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Earlier today I posted some good deals with Oneworld airlines to Switzerland. A little further digging found excellent fares to Italy as well, including main cabin fares for less than $350. These are for major destinations (Rome, Venice, and Milan) from Oneworld again, though Star Alliance has matched pricing on one route noted below. The travel window is from September through next Spring, meaning you can go during winter break or when the weather is warmer. Christmas and New Year’s travel are available for at these prices (or just slightly more) for several of these routes. But I would be a little careful on choosing dates to Venice in the fall to avoid flooding season.
- Milan: from New York $236+, $320 main cabin; Boston $351+ main cabin
- Rome: from New York $356+ Air Canada, $362 AA; Boston $337+ main cabin
- Venice: from Boston $347 main cabin
Venice by Pixabay user jpeter2
Those deals are great for cash prices. However, if you want to use Chase Ultimate Rewards points and have the Sapphire Reserve, you can book the main cabin deals for just over 21,000 points. That’s a fraction of standard airline miles award pricing.
You *don’t* have to pay for seat choice, actually
Interestingly, the deals are only basic economy from New York to Milan and Rome, and the main cabin prices are outstanding. That means you’re getting seat selection and a checked bag at basic economy prices. So feel confident that you can book your entire family to Italy for cheap and still sit together. These prices are available both directly from the airlines as well as OTAs; in some cases fares are repricing lower than noted on Google Flights so look closely. OTAs may say that the main cabin fares include a seat selection fee, but that it only for Main Cabin Extra and seats near the front of the plane.
These are great prices so book now for an Italian vacation with your family at rock bottom prices.
(SEE ALSO: The 8 Most Romantic Cities in the World)
Sample Route
- Departure: New York JFK
- Stops: None
- Arrival: Milan
How to Book
- Follow link for sample dates or search your favorite OTA / Google Flights for departure and destination
Travel Dates
- Late September 2019 through March 2020
- 7 day stay required
Where to Stay in Italy
- Hilton Garden Inn Rome Claridge
- Crown Plaza Rome St. Peter’s
- Marriott Milan Hotel
- Holiday Inn Milan – Garibaldi Station
- AC Hotel Venezia
- Hilton Molino Stucky Venice
Things to Do in Italy
- Colosseum – see also Dan’s pro-tip for visiting Ancient Rome sites
- Roman Forum
- Trevi Fountain
- Duomo di Milano
- Galleria Vittorio Emanuele II in Milan
- Milan’s Castello Sforzesco
- The Doge’s Palace in Venice
- Venice’s Canal Grande
Good luck and happy flying!
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
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