Italy flights are notoriously pricey, but a fresh sweet spot just opened up. American Airlines is releasing wide-open business class award space to Milan, Venice, and Naples, and you can book it through Alaska Mileage Plus for as little as 55,000 points one-way, plus $18.10 in taxes and fees.
The deal: American Airlines operates the flights from New York (JFK) and Philadelphia (PHL), but Alaska's Atmos Rewards program prices them lower than AAdvantage does for business class. Economy runs even cheaper through AAdvantage directly, starting at 21,000 miles. Seats are wide open, up to 9 in economy and 5 in business, for travel from May 2026 through February 2027. That means you can bring a partner, friends, or the whole family and still find seats together.
Most availability is out of JFK, though select Philadelphia dates are also priced at 55,000 points. A quick search on a tool like Seats.aero will show you the full spread of open dates so you can build your trip around the best fare, not the other way around.
How to book it: You'll need Alaska Mileage Plus points to lock in the business class rate. If you don't already have a stash, you can earn Alaska miles fast with the right card, or transfer in from partner programs. Marriott Bonvoy points convert at 3:1, which is steep, so it's really only worth it if you're sitting on a big Bonvoy balance with nowhere else to use it. A faster route: Bilt Rewards points transfer 1:1 to Alaska, so if you're already earning Bilt on rent, this is a clean way to put those points to work.
Prefer economy? Citi ThankYou Points transfer 1:1 to AAdvantage, making that 21,000-mile fare even easier to reach.
Why it matters: A round-trip business class seat to Italy can easily run $3,000 or more in cash. At 55,000 points each way, you're looking at roughly 110,000 points total for a seat that would otherwise blow your travel budget. Deals like this on wide-open dates don't last. If Italy has been on your list, this is the moment to check availability and lock in your trip before the seats disappear.
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