Flights to central Europe...which one ?

If you had a short trip, the cheap option would waste a lot of time just getting to the area you want to visit. But since you have over a month..... it's certainly a consideration. And I believe you have the possibility of a night train between Venice and Vienna, which could free up some day time sightseeing.

The savings are enough that I’d pick flying to Venice and home from Vienna. Venice is special enough to see again.

Almost 20 years ago (has it been that long?!?!) on a trip that included parts of Central Europe, we flew in to Venice, then rented a car there to see some of Slovenia and Croatia, before returning to Venice, where we’d been on a prior trip.

We have done the same in a previous trip : fly yo Veniuce to see Slovenia, Croatia and the Dolomites...great trip !

Night train could be an idea but it's costly ! More than a room in Venice and the train ticket !

It would help to know approximate dates/time of year and planned itinerary. Thr round trip to Vienna suggests some backtracking - open jaw/multi-city airfare to the first and last cities may work out to being more economical when you figure in costs of land arrangements.

Are the quoted prices CAD or USD?

What locations are you planning to actually visit, or at least a rough itinerary? Without knowing that, it's hard to help you narrow down the best places to fly in and out of. Personally I try to minimize backtracking as much as possible, even if it costs slightly more.

Thanks for the help !

1) prices are in cad
2) our trip would be somewhere between june 30 and August 18 2025
3) we would do Austria (Maybe Venice Innsbruck Vienna by train), Slovakia (rent a car in Bratislava), Krakow and southern Poland and Hungary.

I would book the cheaper option and the take flights from/to Venice assuming you can get a low cost carrier. I don’t think the minimization of backtracking or getting straight to your destination is worth the extra 50%

Over the last few years on 3 occassions I have tracked prices from Texas to Central Europe. Between 200 and 300 days out I looked for the best cheap flight (one change max and 2 to 4 hour layover) and then had Google Flights send me updates on the prices The prices bounced all over the place, but they all were at their cheapest between 4 and 6 months out. But what was more interesting is that flights that cost more when I started my search often became the lowest cost flight. Fortunately Google send you updates on those too. All I learned was to wait till 4 to 6 months out and use the cost matrix where you can see if moving things one day at one end of the trip or the other end of the trip will produce a savings. Google's date/cost matrix always sets my travel days.

If the direct flights are such that I had to cut a day out of my vacation to pay for them, well, the first day with the Venice connection is also a day out of my vacation, so it breaks even.

So flying to a place that would require an entire lost day and require a hotel in a town I wasnt interested in plus the communte from the airport and to the train the next day is more underutalized time: I wouldnt do it. But this always comes down to personal values. There is no wrong.

But, if flying to Budapest or Vienna or Krakow all cost about the same, then maybe an open jaw would also cost about the same. Nothing more efficient than heading in just one direction. And there is always the economy option. Dont know what sort of tickets you are looking at, but one or 2 with a checked bag and the others with carryon only might assist with the price. Its how I took my two kids on their first trip to Europe. We played the carryon and personal item to the hilt (but within the rules).

I also dont drive on holidays. Well, I did it once and it wasnt pretty. I am on holiday. And the cost of a car can multiply fast, the rental fee is only half the cost (okay 65%). Then to avoid the drop off charge I would end up back tracking. Okay if it were a tight region to be seen and a loop really works without detracting from the overall enjoyment, but when crossing a lot of real estate I dont want to go back. First I would see if I would get as much personal value out of trains mixed with a few private tours. If its close, equal or only slightly more thats the way I would go.

I guess what i am saying is that the equation is greater than the ticket cost and only you know the parameters for your best and most enjoyable holiday. What works and worked for me just wont work for everyone so all i can offer is things to think about, but no answer.

I will ramble a bit more.

Dont let the plane tickets drive the holiday. Develop a budget for the entire trip, then get creative in where you go vs an extra day of travel with little enjoyment benefit. Austria is silly expensive so two days less in Austria and two days more in Poland or Slovakia or Hungary might just pay for the tickets ... or a big chunk of it. Train to the heart of Slovakia and only rent a car for three days to reach the hard places using a home base someplace (save on unpacking and packing too). A couple of days less car will offset the budget bust because of plane tickets. No single thing you have to buy shoudl be driving the journey as long as a fun result can be created within the budget.

There was some discussion about where was cheap for a trip and where wasn’t. I did some digging around and found a few sites. They all had more or less the same rankings give or take a place or two. Just more to ponder.
One site out of 193 countries listed this:
Ukraine, (ranked 11th in the world and cheapest in Europe), Poland (ranked 61st in the world), Montenegro (ranked 65th, the cheapest country using the Euro), Hungary (83rd), Slovakia (ranked 91st it’s the cheapest country in the Eurozone), Portugal (Cheapest country outside of the old Soviet Bloc at 94th in the world), Italy (ranked 150th), Canada (ranked 169th), Austria (171st), United States (ranked 184th), Switzerland (rated 193rd and the most expensive place to visit in the world).

Mr. E has given some sound advice. Given your location choices, I would pick an airport much closer to what you want to see, and not Venice (even if it's "cheapest" now, it may not be in a few months). Since you have time, start tracking various flight options using Google Flights. Definitely look at both round trip options and open jaw (in one city, home from another) to minimize backtracking. Given time of year, I'd maybe start south and move north, just due to potential summer weather (impossible to predict now of course).

Thanks for all the help.
Just want to add that we have been in Europe six time (with and without the kids) in the last 15 years.

Si open jaw tickets, not drop the car in another country, use train and travel light is already stuff we know.

We always travel with carry on only. So we need Airbnb. That’s why we like to book flights ahead so that was we can access to the most well rated Airbnb which, to us, is a must.

Flights cost is always a bit of a gamble as everyone know.