When we end the Rick Stev's Venice/Florence/Rome tour on Dec. 24, 2008, we will be going to Milan and we fly back to the states from Malpensa. Any tips about train vs plane to Milan? Can you suggest a great place for 4 to stay in Milan? Should we spend the last night near the Malpensa airport due to the distance from Milan? If so, can you recommend a place to stay?
I would linger in Rome for two additional days before heading up to Milan. IMO, Milan isn't too thrilling and 4 days there is way too many.
From Rome Termini, you are only 4.5hrs away from Milan. Hardly worth 30 min to FCO and 2nhrs going through security for a 1.0hr flight. Christmas Eve scares me a bit however so I would have early train tickets on this one as it may be one of the few days a year when you might run up against a full train.
For your flight out of Malpensa, it depends on how early your flight is. From the Milan train station, the bus takes about 70-80 minutes to the airport. The earliest bus out leaves at 5:30am so if that doesn't get you there in time for a 2.0hr-2.5hr check-in, you may have to stay near the airport.
Air One is offering flights from Rome FCO to Milan Linate on 12/24 for 90.56 euro, but that's more than the cost of the train and would save you best case an hour of travel. Better to take the train, but do buy your tickets no later than upon arrival in Venice.
The train will be more convenient than flying. Since you are travelling around the holidays, I recommend buying your tickets and making your train reservations in advance. Trains in Europe can be jam packed around the holidays and if you are trying to catch a flight, you won't have a lot of flexibility to take a train on another date.