$81 Cheap Flights from Washington (IAD) to Chicago (ORD)

View $81 flight on Sat, Aug 30, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Washington to Chicago (IAD-ORD)

Prices were available within the past 7 days and start at $81 for one-way flights and $166 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, May 16 - Sat, May 24
IAD
Washington
ORD
Chicago
$166 Roundtrip, found 1 hour ago
$166
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, May 16 from Washington to Chicago, returning Sat, May 24, priced at $166 found 1 hour ago
United
Sat, May 24 - Sat, May 31
IAD
Washington
ORD
Chicago
$170 Roundtrip, found 3 hours ago
$170
Roundtrip
found 3 hours ago
Select United flight, departing Sat, May 24 from Washington to Chicago, returning Sat, May 31, priced at $170 found 3 hours ago
Frontier Airlines
Mon, May 19 - Sun, May 25
IAD
Washington
ORD
Chicago
$172 Roundtrip, found 6 hours ago
$172
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, May 19 from Washington to Chicago, returning Sun, May 25, priced at $172 found 6 hours ago
Frontier Airlines
Wed, May 21 - Thu, May 29
IAD
Washington
ORD
Chicago
$175 Roundtrip, found 1 hour ago
$175
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, May 21 from Washington to Chicago, returning Thu, May 29, priced at $175 found 1 hour ago
United
Tue, Jul 1 - Fri, Jul 4
IAD
Washington
ORD
Chicago
$178 Roundtrip, found 12 hours ago
$178
Roundtrip
found 12 hours ago
Select United flight, departing Tue, Jul 1 from Washington to Chicago, returning Fri, Jul 4, priced at $178 found 12 hours ago
United
Tue, Jul 1 - Fri, Jul 4
IAD
Washington
ORD
Chicago
$179 Roundtrip, found 12 hours ago
$179
Roundtrip
found 12 hours ago
Select United flight, departing Tue, Jul 1 from Washington to Chicago, returning Fri, Jul 4, priced at $179 found 12 hours ago
United
Thu, May 29 - Sat, May 31
IAD
Washington
ORD
Chicago
$179 Roundtrip, found 6 hours ago
$179
Roundtrip
found 6 hours ago
Select United flight, departing Thu, May 29 from Washington to Chicago, returning Sat, May 31, priced at $179 found 6 hours ago
Delta
Tue, Jul 1 - Fri, Jul 4
IAD
Washington
ORD
Chicago
$182 Roundtrip, found 12 hours ago
$182
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Jul 1 from Washington to Chicago, returning Fri, Jul 4, priced at $182 found 12 hours ago
American Airlines
Tue, Jun 3 - Wed, Jun 11
IAD
Washington
ORD
Chicago
$251 Roundtrip, found 1 hour ago
$251
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jun 3 from Washington to Chicago, returning Wed, Jun 11, priced at $251 found 1 hour ago
Southwest Airlines
Mon, Jul 14 - Wed, Jul 16
IAD
Washington
ORD
Chicago
$265 Roundtrip, found 14 hours ago
$265
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Mon, Jul 14 from Washington to Chicago, returning Wed, Jul 16, priced at $265 found 14 hours ago

Frequently asked questions

How much does a flight from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD) cost?
You can score cheap return tickets from Washington Dulles Intl. Airport (IAD) to O’Hare Intl. Airport (ORD) starting at $131. Grab a seat and set off on your next adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United and Spirit Airlines flight leaving IAD on May 11 2025 and touching down at ORD. The price was last updated on April 22 2025 and has not changed since.
What is the cheapest month to fly from IAD to ORD?
The cheapest flights from IAD to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 IAD to ORD?
Journey from IAD to ORD with United. This carrier currently has the lowest one-way fare on this route, starting at $81. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from IAD on July 4 2025. Prices were last updated on April 22 2025 and have not changed since.
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.
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