Land at MXP at 14:00 and get to Venice that day?

It takes an hour to get from MXP to Milano Centrale on the Malpensa Express
You have just 2 hours and 45 min to work with from wheels down IF your flight arrives on time

It’s possible I suppose but could be quite stressful
I’d plan to stay in Milan and book early am train in advance- no chance of missing that

Hotel Berna and Hotel Garda are both near Centrale and close to tram and usually not too expensive

If you spend arrival night in Milan you may have time to see the wonderful Duomo. If you're up decently early the next day, you might even get to see de Vinci's The Last Supper. We stayed at Hotel Garda - with a metro entrance at the end of the block to get to the Duomo - a bank ATM on the same street and an easy walk to the train station the next day.

The prospect of arriving in Venice any earlier than 830-900 PM look very slim. Even at that time of year you will looking for your lodging in night time conditions. I think a night in Milan would be a good choice.

See the Duomo and wander the Galleria, have dinner and be refreshed and ready for the next day.

You can use the 'search box', above to search " Milan Hotels" and get lots of options.

Hotel Berna seems to show up a lot.

I think it's helpful to build less stress into your travel. Is there a reason you need to rush to Venice? You have to spend the night somewhere. I'd book a room near the Central station. That's what we're doing in May. Realistically, it might be 5 o'clock before you get into Milan. If there are flight, baggage or customs delays, no worries. You could check into your hotel, take a walk, have a good introductory dinner and fall into bed. In the morning, you'd be rested, less jet-lagged and ready to adventure. You might check a few things off your Milan list before you get on the train. It's a couple of hours to Venice. Once there, you could hit the ground running with a clear head and a day in front of you. Be kind to yourself. Personally, I wouldn't want to be wandering around Venice jetlagged, in the dark, trying to find a hotel but that's me.

Thanks everyone -- this makes a lot of sense. I just had to mentally shift from "I don't want to spend another day in transit" to "We could have a relaxing evening and see a little bit of Milan." And I definitely don't want to be wandering around Venice in the dark, exhausted, searching for our AirBnb!

Check your Airbnb confirmation. It's not a hotel. Sometimes, if you don't check in by a specified time, they don't want to see you.

Why don't you take the direct train to Venice by Italotreno that departs from Milano Centrale at 18:45? You'll have to install 2 apps, the moment it's obvious that you can't take the 16:45 train open Italo's app and click buy.

Anyway I'd be quite surprised if Trenitalia's summer post-covid schedules were not better than the winter with-covid ones.

Since it's an Airbnb, your ability to reach it before it gets too late to get in (unless there is a key box or something) depends how far from Santa Lucia station you are staying. If you are close (for example in San Polo or Cannareggio), a train around 6-6.30 would get you to the flat before 10, which seems reasonable. If you are on the other side of town, then maybe not.

I haven’t reserved the Airbnb yet, so I don’t need to kill myself trying to get there in time. I’ll just make a reservation starting one day later. Thanks!

Wise move. Finding places in Venice in daylight can be challenging. After dark . . . . well, let's just say you should avoid it if you can.

On our last trip and first time in Venice, we got into Venice in the late afternoon. Because I had add another night in Venice to our itinerary (good choice), our original hotel reservations didn't start until the next night. It was more pricey by the time we made the change and we decided to do something interim. We had traveled from Cinque Terre to Milan to Venice. We stayed, in faded grandeur, at a hotel very close to the Venice train station. For pluses, it was easy to access, had a very nice breakfast and a marble entrance and ground floor bathroom with a plexiglass sink with fish in it. (Weird but cool.) While it wasn't baaaaad, it validated all our other hotel choices.

We all have different styles of travel. My travel style is that I can put up with a bit of uncertainty, as long as I know where I'm going to sleep. Personally, I'd take a break in Milan but that might not be what you want. However, I wouldn't depend upon a late check-in at an Airbnb. It might be worthwhile to book a hotel with a 24-hour front desk.