Geneva to Milan OR Geneva to Zurich to Milan?

From Grand Rapids, I would be sorely tempted to drive to O'hare and take the Swiss nonstop to Zurich.
Simplest would be to go from Zurich airport to Chur, then Chur to St Moriitz or Pontresina. Then To Tirano on the Bernina Express, then Tirano to Varenna on Lake Como. Then you are just one hour from Milan on the hourly train.

Another option would would be to go to Luzern from Zurich airport and stay for a couple nights, then take the Gotthard Panorama Express to Lugano. That starts with a lake boat ride to Fluelen on Lake Luzern (the Vierwaldstaettersee) connecting to a train over the Alps to Lugano. Then you are just 1 1/2 hours from Milan.

It makes more sense to fly into Zurich. Geneva is not that beautiful. It looks great flying over the lake before landing though.
You could fly into Zurich and from the airport take the train direct to Luzern. Spend a couple of days in Luzern and then take the train to Interlaken via the Brunig Pass. This is the scenic route the Golden Pass Line travels. At Interlaken transfer for the train to Lauterbrunnen. Either stay in Lauterbrunnen Valley or one of the alpine villages of Murren or Wengen, both have beautiful views of the mountains and the valley. Then you can continue south to Milan. Here is a previous post about how to accomplish a scenic rides from Interlaken to Milan
https://community.ricksteves.com/travel-forum/italy/best-train-from-italy-milan-to-interlaken

Lake Geneva is beautiful, especially around Montreux, but Geneva itself is gray and not that inspiring. So if you do land at Geneva, I'd head straight to Montreux, then Zermatt, then on to Milan.

Both of these suggestions are extremely helpful to me. Since we have a large stash of AA miles, we will most likely use some to simplify things and fly out of GRR which eliminates the drive (and paying to park for a month or so).

I see the wisdom in your recommendations to make it easier by flying into Zurich and skipping Geneva. I just have read differing opinions (as always!) about Zurich vs Geneva but based on this input, I think we will delete Geneva from our itinerary.

One more recent thought--we can actually do a little better flying into Frankfurt so thinking of maybe doing that for just 2 nights with a quick day trip to Heidelberg, then moving on to Zurich by train. I like the ideas of staying in a smaller town vs. Zurich and also the stop at Lake Como.

Thank you for your help and feel free to comment on the above if appropriate.

I am confused by this: Another option would would be to go to Luzern from Zurich airport and stay for a couple nights, then take the Gotthard Panorama Express to Lugano. That starts with a lake boat ride to Fluelen on Lake Luzern (the Vierwaldstaettersee) connecting to a train over the Alps to Luzern. Then you are just 1 1/2 hours from Milan.

I really like the idea of spending a few days in Luzern (same as Lucerne, right?) and also like the idea of the boat ride on the lake that connects to the train, also like the idea of a stop in Lake Como. Is there a way to also do the Bernini Express and incorporate all of these things into one itinerary?

Don't try to cover too much. You will wish you had more time outside in the natural beauty of Switzerland.
Zurich and Frankfurt are big business towns.

Sorry, typo there, should be "over the Alps to Lugano". I'll edit.
Hey, they both start with "Lu".
Both routes go over the Alps, so if you are going to Italy, you'd go over, then back, then over again. Nothing wrong with that if you like crossing the Alps just for fun.

Just to clarify--not really interested in either Frankfurt or Zurich per se--looking at them only as places to fly into and as a starting point for scenery and smaller towns that interest us more.

If you want to get to Switzerland from Grand Rapids with just one plane change and using AA points, you have to fly into Zurich.

GRR-CLT
CLT-FRA

Then train from FRA to Zurich?

Does this simplify what I am trying to do?

GRR-CLT-FRA

2 nights in FRA, then train to Zurich

In Switzerland: best options for a great small scenic town to stay in (rather than actually staying in Zurich) and then best options for scenic way to get from this small town to Milan.

Bonus requests: take Bernini Express
stop in Lake Como (or would it be easier to do a day trip while we are staying in Milan?)