Flight tickets from Washington Dulles to Chicago

Compare Washington Dulles to Chicago flight deals

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Flight deals from Washington Dulles to Chicago

Looking for a cheap last-minute deal or the best return flight from Washington Dulles to Chicago? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Washington Dulles to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Washington Dulles to Chicago flights are currently cheapest in October.

Direct flights from Washington Dulles to Chicago

Alternative Washington Dulles to Chicago routes

Looking for the cheapest, fastest or easiest route from Washington Dulles to Chicago? You could fly into the following airports instead.

Washington D.C. to Chicago: Flight information

The things to know before you go.
Cheapest flight found₹ 6,321
Cheapest month to flyOctober
Average flight time2 hrs, 8 mins
Most popular airlineUnited
Average flights per week579

Finding cheap flights from Washington Dulles to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Washington Dulles to Chicago is ₹ 12,398. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 7 minutes is the average flight time from Washington Dulles to Chicago.
United, Air Canada and Air New Zealand fly direct from Washington Dulles to Chicago.
As of September 2025, there are 579 flights per week flying from Washington Dulles to Chicago.
The cheapest month to fly from Washington Dulles to Chicago is usually October.
If you're flying from Washington Dulles Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from ₹ 12,398.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Washington Dulles Airport to Chicago on Wednesday, 22 October 2025.
Yes – the average flight time is 2 hours and 7 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In September, the average temperature is usually around 18°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Frontier Airlines and United offer the cheapest flight tickets to Chicago.

Flying from Washington Dulles International Airport (IAD) to Chicago: what you need to know

  • Take a direct flight from Washington Dulles International Airport to Chicago and you'll be in the air for an average of 1 hour 55 minutes.

  • The timezone in Chicago is UTC-5. The city is one hour behind Washington DC, where Washington Dulles International Airport is located.

  • Washington Dulles International Airport (IAD) to O'Hare International Airport (ORD) is the most traveled route, with 37 flights a week to choose from. If you have things to do before heading off, the last flight from IAD to ORD is with United Airlines at 22:20. Choose the first departure with United Airlines at 06:10 if you want to fly out earlier.

  • To avoid missing your IAD to Chicago flight, leave plenty of time to check in and drop off your luggage. Turning up two hours before international departures and one hour before domestic flights is the standard rule.

  • Taking off during a peak time like public or school holidays? Expect longer queues at check-in and security. To give yourself peace of mind, arrive up to four hours before international flights and two hours ahead of domestic departures.

  • Start your trip at IAD and fly nonstop to O'Hare International Airport (ORD). That's where you can expect to land when searching for Washington Dulles International Airport to Chicago tickets.

  • United Airlines is a popular carrier that operates direct flights from Washington Dulles International Airport to Chicago.

  • Travelling from central Washington DC to IAD takes around 1 hour 10 minutes on public transport. If you drive, ride-share or grab a cab, you'll cover the 40 kilometres in 50 minutes or so, depending on traffic conditions.

  • Catching an early flight from Washington Dulles International Airport to Chicago? Avoid rushing to the terminal (and enjoy a little extra shut-eye) by choosing one of these hotels near IAD:

  • Of all flights leaving Washington Dulles International Airport, 74.39% arrive as scheduled at their destination.

  • IAD is located at 1 Saarinen Circle.

How to find the cheapest flights from Washington Dulles International Airport (IAD) to Chicago

  • ₹ 6,321 is the lowest price we've found for a one-way Washington Dulles International Airport to Chicago flight. A return ticket right now is ₹ 12,398. Depending on when you want to go and the availability, these fares may change.

  • To pick up cheap flights from IAD to Chicago, reserve your trip six months ahead of your planned departure.

  • Plan your trip for October. That's the best month for scoring an awesome deal on Washington Dulles International Airport to Chicago tickets. If you're flexible on when you fly, use the 'Whole month' tool to find the lowest price across each month.

  • There's no need to check back constantly to find out if fares have dropped when you create a Price Alert. We'll update you the moment there's an even bigger deal on cheap flights from IAD to Chicago.

  • Pick your preferred arrival and departure times, airlines and number of stops with our filters. Then, sort the results for your flight from Washington Dulles International Airport to Chicago by 'Cheapest,' 'Fastest' or 'Best.'

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It'll take you about 35 minutes to get to the centre driving.

  • If you're travelling on public transport, expect a journey time of around 55 minutes.

  • Look into staying at a hotel near ORD if you're coming in on a late flight from Washington Dulles International Airport to Chicago. Select one of these accommodation options and avoid the hassle of a long transfer:

  • Travel at your own speed with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and see more of Chicago and beyond.

  • For the best deal, book your ride from O'Hare International Airport about four weeks ahead of your flight from IAD to Chicago.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is about 19 kilometres from Chicago Midway International Airport (MDW). After your flight from Washington Dulles International Airport to Chicago has landed and you've made your way out of the airport, the drive should be around 20 minutes.

  • If you travel by public transport, the ride to the centre will take you 45 minutes or so.

  • Place the 'Do not disturb' sign on your door and unwind at a hotel close to MDW. Here are a few options where you can check in after your IAD to Chicago flight:

  • Forget about public transport schedules or long cab lines. Grab a Chicago Midway International Airport rental car and let your trip unfold on your terms. Check out the rates and availability from Dollar, Hertz and Budget.

  • Get first dibs on the best options. Booking your ride from MDW four weeks ahead of time often means more savings and a greater selection of vehicles.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 137 kilometres from the centre of Chicago. It'll take you about 1 hour 25 minutes to get to the city centre by car after your flight from Washington Dulles International Airport to Chicago.

  • The journey will take you roughly 4 hours 15 minutes on public transport.

  • Choose a hotel close to RFD and go from the plane to your bed in a flash. Whether you're arriving on a late IAD to Chicago flight or just want to keep your travel plans simple, these accommodation options offer convenience when you need it most:

  • Be in control of the next leg of your trip by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National will get you on the road.

  • Rental agencies sometimes offer deals on early bookings, so secure your vehicle from RFD a few weeks ahead of your flight from Washington Dulles International Airport to Chicago. A little planning can save you money.

  • Chicago Rockford International Airport's address is 2 Airport Cir.

Best time to go to Chicago

  • Travel to Chicago during high season if you like a lively atmosphere, but remember that prices are generally higher. Alternatively, book your flights from Washington Dulles International Airport to Chicago in the off-season when prices are cheaper and it's not as busy.

  • Book a Washington Dulles International Airport to Chicago flight ticket with a departure in July if you want to experience the city during its warmest month. You can expect temperatures to range from 15ºC to 29ºC.

  • January has average temperatures of between -12ºC and 3ºC. Look for a cheap ticket from IAD to Chicago around that time if you like cooler conditions.

More about Chicago

Explore more of United States

  • You've seen Chicago, now it's time to explore more of United States. Journey about 451 kilometres south-east to Columbus to check off its popular sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you'll have a packed itinerary ahead.

  • Indianapolis is another essential stop in United States and is around 257 kilometres south-east of Chicago. No journey is complete without experiencing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.