In 2026, Milan (MXP) and Rome (FCO) consistently rank as the cheapest cities to fly into from the United States, with Milan often holding a slight edge for East Coast departures. Because Milan is a major business hub and a base for low-cost European carriers, there is intense competition among transatlantic airlines, often driving "Economy" round-trip fares as low as $350--$450 from hubs like New York (JFK) or Boston (BOS). Rome is also highly competitive due to the sheer volume of tourist traffic and the expansion of ITA Airways and Neos. For travelers coming from the West Coast (LAX or SFO), Rome and Milan remain the primary entry points with the most "direct" and "one-stop" options. A smart strategy for 2026 is to fly into Milan or Rome and then take a high-speed Frecciarossa train or a low-cost "puddle-jumper" flight to your final destination like Venice, Florence, or Naples, which are often significantly more expensive to fly into directly.