S$121 Cheap Flights from Washington to Chicago

View S$121 flight on Fri, 22 Aug, 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$121 for one-way flights and S$242 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, 22 Aug - Fri, 29 Aug
IAD
Washington
ORD
Chicago
S$242 Return, found 13 hours ago
S$242
Return
found 13 hours ago
Select United flight, departing Fri, 22 Aug from Washington to Chicago, returning Fri, 29 Aug, priced at S$242 found 13 hours ago
Delta
Fri, 22 Aug - Fri, 29 Aug
IAD
Washington
ORD
Chicago
S$247 Return, found 13 hours ago
S$247
Return
found 13 hours ago
Select Delta flight, departing Fri, 22 Aug from Washington to Chicago, returning Fri, 29 Aug, priced at S$247 found 13 hours ago
United
Fri, 22 Aug - Fri, 29 Aug
IAD
Washington
ORD
Chicago
S$267 Return, found 13 hours ago
S$267
Return
found 13 hours ago
Select United flight, departing Fri, 22 Aug from Washington to Chicago, returning Fri, 29 Aug, priced at S$267 found 13 hours ago
United
Wed, 20 Aug - Wed, 27 Aug
IAD
Washington
ORD
Chicago
S$272 Return, found 2 days ago
S$272
Return
found 2 days ago
Select United flight, departing Wed, 20 Aug from Washington to Chicago, returning Wed, 27 Aug, priced at S$272 found 2 days ago
Delta
Sat, 16 Aug - Mon, 18 Aug
IAD
Washington
ORD
Chicago
S$275 Return, found 2 days ago
S$275
Return
found 2 days ago
Select Delta flight, departing Sat, 16 Aug from Washington to Chicago, returning Mon, 18 Aug, priced at S$275 found 2 days ago
Delta
Fri, 22 Aug - Fri, 29 Aug
IAD
Washington
ORD
Chicago
S$287 Return, found 13 hours ago
S$287
Return
found 13 hours ago
Select Delta flight, departing Fri, 22 Aug from Washington to Chicago, returning Fri, 29 Aug, priced at S$287 found 13 hours ago
United
Sat, 16 Aug - Sat, 23 Aug
IAD
Washington
ORD
Chicago
S$289 Return, found 6 days ago
S$289
Return
found 6 days ago
Select United flight, departing Sat, 16 Aug from Washington to Chicago, returning Sat, 23 Aug, priced at S$289 found 6 days ago
United
Wed, 20 Aug - Wed, 27 Aug
IAD
Washington
ORD
Chicago
S$290 Return, found 2 days ago
S$290
Return
found 2 days ago
Select United flight, departing Wed, 20 Aug from Washington to Chicago, returning Wed, 27 Aug, priced at S$290 found 2 days ago
United
Sat, 16 Aug - Mon, 18 Aug
IAD
Washington
ORD
Chicago
S$305 Return, found 2 days ago
S$305
Return
found 2 days ago
Select United flight, departing Sat, 16 Aug from Washington to Chicago, returning Mon, 18 Aug, priced at S$305 found 2 days ago
American Airlines
Sat, 16 Aug - Mon, 18 Aug
IAD
Washington
ORD
Chicago
S$351 Return, found 2 days ago
S$351
Return
found 2 days ago
Select American Airlines flight, departing Sat, 16 Aug from Washington to Chicago, returning Mon, 18 Aug, priced at S$351 found 2 days ago

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

September is typically the cheapest month to fly

From S$136 - S$279 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$242
Distance
940 km
Average flight time
2 hours 39 mins

Perfect flights from Washington to Chicago

Your Journey from Washington to Chicago

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Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including United, Delta, Southern Airways Express, 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$121 and roundtrip prices from S$242*.
 

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 . 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

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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$242. 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.

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