Driving to MXP from Lake Como early Sunday morning. Time?

I would stay at an airport hotel for a flight that early
Too risky

Even on Sunday?

Not sure we can go that night - we're going to a wedding Saturday evening that probably won't end until 11............ Can you check into a hotel at midnight near the airport?

Yes
Even on Sunday

Can you change flight to leave on Monday?

No way would I plan on leaving from Menaggio with a morning of my flight out of MXP. Yikes. Too much can go wrong.

It's up to you, since there is always some risk.

Traffic is usually not a big issue on Sunday morning, but one could encounter road work or an accident or one could have a mechanical problem. For example a year ago my drive from Arezzo to Fiumicino airport (normally 2 and 1/2 hour) turned out to be a 6 hour drive due to a fatal accident near Orvieto. I was stuck for hours unable to move together with hundreds of motorists. Fortunately I was driving the day before my flight.

Normally the drive Menaggio to MXP (I've done the opposite way upon arrival) would be 1.5 hours, to which you should add at least 30 min for refueling and car rental return (and maybe some leeway time for possibility of getting lost). Also be aware that the route Menaggio-MXP entails travel on the toll freeway A36 Pedemontana Lombarda. It's a toll freeway but you will not see any toll booths. The license plate will be photographed at the entry ramp and then you need to go online and pay toll in this website within a certain specified number of hours (don't remember how many). It is therefore important that you keep record of your rental car license plate number and vehicle model and color. Take a picture of it.

Yikes- now I’m really stressed! The situation is that we’re going to my nephew’s wedding on Saturday night near Menaggio, and the wedding is an evening wedding so not over until late, and Monday there’s a celebration of life for one of my best friends who passed away recently, so Monday isn’t an option.

So I guess we Weill be leaving super early - maybe 4:30 or 5, and hope for the best.

If we do decide to get an airport hotel after the wedding, does anyone know if you can check in super late- like midnight or later?

As long as hotel has a 24 hour desk you can check in late
I’d expect airport hotels would all allow it
Email and ask

I would be inclined to drive to MXP the night before, after a final dinner in Menaggio.

Getting up around 4AM is quite unappealing to me. If you do choose to do the AM departure, I would aim for wheels in motion no later than 5:30

We have a 10:40 flight at MXP, final destination the US.

What is the intermediate stop? This will affect what amount of time you need at MXP for departure.
If the transfer point is LHR you need extra time for the Schengen exit process. If the transfer is AMS, less time is needed at MXP as the Schengen exit would happen at AMS.

My $0.02

Thank you so much for the information about the toll! I would have never known!

What is a Schengen exit process? Our layover is in Paris and then on to the States.

I wouldn't want to drive late after a wedding, but, there is a hotel at the airport, which was suggested to me by someone on this site, because my departure in October is on a 6 am flight. Check out the Sheraton Malpensa.

If you are going to Paris CDG, then as long as you are in line at check in by 9:10am (at least 90 min prior to departure, but two hours better), you will be ok.

So if you decide to leave in the morning, try to leave before 7am.

The toll must be paid within 15 days from the time of transit on the freeway A36. So you can do so from home. I think I paid by credit card at the time (within a day I think).

Your 'fixed' events, do restrict your options.

The good news is your flight from MXP is to Paris, so being at MXP 2 hrs prior to departure, should be sufficient. A 6AM departure should work, barring some random road blocking event, meteor strike or earthquake.

I used the term 'Schengen exit' to cover the border control - passport exam process. Basically going through a line and passport exam like entering, but for the exit.
In your case that happens in Paris. As long as you have a single ticket from Milan-Paris-US, the airline has built in enough time to do that in Paris.