Best flight route to get to Milan from DC

American Airlines operates a seasonal nonstop flight from Philadelphia to Milan Malpensa that might be the most convenient for you if you're traveling when it's operating (this year late May to mid-October).

Otherwise, yes, your main realistic option for flying nonstop is via the New York metro area (Newark or JFK). United has a seasonal flight from Chicago and Delta also operates from Atlanta, but I can't imagine either of those makes sense to drive to from the DC area.

I’d look for a flight connecting in Europe. I’d choose a flight out of IAD connecting via Zurich or Munich; those are both good airports for connections.

And both are close to Milan, relatively speaking.

Rome is close, only just over 3 hours by frequent fast trains once you get to Termini. MXP was built to be a big intercontinental airport, but then Alitalia changed their minds and shifted to Rome, then went under. MXP is really underutilized, and Milan is the business, financial, and fashion capital of Italy.

A lot of people in the Dolomites use MU.C for direct flights to the States. United has direct flight to Venice in the summer from IAD

IAD is a United hub and United is a Star Alliance partner of which the Lufthansa Group is part (also Swiss and Air Dolomiti are owned by the Lufthansa Group).

There are many possibilities but given the above facts, flying with United or its Lufthansa Group partners via Frankfurt, or Munich, or Zurich will offer the most options. Milan has two international airports (Malpensa MXP and Linate LIN), both have flights to the aforementioned European destinations, therefore check which airport makes sense for you. Linate is much closer to the city center.

What are your dates?
American direct to Milan from PHL begins 5/23.

We are almost equidistant from IAD and PHL and much prefer PHL. Hate Dulles.
We have also driven to Newark few times for direct flights. About 3.5 for us. Easy airport to use and would rather that drive than deal with Dulles!
Depends where in DC area you are.

Ditto above- if you have to change- make the change in Europe. At least you are IN Europe if any snafus.
Zurich would be my choice. Munich or Frankfurt OK

We are almost equidistant from IAD and PHL and much prefer PHL. Hate Dulles.
We have also driven to Newark few times for direct flights. About 3.5 for us. Easy airport to use and would rather that drive than deal with Dulles!

Christine, I'm curious as to why you dislike Dulles and what makes Philadelphia better in your opinion. I really like Dulles, but am open to being persuaded. :) I also wondered what you do with your car when taking a longer trip overseas. The garage fees really add up and I'm too far from any airport to Uber!

OP, I've done direct flights from IAD to Rome as well as flights to Florence with a layover in Lisbon, which wasn't difficult at all. As someone else mentioned, getting from Rome to Milan by train is pretty straightforward if you're trying to avoid a connecting flight. I've never flown into Venice, but have taken the train between Milan and Venice and it was a pleasant trip. I haven't been in the Munich airport, but have seen it mentioned here before as a good airport for connections. Zurich seemed organized when I was there too.

For what it’s worth Boston is just starting direct flights to Milan in May and that’s what we’ll be taking when we fly into Italy at the end of May. It’s a huge change from having 24-36 hours of travel time be cut down to less than 15 hours from the time we leave home. As former NYer’s we always took for granted the direct flights from JFK so having this from Logan (one of the most disorganized airports in North America) is a game changer. I know Boston isn’t close to DC but it’s still an option.
This part goes to Roberto Da Firenze: actually there’s three international airports in Milan, because don’t forget about Orio Al serio, Bergamo, which is having some major infrastructure works and changes going on currently. No, flights from North America don’t transit directly through it, however, flights from other parts of Europe DO transit through and to it. In 2018 when we vacationed in Sicily we flew from Boston through Frankfurt and it landed in Bergamo at the end which is much closer to my father-in-law’s home near Lecco than Malpensa or Linate.

If it's not too difficult to get to JFK, Emirates has a nightly non-stop to Milan - Fifth Freedom Flight.

With a layover in Europe I would go for a flight to Milan Linate.
Frankfurt and Paris CDG have the most frequent connections to Linate, and both have flights to IAD.
No flights to ZRH from Linate.

Thank you everyone, After much debate, we've decided to fly out of IAD to Zurich and connect to Milan We have always found the Swiss transportation systems to be well-run and on-time. The train apps for Switzerland and Italy are very helpful to have on your phone.