Travel from Milan back to the US

I always prefer to stay in a city rather that at an airport hotel. You can take the Malpensa Express train from Milano Centrale to the airport, departing at 06:25 and arriving at 07:17. The next train departs at 07:25 and arrives at 08:17. IMO, that's too late for a trans-Atlantic flight. The fare is €10. There are two shuttle bus companies that operate buses every 20 minutes between Milano Centrale and the airport. The trip takes about 50 minutes (the same as the train and for the same fare: €10).

At the end of the trip I typically stay near the airport. End of trip, tired, not wanting to go home, etc., so I will have a nice dinner in the city, then make my way to the airport at night rather than in the morning. I won't sleep the whole night before if I have to worry about making it to the airport in the morning with traffic, etc. Just a preference that makes my last day less stressful for me.

What time to you get into Milan? I think it's worth spending the day and the evening there and then getting to an airport hotel later that night. If you have one night in a hotel in Milan they should be able to hold your luggage for the day and you could pick it up before you head to an airport hotel. I find it much less stressful to be close to the airport for a morning flight, but that's just me.

That's why I don't like returning from Malpensa. Too far from the city. I have stopped flying back from Milan long ago. However now they have the Malpensa Express train from the Cadorna station (very close to the Sforza castle and the Duomo) which gets you there in just about half hour. That is where I would stay the night before. http://www.malpensaexpress.it/ In the old days, before Malpensa even had a train and the trip from Milan was over one hour by bus, I would stay in nearby Gallarate, just a few minutes from the airport by bus or taxi. Gallarate is a short train ride from Milan. I used to stay at this hotel. They had a pizzeria to die for at the time, haven't been there for over 15 years, though. It used to be called "La Vecchia Rotaia" (the old train track), now it's called "la nuova Rotaia" (the new train track). I guess they renovated it. http://www.lanuovarotaia.it/enter.html But given the fast train option from Cadorna station with the Malpensa Express, I think you should stay near the Cadorna station and take a train that gets you to the airport at least 2 hours before departure. Trains to Malpensa depart at 28 min and 58 min after the hour from Cadorna.

Thanks everyone for your help!