flying early morning out of Milan or Bologna??

MXP is a ways from town. The easiest way for you in either city is to catch a cab, that gives you the most flexibility. If you are going to the Dolomites in the future fly in to Venice, not Milan (it is all the way across the country). I would do Bologna this trip.

City center Bologna is closer to it’s airport;Milan MXP is far out of the city.

Where are you going to be, is really the issue/question.

MXP is not 'painful' to navigate and I found a nice hotel near the airport (with free shuttle) to get us to MXP for an early departure.

I have not been through Bologna, so cannot speak from experience about it.

I think you should choose based on where your trip is otherwise ending

It is a solid hour via train or bus from Milan to the airport. The train runs every 30 minutes. Are these flight directly back to the US or connecting flights to the direct flight? Big difference on when you have to be at the airport.

This is really helpful! I have been to Italy some ten times over the twenty years, so the focus of this trip will probably be some smaller/mid-sized towns where I have not been before (thinking maybe Arezzo, Padua?) and revisiting maybe some that I loved (Lucca, Ravenna?). And also a return to Venice just because it's Venice and I love it! In late Dec., early January, I'm guessing that some smaller towns where I'd like to go may be more "closed down" (Spello? Gubbio?) but further research and wisdom from you all will help me figure that out. (Been to Orvieto 3 times so probably skipping it.) I'll spend probably 3 nights in Rome, to start, then head north. To bookend the trip, though, I'm making the plane reservations while I can find the "cheaper" awards plane tickets, and then will fill in the towns to visit. I plan to end with two nights in either Bologna or Milan, in order to at least have a full day in that city before flying out. I figure that with the speed of the freccia trains, and given that I'll be in the northern part of Italy already, coming from Tuscany and/or Umbria, it really isn't a very big difference in time or cost (??) to travel from, say Padua or Arezzo to either of the departure cities. And thus, my question. I really have a limited budget, so if I CAN take non-convoluted public transportation to the airport (and if there is a significant cost difference because of distance from the city center), then those are helpful factors that I'd like to consider when deciding whether to fly out of Bologna or Milan. But I do need to check trenitalia website to ascertain if my guess about freccia costs are correct...

Oh! Good question about connecting flights. Both flights connect in Vienna to the same Air Canada flight back to Toronto (from whence I then wing homeward to New Orleans). What time difference do you see that making?

I would take the latest flight from the airport with the least security hassles--Bologna.

Just be glad you don't have one of those 6:00 am flights out of Italy. It is bad enough having a long flight to North America without having to get up at 3:30 am and then sit in airports until midday to leave Europe.

Thanks, all. Looks like Bologna it is.

....What time difference do you see that making?..... It is a big difference as to when you have to be at the airport. If it is a direct flight to US, you need to go through exit immigration, etc., so you need to be at the airport somewhere around the three hour mark - maybe as late as 2.5 hours but still very early morning. With a standard European domestic flight, then an hour and half at that time of morning is adequate for just having to go through security.

Bologna.
20 min by taxi from city center. Plus you leave half hour later. Airport is smaller too.

If you decide on Milan, you should find a hotel at the airport, because the city is too far.

Which airport in Milan - Malpensa or Linate? If your fight option to Vienna is from Linate, it's very close to central Milan and is also a smaller airport.

You can get tto the Bologna airport by a local bus, airport express bus or taxi. All are pretty resaonable. By the way, Bologna is well worth seeing- beautiful historic city with wonderful sites and food.

Bologna is a small airport, so you probably need less lead time there than Malpensa. Bologna is a good base for day trips too - Padua, Ravenna (especially a return visit), Ferrara, Modena and more - if you don't want to move around quite so much.