When is the cheapest time to fly to Italy from the US?

November through March, excluding the Christmas fortnight, with late January and early February usually the floor. Summer fares from the US run two to three times winter fares on the same route. The shoulder months, May and September, sit in between and sell out early because they're the best value overall once you count weather. As a rule of thumb, book transatlantic flights around four to six months ahead for summer, and two to three for the off-season. Flying midweek and being flexible about which Italian airport you land at saves more than any booking trick.

This one changes. Last checked August 13, 2026 — confirm it close to your trip.