Looking into a late May-early June 2-week trip to Italy. We have no specific itinerary in mind, and are willing to plan the trip around what will be cheapest flight-wise. Are there specific cities that are cheapest to fly into/out of Italy? (from Denver)

Thinking open jaw would be best for exploring the country, but willing to arrive/depart from same city if that will get us a cheaper flight. I know that is highly variable, so I'm mainly just looking for an answer to the question above (if specific cities are known to generally offer cheaper flights; I've heard that may be true of Milan?).

Thanks, Fodorites!

Definitely fly open jaw. It makes no sense to return to a city in order to depart. It isn't any more expensive to buy one-way fares each direction.

Also, you have to factor in the expense of traveling back to the departure city, and perhaps staying in a hotel there for a night.

You will have to do some research on the pricing. It varies. Check on flying into or out of Florence. A few years ago, it was a good deal from Denver.

Also, flight times vary. I think in general, people recommend not departing from Venice, because flights leave very early in the morning.

BTW, your time-frame is a good one. You will most likely be in Italy before the weather heats up and the crowds gather. Our trip took place during May: Rome, Florence, Venice, Santa Margherita Ligure, Nice.
I was using Mileage Plus on United and discovered it was easy to get those tickets flying to Denver from Nice, France.

Go here: Matrix - ITA Software by Google and make sure the "round trip" tab is selected.

In the "from" box, put DEN. In the "to" box, put MIL,ROM,VCE (commas, no spaces) - that's Milan, Rome, and Venice.

Check the "See calendar for lowest fares" box, and put in, say, May 20 as the beginning of a month-long search, then push "search."

ITA will ponder for a bit and will then return the cheapest fares available at the moment. If you check back the next day, you might see different numbers; airfares are highly "dynamic." meaning they change hour by hour according to how the computers see things.

Don't worry initially about open-jaw options. If you see a decent price on decent days, you can drill down and try various origin-destination pairs on the specific days you're looking at.

Also think about pricing flights to more central locations, e.g. London, then look at short-haul flights booked separately. For example, using the system above, the cheapest flights I could see from Denver to Italy (either Rome or Milan) in late May were running $1500 or so round trip. On the same days, round trips to London were under $500, and round trips from London to Rome or Venice were $200 or less (and open-jaws would be similar.) If you choose that approach, just add enough time as a buffer at each end so that any flight delays or cancellations won't make you miss your connecting flight, which could prove expensive.

Fantastic advice, thanks so much! I did not know about that ITA tool. And after looking at more air fares this morning, I was just starting to think about the other idea you suggested (just get us to Europe, and then book intra-Europe flights separately).

You were a big help with our Scotland trip last year; thanks for helping again!

Matrix is very informative, more so than Google's own flights site. No ticket sales, though. To assemble an efficient multi-destination route you must use the multi-destination search function. Also, on the bottom of the opening page you can pick your currency from the default box.

We also follow the practice of getting to any European hub and then worrying about connections via low cost air or trains. The Matrix software Gardyloo helpfully guided many of us to has been fantastic IME.

June 2nd is a long weekend in Italy. Not likely to matter for flights from the US but the European short hops will likely be priced to reflect that. On the plus side for you next year it'll be a Sunday making it harder for people to take long weekends.

BTW I thought the new Google flights was basically a repackaged Matrix. What's not available on the new Google flights site?

Also flights earlier in the month are much cheaper at the moment

If you bother to learn it, ITA's "advanced routing language" is incredibly powerful - you can sort by alliance membership (important for loyalty programs) or use multi-city/multi-destination searches (e.g. Denver to Milan OR Rome OR Venice) or specify en-route transfer points, sort by arrival or departure times, and on and on. Google Flights does basically the same thing as Kayak (which by the way also uses ITA in its "back office.")

The first few I see on Google flights. You can choose between Star Alliance,One world and Sky team. I know you can pick countries Or multiple different airports. Connecting airports including connection times.

All with a few clicks