Planning your trip to Italy? Whether you’re a less-experienced traveler or a seasoned veteran, we’ve gathered simple, stress-free tips to help you find affordable flights from the U.S. or Canada.

Quick Summary (TLDR)

  1. Start searching early, but set alerts and watch prices — don’t panic-book the first “decent” fare… 6-8 months before departure is generally the best time to start looking at international flights to Italy during peak summer season (i.e., October - January for June/July departure). Flights to Europe are often cheapest about 3-6 months ahead of travel.

    • November - January: Airlines may open inventory for next summer and early deals can appear (especially if they run promotions). Great time to start watching prices.

    • Late January – February: More fares for late June start to price in, and this can be a good period to lock in a competitive fare.

    • February – March: Many of the best “base” fares appear; reviewing prices weekly and using alerts is effective.

    • Early April – Mid-April: This is about 10–12 weeks ahead of late June/early July—commonly recommended as a “final buy” window before prices climb into peak demand.

  2. Use at least two meta-search tools (Google Flights + a European-friendly search like Skyscanner or Expedia, Momondo, etc.) and compare

  3. Be flexible on dates, airports, and routing (open-jaw/multi-city flights often save money)

  4. Beware low-cost carriers: Fares are cheap, but add-on fees (baggage, seat selection, meals) quickly erase savings

** Pro Tip: As we head into the holiday season, bear in mind that you can score great deals and discounts on international flights on Black Friday (11/28/25) and/or Travel Tuesday (12/2/25)! We highly suggest setting a reminder to look and book on these days. It’s becoming more common for carriers to offer these deals throughout this entire week — but be sure to act fast!

How to Track Prices on Google Flights

Step 1 — Go to Google Flights
Visit google.com/flights.

Step 2 — Enter your trip details

  • Departure city (e.g., Chicago, New York, Toronto)

  • Destination city (e.g., Rome, Milan)

  • Travel dates

Step 3 — View the calendar

  • Click on the date field.

  • A calendar will appear with prices on each day.

  • Use this to spot cheaper dates.

Step 4 — Turn on “Track Prices”

  • Once your route is entered, look for the toggle button that says “Track prices.”

  • Turn it on. (You’ll need to be logged into a Google account.)

Step 5 — Get notifications

  • Google will automatically email you when prices for your trip drop or rise.

  • You can track multiple routes (e.g., New York → Rome and New York → Milan).