1:30 pm-4:30 pm

Nonstop2h 00m

$257

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $303.

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 $406. 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 $560.

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 $415 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $459. 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 $382 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 $232 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.

Can stopping save me money on Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport flights?

You could potentially save up to 24% on your flight if you consider stops on a Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport flight.

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

As of June 2026, prices for Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport flights are approximately 18% 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

$250

Fastest flight time

2h 03m

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 $250. 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 $358.
The fastest flight from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport takes 2h 03m
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 03m.

  • 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
2,875 reviews
Search Frontier flights
United AirlinesPriceFrom $227Free CancellationRating
7.4
9,870 reviews
Search United Airlines flights

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

    Across 29 United Airlines flights from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport this week, the average price was $388, with the best United Airlines deals starting from $227 round-trip. 9,870 users have rated United Airlines on momondo, with an average score of 7.4/10.

Traveling to a place near Chicago?

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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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