Travel to Italy with flights for less than $550 round-trip

Flight deals to Europe are going fast, which makes round-trip flights priced around $500 to Milan, Rome, Venice, Florence and Bologna, Italy, a deal you won't want to miss.

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Deal basics

Airlines: TAP Air Portugal.
Routes: New York; Newark; Chicago; Washington, D.C.; San Francisco; San Jose, California; and others to Rome, Venice, Bologna, Milan and Florence.
How to book: Directly through the airline.
Travel dates: May/September 2022-February 2023 for flights to Milan; October 2022-February 2023 for flights to Rome; May 2022/September-October 2022 for flights to Venice; September-November 2022/January-February 2023 for flights to Florence; May 2022/August-October 2022 for flights to Bologna.
Book by: One to two days.

Shoutout to Scott’s Cheap Flights for sending us this deal. Sign up for a Premium membership, which users can try for free for 14 days or $49 per year, and get deals up to 90% off. You can also upgrade to the Elite tier for $199 per year and receive all the Premium deals plus premium economy, business-class and first-class alerts.

Sample flights

Travelers can depart from a smattering of U.S. origin points to Italy for this deal, ranging in price from $445 to $550 total. Example round-trip routes include:

• New York City to Milan and Newark/Chicago to Rome, starting at $445.
• Washington, D.C., to Venice, starting at $455.
• Chicago/San Francisco to Bologna, starting at $456.
• Newark/New York City to Venice, starting at $462 and $476 respectively.
• Newark/San Francisco/Chicago to Milan, starting at $463.
• Washington, D.C., to Milan, starting at $474.
• Newark/New York City to Florence, starting at $523 and $548 respectively.
• San Jose to Rome, starting at $527.

Read more: 8 underrated destinations in Italy you need to visit

Because this deal includes flights to five Italian cities, it's easiest to comb through this deal by starting with Google Flights and entering your origin city and desired destination.

On Google Flights, you'll notice the option to book flights for a slightly lesser price via a third party, but we recommend booking through the airline directly for flexibility in dealing with potential flight changes or issues down the line.

In this case, head to TAP Air Portugal to book these flights directly. From there, you'll be asked to choose from one of four economy fare types.

The advertised flights in this deal are for the most restrictive fare in TAP’s economy class, which means tickets are nonrefundable but can be changed for a hefty $300. Additionally, this fare type does not include checked luggage, so consider paying $65 to upgrade to TAP’s basic economy fare if you plan on checking a bag.

Read more: 9 tips for beginners visiting Italy for the first time

With TAP specifically, it's cheaper to upgrade your fare type at the time of booking rather than retroactively add checked baggage, the price of which increases with each fare type. For example, TAP charges you $95 to add one checked bag to discount fares and $124 to check more than one bag to basic fares.

This discount fare-type flight costs $572. Alternatively, you could pay $700 for a basic economy fare on the same flight, which would include one checked bag for free.

Maximize your purchase

Don’t forget to use a card that earns bonus points on airfare purchases, such as The Platinum Card® from American Express (5 points per dollar on airfare booked directly with the airline or through American Express Travel, on up to $500,000 on these purchases per calendar year), Citi Prestige® Card (5 points per dollar on airfare), Citi Premier® Card, Chase Sapphire Reserve (3 points per dollar on airfare), American Express® Gold Card (3 points per dollar on airfare when booked directly with the airline or through Amex Travel) or the Chase Sapphire Preferred Card (2 points per dollar on travel). Check out this post for more on maximizing airfare purchases.

The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Related: Daydreaming of moving to Italy? Another village near Rome is selling homes for 1 euro

Bottom line

Although this deal won't last, be sure to double-check the particulars of each fare type before booking to verify it meets your needs regarding luggage.