[Expired] Award Alert: Summer Availability to Italy from 55K in Business

Updated: June 13, 2025, 2:39am 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.

Despite what you’re told, it’s not too late to book that trip to Italy (or elsewhere in Europe!) this summer.

The team at Upgraded Points just found availability on several routes from the U.S. during peak summer travel — here’s how you can book.

Award Deal — Details

Flights to Europe — especially to Italy — are notoriously expensive during the summer. You can expect to pay north of $2,000 for flights, and most likely, you’ll be sitting back in economy!

Instead, consider redeeming points and miles with this great award deal we found. There’s plenty of availability to Rome this summer from the East Coast and Midwest:

Class: Economy and business
Routes: Chicago (ORD) and New York (JFK) to Rome (FCO)
Airline: American Airlines
Cost: As low as 27,500 points (economy) and 55,000 points (business class) and $18 in taxes & fees
Dates: August 2025
Seats: Up to 9 passengers in economy; up to 6 passengers in business

The cheapest possible way to book these flights is through Alaska Airlines Mileage Plan. This program has business class flights for 55,000 miles one-way from New York (JFK) and Chicago (ORD).

For example, you can book this nonstop flight from Chicago to Rome (FCO) for 27,500 miles and just $18.10 in taxes and fees. If you prefer to fly in a bit more comfort than economy, you can also book business class flights to Italy for just 55,000 Alaska miles.

Alaska AA J award Rome — Image Credit: Alaska Airlines

If you have a large stash of American Airlines miles and prefer to book through American’s AAdvantage program, you can snag the same flight for 27,000 miles in economy plus $5.60. However, business class redemptions are pricier than Alaska’s for the same flight, starting at 70,000 AA miles.

AA awards to Rome — Image Credit: American Airlines

Hot Tip:

This award alert is perfect for anyone planning a trip to Italy in August 2025, with up to 6 business class seats available — enough to bring the whole family along.

Best Ways To Book

The best way to book these business class awards is by redeeming Alaska Mileage Plan miles.

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

Lastly, you can now transfer American Express Membership Rewards to Hawaiian Airlines at a 1:1 ratio, and then transfer from Hawaiian to Alaska.

If you want to redeem AAdvantage miles, remember that you can transfer Bilt Rewards points at a 1:1 ratio. Otherwise, you can transfer Marriott Bonvoy points at a less desirable 3:1 rate, or purchase AAdvantage miles with up to a 40% bonus.

Final Thoughts

If you’ve been eyeing a trip to Italy this summer and have the miles ready to go, this is a golden opportunity to lock in a high-value redemption for your summer getaway. Just don’t hesitate — award space like this is snapped up quickly, especially for peak summer travel.