S$152 Cheap Flights from Washington to Chicago

View S$152 flight on Wed, 8 Oct, 2025Opens 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 S$152 for one-way flights and S$369 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Thu, 18 Sep - Mon, 22 Sep
IAD
Washington
ORD
Chicago
S$369 Return, found 3 days ago
S$369
Return
found 3 days ago
Select United flight, departing Thu, 18 Sep from Washington to Chicago, returning Mon, 22 Sep, priced at S$369 found 3 days ago
United
Thu, 18 Sep - Mon, 22 Sep
IAD
Washington
ORD
Chicago
S$370 Return, found 3 days ago
S$370
Return
found 3 days ago
Select United flight, departing Thu, 18 Sep from Washington to Chicago, returning Mon, 22 Sep, priced at S$370 found 3 days ago
United
Thu, 18 Sep - Mon, 22 Sep
IAD
Washington
ORD
Chicago
S$411 Return, found 3 days ago
S$411
Return
found 3 days ago
Select United flight, departing Thu, 18 Sep from Washington to Chicago, returning Mon, 22 Sep, priced at S$411 found 3 days ago
United
Thu, 18 Sep - Mon, 22 Sep
IAD
Washington
ORD
Chicago
S$454 Return, found 3 days ago
S$454
Return
found 3 days ago
Select United flight, departing Thu, 18 Sep from Washington to Chicago, returning Mon, 22 Sep, priced at S$454 found 3 days ago
United
Thu, 18 Sep - Mon, 22 Sep
IAD
Washington
ORD
Chicago
S$456 Return, found 3 days ago
S$456
Return
found 3 days ago
Select United flight, departing Thu, 18 Sep from Washington to Chicago, returning Mon, 22 Sep, priced at S$456 found 3 days ago
United
Thu, 18 Sep - Mon, 22 Sep
IAD
Washington
ORD
Chicago
S$478 Return, found 3 days ago
S$478
Return
found 3 days ago
Select United flight, departing Thu, 18 Sep from Washington to Chicago, returning Mon, 22 Sep, priced at S$478 found 3 days ago
United
Thu, 18 Sep - Mon, 22 Sep
IAD
Washington
ORD
Chicago
S$496 Return, found 3 days ago
S$496
Return
found 3 days ago
Select United flight, departing Thu, 18 Sep from Washington to Chicago, returning Mon, 22 Sep, priced at S$496 found 3 days ago
United
Thu, 18 Sep - Mon, 22 Sep
IAD
Washington
ORD
Chicago
S$517 Return, found 3 days ago
S$517
Return
found 3 days ago
Select United flight, departing Thu, 18 Sep from Washington to Chicago, returning Mon, 22 Sep, priced at S$517 found 3 days ago
United
Thu, 18 Sep - Mon, 22 Sep
IAD
Washington
ORD
Chicago
S$525 Return, found 3 days ago
S$525
Return
found 3 days ago
Select United flight, departing Thu, 18 Sep from Washington to Chicago, returning Mon, 22 Sep, priced at S$525 found 3 days ago
United
Thu, 18 Sep - Mon, 22 Sep
IAD
Washington
ORD
Chicago
S$544 Return, found 3 days ago
S$544
Return
found 3 days ago
Select United flight, departing Thu, 18 Sep from Washington to Chicago, returning Mon, 22 Sep, priced at S$544 found 3 days ago

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

February is typically the cheapest month to fly

From S$141 - S$330 per traveller.

Graph displaying average flight prices per month

Washington to Chicago route information
Origin airport
Washington Dulles Intl.
Destination airport
O'Hare Intl.
Return price
S$368
Distance
940 km
Average flight time
1 hour 12 mins

Perfect flights from Washington to Chicago

Your Journey from Washington to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Washington to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, United, American Airlines. Our selection of flights from Washington Dulles Intl. to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Washington to Chicago Flights

Experience the joy of finding cheap flights from Washington Dulles Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$152 and roundtrip prices from S$369*.
 

Pre-Flight Essentials

Ensure a smooth journey from Washington to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of Chicago. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Washington to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Washington to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Washington to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Washington to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from Dulles Intl. Airport to O'Hare Airport?
Round-trip flights from Washington Dulles Intl. Airport (IAD) to ORD start from S$369. This is based on fares advertised within the last 7 days on Expedia for flights departing within the next year — book ASAP so you don't miss out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Washington Dulles Intl. Airport (IAD) to O'Hare Airport?
Each air carrier has its own terms and conditions. If you do decide to cancel, follow the instructions on our Customer Service Portal.
How do I find cheap flights from IAD to ORD that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Dulles Intl. Airport to O'Hare Intl. Airport (ORD) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Washington Dulles Intl. Airport (IAD) to O'Hare Intl. Airport (ORD)?
With a flight distance of 950 kilometres, it's just a hop from IAD to O'Hare Airport. It might be a quick journey, but it's still worth bringing something to read.
Which airlines fly direct from IAD to O'Hare Airport?
Offering 152 monthly flights, United Airlines (UA) is a great choice when flying straight from Washington Dulles Intl. Airport (IAD) to ORD.
Are Dulles Intl. Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Flight prices go up and down like a yo-yo, so there are no guarantees. While last-minute flight deals between Washington Dulles Intl. Airport (IAD) and O'Hare Intl. Airport (ORD) are possible, it also makes sense to keep track of prices well before you fly. In fact, some air carriers publicize their prices up to a year ahead of the departure date. Expedia is constantly updating the best bargains around, so keep checking and be ready to lock in your seat when the price is low.

Explore a world of travel with Expedia

*Available to Expedia members.