$95 Cheap Flights from Washington (IAD) to Chicago (ORD)

View $95 flight on Tue, Nov 3, 2026Opens in a new window

Popular airlines from Washington Dulles Intl. Airport (IAD) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Washington to Chicago (IAD-ORD)

Prices were available within the past 7 days and start at $95 for one-way flights and $190 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Jul 14 - Tue, Jul 21
IAD
Washington
ORD
Chicago
$190 Roundtrip, just found
$190
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jul 14 from Washington to Chicago, returning Tue, Jul 21, priced at $190 just found
United
Tue, Aug 11 - Wed, Aug 19
IAD
Washington
ORD
Chicago
$194 Roundtrip, found 2 hours ago
$194
Roundtrip
found 2 hours ago
Select United flight, departing Tue, Aug 11 from Washington to Chicago, returning Wed, Aug 19, priced at $194 found 2 hours ago
United
Tue, Jul 14 - Tue, Jul 21
IAD
Washington
ORD
Chicago
$197 Roundtrip, just found
$197
Roundtrip
just found
Select United flight, departing Tue, Jul 14 from Washington to Chicago, returning Tue, Jul 21, priced at $197 just found
Frontier Airlines
Tue, Aug 11 - Wed, Aug 19
IAD
Washington
ORD
Chicago
$199 Roundtrip, found 2 hours ago
$199
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Washington to Chicago, returning Wed, Aug 19, priced at $199 found 2 hours ago
Frontier Airlines
Tue, Aug 11 - Wed, Aug 19
IAD
Washington
ORD
Chicago
$200 Roundtrip, found 2 hours ago
$200
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Washington to Chicago, returning Wed, Aug 19, priced at $200 found 2 hours ago
Delta
Tue, Aug 11 - Wed, Aug 19
IAD
Washington
ORD
Chicago
$204 Roundtrip, found 2 hours ago
$204
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Aug 11 from Washington to Chicago, returning Wed, Aug 19, priced at $204 found 2 hours ago
Frontier Airlines
Tue, Aug 11 - Thu, Aug 20
IAD
Washington
ORD
Chicago
$204 Roundtrip, just found
$204
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Aug 11 from Washington to Chicago, returning Thu, Aug 20, priced at $204 just found
United
Tue, Aug 11 - Wed, Aug 19
IAD
Washington
ORD
Chicago
$206 Roundtrip, found 2 hours ago
$206
Roundtrip
found 2 hours ago
Select United flight, departing Tue, Aug 11 from Washington to Chicago, returning Wed, Aug 19, priced at $206 found 2 hours ago
American Airlines
Wed, Aug 12 - Sat, Aug 15
IAD
Washington
ORD
Chicago
$259 Roundtrip, found 2 hours ago
$259
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Aug 12 from Washington to Chicago, returning Sat, Aug 15, priced at $259 found 2 hours ago
Sun Country Airlines
Tue, Nov 24 - Mon, Nov 30
IAD
Washington
ORD
Chicago
$383 Roundtrip, found 9 hours ago
$383
Roundtrip
found 9 hours ago
Select Sun Country Airlines flight, departing Tue, Nov 24 from Washington to Chicago, returning Mon, Nov 30, priced at $383 found 9 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $270
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $270

Frequently asked questions

How much does a flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $95 and cheap return flights from $190 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $128 and $683, and return flights often range between $304 and $1193. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is typically the cheapest month to fly from Washington, DC (IAD) to Chicago, IL (ORD), with average round-trip fares around $288. This price is about 17% lower than the average throughout the year, as demand tends to decrease after the summer travel season. Other cheap months to fly from IAD to ORD include May and August.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
United operates around 46 direct flights from IAD to ORD every week.
What is the cheapest airline that flies from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Sun Country Airlines is one of the cheapest airlines offering connecting flights from Washington Dulles Intl. (IAD) to O'Hare Intl. (ORD), with round-trip tickets starting from around $370. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. United also offers the most daily flights from IAD to ORD, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
For flights from Washington, DC (IAD) to Chicago (ORD), September and August are the best months to fly, with average return flight prices around $288. These months are ideal as they offer lower prices after the summer peak, making it easier to find a good deal.*Prices based on flights available on Expedia in the last year.
How many flights per day from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
On average, there are around 7 nonstop flights per day from Washington Dulles Intl. (IAD) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Washington Dulles International (IAD) to O'Hare International (ORD) usually departs at around 5:00 AM, with American Airlines providing service. This seasonal route is available in February, perfect for those looking to start their day early in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Washington Dulles International Airport (IAD) to O'Hare International Airport (ORD) are in the early morning, from 6am to 9am. About 35% of passengers prefer this time window. Many major carriers, including United, Delta and American Airlines, offer flights during this window. This timing works well because it allows you to arrive in Chicago with a full day ahead of you.
How long does it take to fly from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from IAD to ORD typically takes around 2 hours 20 minutes, covering approximately 588 miles. Connecting flights on this route usually add 4 hours 40 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
First class seats are offered on the IAD to ORD route. First class cabins are available on:

  • American Airlines
  • United Airlines
  • Delta Air Lines

How much is a business class flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Washington, DC (IAD) to Chicago, IL (ORD) typically costs between $1,102 - $1,655. A non-stop, one-way business class flight is usually around $403 - $594 per adult. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Washington Dulles Intl. (IAD)?
From Washington Dulles Intl. (IAD), you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD) in Chicago. Some flights may connect through major hubs like Hopkins Intl. (CLE), Liberty Intl. (EWR), Denver Intl. (DEN) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Washington Dulles Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, Sun Country Airlines, United
Roundtrip price
$190
Distance
587 mi
Average flight time
1 hour 57 mins

Book with confidence

Washington to Chicago Flights

The cheapest times to fly from Washington to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Washington to Chicago are during the month of July. You can find some of the cheapest flights from Washington to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Washington to Chicago

Sunday is one of the best days to book for cheap flights from Washington to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Washington to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Washington to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $95 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Washington to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Washington to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Washington to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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