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

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash

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 $194 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
United
Frontier Airlines
Frontier Airlines
United
United
Delta
United
Southwest Airlines
American Airlines

Find the cheapest month to fly from Washington (IAD) to Chicago (ORD)

February is typically the cheapest month to fly

From $110 - $210 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Flights from Washington (IAD) to Chicago (ORD)
Origin airport
Washington Dulles Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, Southwest Airlines, United
Roundtrip price
$189
Distance
587 mi

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 September. 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 2025. 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.

 

Frequently asked questions

How much does a flight from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD) cost?
Grab a cheap one-way flight from $95 or cheap return flight from $194 from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from IAD to ORD is September, when demand is low. Off-peak months are typically when better flight deals are available between these airports.
Which airlines fly direct from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD)?
Hop on a direct flight with United Airlines and head straight from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest IAD to ORD flight.
How many flights per day from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD)?
When taking off from Washington Dulles Intl. Airport (IAD), you can choose from an average of 4 daily nonstop flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD)?
Flights between IAD and ORD are busiest at 1 PM. If you want a more relaxed atmosphere and potentially cheaper fares, look for a departure outside the usual busy windows.
What day of the week has the most flights from IAD to ORD?
Friday has the most flights from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD). Consider jetting off on this day and you'll have the best chance of finding a departure that fits your plans.
What is the earliest flight from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD)?
Washington Dulles Intl. Airport (IAD)'s first flight to O'Hare Intl. Airport (ORD) leaves at approximately 8:25AM UTC-5. With a travel time of 2h 19m, you'll land at around 9:44AM UTC-6.
How long does it take to fly from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD)?
Flights from IAD to ORD have an average travel time of 2 hours and 15 minutes. The distance between the two is 590 mi.
What is the best time to fly from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD)?
Select a flight from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the risk of cancellations and delays. Departures after this hour have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Washington Dulles Intl. Airport (IAD)?
If you're flying on a direct flight from Washington Dulles Intl. Airport (IAD) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD) last-minute?
Booking your ticket from IAD to ORD just before your getaway is typically more expensive. But if you're flexible with your departure times and dates, you could snag a cheap last-minute fare.
Is it cheaper to book an IAD to ORD flight and hotel package?
Securing an IAD to ORD flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Pick from our impressive 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 Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD)?
If you booked your IAD to ORD flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more information.

Explore a world of travel with Expedia

*Available to One Key members.