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Cheap flights from Washington, D.C. Dulles Intl Airport to Chicago from $89

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 8/24. 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

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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
11:12 am - 10:59 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
12h 47m1 stop Orlando
Frontier Logo
10:26 am - 5:18 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
5h 52m1 stop Atlanta Hartsfield-Jackson
$190Frontier
Thu, Sep 17 - Mon, Sep 21
Frontier Logo
6:09 pm - 12:50 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
19h 41m1 stop Fort Lauderdale
Frontier Logo
1:59 pm - 10:52 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
7h 53m1 stop Atlanta Hartsfield-Jackson
$190Frontier
Tue, Aug 25 - Sat, Aug 29
Frontier Logo
8:39 pm - 7:53 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
12h 14m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
9:20 am - 6:29 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
8h 09m1 stop Dallas/Fort Worth
$190Frontier
Tue, Aug 25 - Thu, Aug 27
Frontier Logo
11:12 am - 10:59 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
12h 47m1 stop Orlando
Frontier Logo
10:26 am - 5:18 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
5h 52m1 stop Atlanta Hartsfield-Jackson
$191Frontier
Thu, Sep 17 - Mon, Sep 21
Delta Logo
6:00 am - 12:40 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
7h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:10 pm - 11:14 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
5h 04m1 stop Detroit Metropolitan Wayne County
$197Delta
Sun, Sep 6 - Fri, Sep 11
Delta Logo
12:29 pm - 5:06 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
5h 37m1 stop New York John F Kennedy Intl
Delta Logo
6:25 pm - 12:41 amORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
5h 16m1 stop Atlanta Hartsfield-Jackson
$197Delta
Sun, Sep 6 - Fri, Sep 11
Delta Logo
5:25 pm - 8:30 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
4h 05m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:10 pm - 11:14 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
5h 04m1 stop Detroit Metropolitan Wayne County
$197Delta
Sat, Sep 5 - Fri, Sep 11
United Airlines Logo
10:35 am - 11:53 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 18mnonstop
United Airlines Logo
6:15 pm - 9:20 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 05mnonstop
$216United Airlines
Sat, Aug 29 - Sat, Sep 5
United Airlines Logo
6:11 am - 7:30 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 19mnonstop
United Airlines Logo
11:15 am - 2:03 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
1h 48mnonstop
$216United Airlines
Thu, Nov 26 - Tue, Dec 1
United Airlines Logo
1:13 pm - 2:30 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 17mnonstop
United Airlines Logo
10:50 am - 1:55 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 05mnonstop
$216United Airlines
Tue, Aug 25 - Sun, Sep 6

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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
Aug 25
IAD8:39 pmWashington, D.C. Dulles Intl
12h 14m
1 stop
ORD7:53 amChicago O'Hare Intl
Aug 27
ORD9:20 amChicago O'Hare Intl
8h 09m
1 stop
IAD6:29 pmWashington, D.C. Dulles Intl
$190
Frontier
Sep 17
IAD11:12 amWashington, D.C. Dulles Intl
12h 47m
1 stop
ORD10:59 pmChicago O'Hare Intl
Sep 21
ORD10:26 amChicago O'Hare Intl
5h 52m
1 stop
IAD5:18 pmWashington, D.C. Dulles Intl
$191
Frontier
Aug 19
IAD6:20 amWashington, D.C. Dulles Intl
14h 48m
1 stop
ORD8:08 pmChicago O'Hare Intl
Aug 25
ORD9:20 amChicago O'Hare Intl
8h 09m
1 stop
IAD6:29 pmWashington, D.C. Dulles Intl
$193

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
Sep 6
IAD6:00 amWashington, D.C. Dulles Intl
7h 40m
1 stop
ORD12:40 pmChicago O'Hare Intl
Sep 11
ORD5:10 pmChicago O'Hare Intl
5h 04m
1 stop
IAD11:14 pmWashington, D.C. Dulles Intl
$197
Delta
Sep 11
IAD6:07 pmWashington, D.C. Dulles Intl
6h 52m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 14
ORD5:10 pmChicago O'Hare Intl
5h 04m
1 stop
IAD11:14 pmWashington, D.C. Dulles Intl
$236

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 August 6, 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 Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Thu 9/17

11:12 am-10:59 pm

1 stop12h 47m

Chicago O'Hare Intl

Mon 9/21

10:26 am-5:18 pm

1 stop5h 52m

$190

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Tue 8/25

6:09 pm-12:50 pm

1 stop19h 41m

Chicago O'Hare Intl

Sat 8/29

1:59 pm-10:52 pm

1 stop7h 53m

$190

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Tue 8/25

8:39 pm-7:53 am

1 stop12h 14m

Chicago O'Hare Intl

Thu 8/27

9:20 am-6:29 pm

1 stop8h 09m

$190

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Thu 9/17

11:12 am-10:59 pm

1 stop12h 47m

Chicago O'Hare Intl

Mon 9/21

10:26 am-5:18 pm

1 stop5h 52m

$191

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Sun 9/6

6:00 am-12:40 pm

1 stop7h 40m

Chicago O'Hare Intl

Fri 9/11

5:10 pm-11:14 pm

1 stop5h 04m

$197

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Sun 9/6

12:29 pm-5:06 pm

1 stop5h 37m

Chicago O'Hare Intl

Fri 9/11

6:25 pm-12:41 am

1 stop5h 16m

$197

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Sat 9/5

5:25 pm-8:30 pm

1 stop4h 05m

Chicago O'Hare Intl

Fri 9/11

5:10 pm-11:14 pm

1 stop5h 04m

$197

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Sat 8/29

10:35 am-11:53 am

Nonstop2h 18m

Chicago O'Hare Intl

Sat 9/5

6:15 pm-9:20 pm

Nonstop2h 05m

$216
Quickest round-trip

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Thu 11/26

6:11 am-7:30 am

Nonstop2h 19m

Chicago O'Hare Intl

Tue 12/1

11:15 am-2:03 pm

Nonstop1h 48m

$216

Washington, D.C.Chicago

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

IADORD

Washington, D.C. Dulles Intl

Tue 8/25

1:13 pm-2:30 pm

Nonstop2h 17m

Chicago O'Hare Intl

Sun 9/6

10:50 am-1:55 pm

Nonstop2h 05m

$216

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?

Prices are currently low for flights on this route.

Typical prices usually range from $244 to $419.
The lowest price recently found on this route was $190.

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 $336.

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 $410. 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 $562.

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 $426 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $480. 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 $398 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 $284 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 18% 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 August 2026, prices for Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport flights are approximately 2% 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

$236

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 $236. 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 $363.
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
2,723 reviews
Search Frontier flights
United AirlinesPriceFrom $220Free CancellationRating
7.4
10,072 reviews
Search United Airlines flights

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

    Across 42 United Airlines flights from Washington, D.C. Dulles Intl Airport to Chicago O'Hare Intl Airport this week, the average price was $400, with the best United Airlines deals starting from $220 round-trip. 10,072 users have rated United Airlines on momondo, with an average score of 7.4/10.

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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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