We will be in Cologne for a couple of days in December and need to get to Milan on Tuesday 12/12 for the Inter Milan match that day..

I have what seems like 3 options and none of them scream at me - this is the one. All work for our needs so I am not sure if any of them are any better than the others. Meaning are any of these 3 airports better to fly out of than the others?

Assume pricing is the same across the board (or at least really close - roughly $300 total)

1 - Cologne to MXP with a layover in Munich (75 mins). 9am flight arrives MXP at 12:30 Airport is 20 mins from our hotel by taxi.

2 - Cologne to Dusseldorf by train (55 mins). Dusseldorf to MXP with a layover in Frankfurt (50 mins). 10:50am flight arrives MXP at 1:40pm. Train station is a 5 min walk from our hotel.

3 - Cologne to Frankfurt by train (55 mins). Frankfurt to MXP nonstop. 9:00am flight arrives MXP at 10:20am. Train station is a 5 min walk from our hotel.

While we would love a later flight to get a little more sleep which the Dusseldorf flight gives I am not sure it makes a lot of sense to do it since it lays over in Frankfurt anyway.

The Frankfurt option seems decent other than being up early as there is a backup plan if needed (there is a 12:30pm direct flight in case the 9am doesn't happen or if our train is delayed getting to Frankfurt). There are also a few flights later to Linate so backup plan there as well if needed.

The Dusseldorf option has no back up plan except one flight about 20 mins later but goes to Linate which means a $100 cab to get to our hotel which is near MXP and has a free shuttle.

The Cologne option has several back up plans some to MXP some to LIN that are Lufthansa train+plane combo tickets. Most are more expensive but they are options.

Just not sure which airport is more of a pain to get in and out of especially if we are taking a train to either Dusseldorf or Frankfurt first. I assume on these trips we wouldn't get any special "security" benefits by doing this since we would still have to go through security at the airport after arriving on the train - correct?

Thanks for any advice you care to share. If you have other travel options that make more sense lmk also but these are what I have come up with.