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)
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)
Use at least two meta-search tools (Google Flights + a European-friendly search like Skyscanner or Expedia, Momondo, etc.) and compare
Be flexible on dates, airports, and routing (open-jaw/multi-city flights often save money)
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!
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Start with Google Flights for a clean calendar view and exploration map. It’s fast for spotting date/airport combos
Then cross-check with Skyscanner and Momondo — they often show different aggregators or consolidator fares that can be cheaper. Set price alerts on at least one of these.
Use Hopper if you want push notifications and a “wait vs buy” recommendation (useful but not perfect)
TIP: open an extra browser window with an “explore” search (multi-month view) to find cheapest travel weeks
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Avoid last-minute summer bookings if you want lower prices — supply/demand spikes in July.
For travel to Europe, industry guidance suggests starting to track fares several months out and commonly booking around 45–60 days before departure for the lowest fares on many routes, though windows can vary by season and route. Summer is peak travel season (especially foreign tourism within Italy). Don’t wait until the last minute if you want to avoid high fares and limited availability. Use price alerts so you can act if fares drop.
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Set alerts on Google Flights, Skyscanner, or Momondo for your preferred routes. You’ll get emails when prices change. Don’t rely on a single day of low prices, unless cost decreases drastically; look for a stable dip.
Use the price graph and “track” functions so you can buy when a meaningful drop happens. If you see a flash sale, act fast — sales can evaporate in hours.
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Be flexible by a few days. Flying mid-week or adding/subtracting 1–2 days can drop price dramatically. Use the calendar view on Google Flights/Skyscanner. We recommend getting in a few days early to beat the jet lag anyway!
Consider alternate arrival airports. Other airports within Italy or even other surrounding countries can be cheaper depending on routing — then take a cheap regional flight or train to your final spot.
Open-jaw / multi-city: Fly into one city and out of another (e.g., arrive Milan, depart Venice) — often cheaper and convenient for multi-stop travel.
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Book round-trip on the same carrier alliance when possible for protection/recourse.
If you mix separate tickets (e.g., transatlantic with a big carrier + separate intra-Europe low-cost), leave generous connection time or plan to overnight. You’ll be responsible for missed connections on separate tickets.
Open-jaw (arrive A, depart B) can cut costs and eliminate backtracking.
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If you (or guests) have travel credit cards that earn airline miles or offer companion/statement credits, compare using cash vs points. Sometimes using miles + taxes equals an unbeatable deal.
Consider transferable travel points (e.g., Amex, Chase) if you want the flexibility to move between airline partners.
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Pros: Very cheap base fares within Europe (Ryanair, easyJet, Wizz Air, others). Good for short hops.
Cons: Strict baggage limits, many add-on fees (seat selection, priority boarding, printed boarding passes), and sometimes remote airports. Add all fees to the base fare before deciding. If your itinerary includes an intercontinental carrier and separate LCC legs, beware. Separate tickets give no protection if one flight is delayed.
Packing hack: If possible, travel carry-on only to avoid checked-bag fees (measure/check size rules carefully — especially EU standard sizing).
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If multiple guests are traveling together, ask airlines about group fares — for 10+ travelers many airlines offer group rates and flexible payment options. (For smaller groups, compare prices individually.)
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Given uncertainty, check fare rules: is the ticket changeable/refundable? A slightly more expensive refundable/ticket-with-credit can be worth it for peace of mind.
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Use hidden-city and throwaway ticketing with caution: It’s risky and may violate airline rules; avoid unless you fully understand consequences.
Look for “error fares” / mistake fares on sites and mailing lists (e.g., Scott’s Cheap Flights, Dollar Flight Club) — they can be huge wins but require quick action. (If you rely on an error fare, be aware airlines sometimes cancel.)
Mix-and-match airports + separate one-way tickets can sometimes beat round-trip prices, but weigh risk/complexity (especially with LCC legs).
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).