Getting to Venice from US

Umm, ...Why not fly to Venice?

Flying to Milan is fine if you plan to spend some time there before heading to Venice.

We flew to Milan and spent a few days at Varenna on Lake Como, then rail to Venice..

Use Google Flights to see what your options are. Just enter Chicago as the origin and Venice as the destination. If you don't have plans on this trip to sightsee in Milan, I'd at least price out connections that get you to Venice itself. Perhaps the cost difference will not be great.

A non-stop to Milan will put you at Malpensa Airport, I think, which is quite a long ride from central Milan, where you'd need to go for a train to Venice. It would be a different story if you were in Milan for a few days of sightseeing.

If you don't have the time/interest for Milan on this trip and the Chicago-Venice routing is cost prohibitive, you'll be in a tricky position, schedule-wise. It's impossible to know how quickly you'll be able to step on a train in downtown Milan. In that case, I'd try to get a train ticket that permits changes, though you'll still be responsible for any fare difference.

Is this the Venice Florence Rome tour or a different one?

When I did the VFR tour, I flew direct from DC to London Heathrow, spent the night, flew to Venice the next day. Return flight was from Rome to London (spent weekend), then DC. All on British Airways and FinnAir (BA's partner out of Rome). You could also do a no-overnight-layover flight from Chicago to a UK/European hub and then catch the flight to Venice. I purposely spent extra time in London.

No, flying into Milan is not the best way, flying to Venice is. There’s a whole slew of airlines out of Chicago that fly to a major hub with a connection to Venice. Check google flights and take your pick…

You can also fly into Florence, take the tram into town and then a fast train to Venice from the Santa Maria Novella station.

I flew in to Venice & flew home from Milan when I took the Village tour. I flew from MSP and I think I connected going in CDG & through Amsterdam maybe coming home.

If there was a non-stop from Chicago to Milan, then I'd say it would be 50-50 to
take the nonstop and then the 2 hour train, or to connect and fly to VCE.

But the seasonal non-stops do not start until April, so a connection to VCE
seems to be the better option, schedules notwithstanding.

Because your RST begins and ends in different cities, I'd advise choosing a multi-city itinerary - to Venice and from Rome for instance, with initial outbound leg being international as I prefer connecting in Europe (or the UK). Both directions, I want minimum 2.5 hour layover time; regardless of airline, routing and airports used. I'll spring for at least premium economy, want to advance seat assign, check a bag which for me is usually on my return due to wine and olive oil purchases and would avoid a carrier using single aisle jet for the long haul flight. I'll check out the seat map as I'm searching flights and like Airbus jets with the 2 - 4 - 2 seating, so I can be in a 2-seat row. I'll avail myself of each airport's layout map, checking position of terminals arriving in / departing from to know what intra-airport transportation, if any, I could be taking. I check both aggregators such as Kayak and individual airline websites when looking and will be ready to purchase when all of my wants are provided at a fare I'm willing to pay. Hope you enjoy the planning and have a great tour!

Thanks all for your help.
Happy travels to you, too.

Google Flights is a great resource for researching flights. I agree with above, get yourself over the pond in one flight. If anything happens with the connecting flight, there are lots of options, once you're in Europe.

We found flights into Venice, as charming as they are, to be much more expensive than flying into Milan. It's not a bad idea to spend the night in Milan, close to the Central train station, if your flight lands in the evening. Hotel Berna is a great one-night option in Milan, less than a block from the train station. Then refreshed, take the train to Venice the next day. Always plan to arrive a day or two before the tour, in the event of flight disruptions.

Whatever you decide, always purchase flights directly from the airlines. Don't use third-party vendors, such as Expedia or Kayak. If a flight gets canceled or delayed, you have major issues with third party vendors.

And do book a multi-city (open jaw)ticket: into your first destination, and departing from your last destination.
Have a great trip!