[Expired] [Award Alert] Fly to Italy for 55K Points in Business Class

Updated: May 20, 2026, 6:05am CDT

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Award Deal — Details
Best Ways To Book
Final Thoughts

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Update:

The offer mentioned below has expired and is no longer available.

Dreaming of Italy? Lucky for you, we have found wide-open availability to Milan in business class for as low as 55,000 points per person each way or 21,000 in economy. There’s also availability to Venice and Naples on some dates.

No matter which cabin you choose, booking with points and miles will save you a lot of money on flights, leaving you with more to spend on pasta and wine.

These flights may go quickly, so let’s take a look at the details.

Award Deal — Details

Flights to Europe — especially to Italy — can get pretty expensive, even in economy. If you’ve been thinking about booking a trip, now is a great time to lock in a deal.

Whether you’re planning a city escape, a longer European adventure, or a trip to Italy that’s been on your list for a while, this deal is worth a look.

While you’ll fly with American Airlines, you’ll book these flights through Alaska Airlines Atmos Rewards.

Class: Business
Routes: New York (JFK) and Philadelphia (PHL) to Milan (MXP), Naples (NAP), and Venice (VCE)
Airline: American Airlines
Program: Alaska Airlines Atmos Rewards
Cost: As low as 21,000 points (economy) and 55,000 points (business class) plus $18.10 in taxes and fees
Dates: May 2026 through February 2027
Seats: Up to 9 passengers in economy; up to 5 passengers in business

To search for available dates, you can use a tool like Seats.aero, which provides a big-picture overview of a range of dates and routes. Note that most availability is from JFK, with select dates from Philadelphia also available for 55,000 points.

Seats.aero USA Italy award May 2026 — Image Credit: Seats.aero

The cheapest way to book these business class flights is with the Alaska Airlines Atmos Rewards, which costs just 55,000 points one-way from East Coast cities.

For example, you can book this nonstop flight from New York (JFK) to Milan (MXP) for 55,000 points and just $18.10 in taxes and fees.

Screenshot — Image Credit: Alaska Airlines

While Alaska Atmos Rewards is the cheaper option for business-class redemptions, we’re finding that American’s AAdvantage program is currently the better deal for economy awards, with fares starting at 21,000 miles compared to 27,500 through Alaska.

Hot Tip:

This award alert is perfect for anyone planning a trip to Italy later this year or in the beginning of 2027, as there are up to 5 business class seats available — enough to bring the family or a group of friends along.

Best Ways To Book

The best way to book these business class awards is by redeeming Alaska Atmos Rewards points.

You can earn Alaska points by using an Alaska Airlines credit card, shopping through the Atmos Rewards shopping portal, dining at restaurants that participate in Atmos Rewards Dining, flying with Alaska’s Oneworld partners, and more. You also can transfer points from Bilt Rewards (1:1) or Marriott Bonvoy (3:1).

If you want to redeem AAdvantage miles, you can transfer Citi ThankYou Points and Bilt Rewards points at a 1:1 ratio to AA. Otherwise, you can transfer Marriott Bonvoy points at a less desirable 3:1 rate, or you purchase AAdvantage miles.

Final Thoughts

If you’ve been eyeing a trip to Italy and have the points ready to go, it’s not too late to lock in a high-value redemption for trips between now and February. Just don’t hesitate. Award space like this will be snapped up quickly, especially for peak holiday travel.