Cheap flight tickets from Washington Dulles to Chicago

Compare Washington Dulles to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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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 Airport to Chicago? If you want to travel next month, return fares start from RM701. 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 September.

Direct flights from Washington Dulles to Chicago

Washington D.C. to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRM349
Cheapest month to flySeptember
Average flight time2 hrs, 15 mins
Most popular airlineUnited
Average flights per week436

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 RM698. 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 15 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 June 2026, there are 436 flights per week flying from Washington Dulles to Chicago.
The cheapest month to fly from Washington Dulles to Chicago is usually August.
If you're flying from Washington Dulles Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from RM698.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Washington Dulles Airport to Chicago on Tuesday, 18 August 2026.
Yes – the average flight time is 2 hours and 15 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 June, the average temperature is usually around 19°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, Delta and United offer the cheapest flight tickets to Chicago.

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

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

  • Chicago is one hour behind Washington DC, where Washington Dulles International Airport is located. Chicago observes the UTC-6 timezone.

  • With 38 flights a week between the two airports, Washington Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD) is the most popular route. United Airlines operates the earliest flight at 06:10. If you'd like to get more out of your day before jetting off, the latest departure from IAD to ORD is with United Airlines at 22:20.

  • To avoid missing your IAD to Chicago flight, leave plenty of time to check in and find your gate. Arriving two hours before international departures and one hour before domestic flights is the general travel rule.

  • During popular months such as June, it's a good idea to get to the airport even earlier. Arrive two hours before a domestic departure and four hours ahead of an international flight when you fly during peak periods in general.

  • Direct Washington Dulles International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) is where you'll complete your journey.

  • Book your favourite seat with United Airlines. This popular airline operates direct flights from Washington Dulles International Airport to Chicago.

  • Located around 40 kilometres from the centre of Washington DC, IAD can be reached in about 45 minutes by car. The journey on public transport takes roughly 1 hour 10 minutes.

  • Searching for a hotel near IAD? If you're catching an early flight from Washington Dulles International Airport to Chicago, these accommodation options will put you moments from your departure lounge:

  • When it comes to the on-time performance of Washington Dulles International Airport, 77% of flights stick to their scheduled arrival time.

  • IAD is located at 1 Saarinen Circle.

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

  • RM349 is the cheapest price we've seen for a one-way Washington Dulles International Airport to Chicago flight. A return plane ticket right now is RM698. Depending on when you book and the availability, these fares may change.

  • Book five months before your departure date. Pricing trends suggest that this is the ideal window for finding cheap flights from IAD to Chicago.

  • October is the best month for picking up an incredible deal on Washington Dulles International Airport to Chicago tickets. If you want to travel during a different time of year, the 'Whole month' tool will show you the lowest prices for each month.

  • There's no need to check back in every day to find out if fares have dropped when you set up a Price Alert. We'll let you know the moment there's an even bigger deal on cheap flights from IAD to Chicago.

  • Snag an affordable flight from Washington Dulles International Airport to Chicago with the help of our filters. Choose your ideal duration, departure time and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometres. It takes about 30 minutes to reach the centre driving.

  • Getting there on public transport takes around 45 minutes.

  • The last thing you want is a long journey to your hotel if you're getting in late on a flight from Washington Dulles International Airport to Chicago. Reserve one of these accommodation options near ORD instead:

  • Lock in the best deal by reserving your ride from Chicago O'Hare International Airport around four weeks in advance of your flight from IAD to Chicago.

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

Chicago Midway International Airport (MDW)

  • Once your flight from Washington Dulles International Airport to Chicago has hit the tarmac, you can reach the city centre in about 25 minutes by car. Central Chicago is roughly 16 kilometres from Chicago Midway International Airport (MDW).

  • If you travel by public transport, the journey will take you 30 minutes or so.

  • You'll find some comfortable places ready to welcome you near MDW. Settle in and get cosy after your IAD to Chicago flight at any of these perfectly located options:

  • Snap up a deal by booking your ride from MDW four weeks ahead of time. You'll also have access to a greater selection of vehicles.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Make tracks for the city centre after your flight from Washington Dulles International Airport to Chicago has landed. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to reach by car.

  • If you're using public transport, expect a journey of around 2 hours.

  • Stay at a hotel close to RFD and go from landing to lounging in your room in a flash. Whether you have a late IAD to Chicago flight or just want to keep your travel plans simple, these accommodation options are all about convenience:

  • Booking a couple of weeks in advance of your flight from Washington Dulles International Airport to Chicago is a smart way to go. As well as better deals, you'll get a better selection of vehicle makes and models at RFD.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • July is the most popular month for flights from Washington Dulles International Airport to Chicago. To avoid the crowds, visit Chicago in January.

  • Lock in a Washington Dulles International Airport to Chicago plane ticket with a departure in July if you're eager to experience the city during its warmest month. Expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).

  • For cooler conditions, look for a cheap ticket from IAD to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of the United States

  • Chicago has plenty going for it, but there are so many other corners of the United States you should also see. Around 451 kilometres southeast of Chicago, a visit to Columbus will fill your itinerary to the brim. Check out popular attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • If you're ready to explore another great destination in the United States, head for Indianapolis, roughly 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are key reasons to visit.

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