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The cheapest order to fly Paris, Milan and Rome from Boston

There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about $846 a person and the most expensive at $1,343, a difference of $497 for visiting exactly the same places.

Fly them in this order

Boston → Rome → Milan → Paris → Boston

About $846 per person in flights, based on fares recently seen on these routes.

Every order, priced

  1. Boston → Rome → Milan → Paris → Boston$846
    cheapest order
  2. Boston → Milan → Rome → Paris → Boston$986
    $140 more per person
  3. Boston → Paris → Milan → Rome → Boston$1,181
    $335 more per person
  4. Boston → Paris → Rome → Milan → Boston$1,323
    $477 more per person
  5. Boston → Rome → Paris → Milan → Boston$1,333
    $487 more per person
  6. Boston → Milan → Paris → Rome → Boston$1,343
    $497 more per person

Why end in Paris

  1. Boston to Rome$335
  2. Rome to Milan$40
  3. Milan to Paris$21
  4. Paris to Boston$450
  • Out of Boston, the cheapest first flight goes to Paris at about $303, but the cheapest order starts in Rome at $335 because the rest of the route is cheaper that way.
  • Going home, Paris is the cheapest city to leave from at about $450, against $937 from Milan.
  • The dearest order pays $816 for Rome to Boston, a flight the cheapest order never takes.
  • Paris to Boston is 53% of what the cheapest order spends on flights, so it is the leg to watch.

Between the cities

  • Rome to Milan: about 480 km (300 miles) as the crow flies. Also by ground: Frecciarossa / Italo, about 3h 10m, usually $30 to $90. Or FlixBus (overnight), about 8h, usually $15 to $35.
  • Milan to Paris: about 640 km (400 miles) as the crow flies. Also by ground: TGV INOUI Milan to Paris (via Turin), about 7h, usually $40 to $130. Or FlixBus (overnight), about 11h, usually $30 to $60.

Entry rules on a US passport

  • US passport: visa-free in the Schengen area for 90 days in any 180. The Entry/Exit System registers biometrics at the border, and the ETIAS pre-travel authorization may now be required; check the official site. Official source

Rules change; check the official source for your passport and dates before you book.

How much the order matters here

Getting the order right is worth $497 a person on this trip, 59% of what the cheapest way round costs. Of the 107 trips we price in full, that is number 9 for how much the order matters, one of the trips where it matters most: flying these cities in the wrong order is an expensive mistake.

The same cities from other airports

The cheapest order depends on where you start. From Boston it starts in Rome.

  • From Torontostart in Rome, about $685 a person, $74 less than the dearest order
  • From Chicagostart in Rome, about $758 a person, $581 less than the dearest order

What these numbers are

Cached one-way fares, 12 of 12 legs priced from real observations, put together on September 24, 2026, from fares departing September 25, 2026 onwards. Right for comparing one order with another, not a quote for your dates.

A plan prices your own dates and weighs hours as well as fares, so it can pick a different order from this page.

Other trips priced this way

From Boston

Trips through the same cities

Put dates on it

Same cities on real dates, plus what one search cannot show: layovers long enough to count as a free city, two tickets that beat one, and cheaper days either side. No account and no card.

One press starts it on January 16, 2027 to January 30, 2027, 14 days, for 2 travelers. Our dates, not yours, and about two minutes.

Plan Paris, Milan and Rome from Boston nowOpen the form instead and pick your own dates

Signed out, 3 trips a day per address, priced from cached fares and the free sources, so some legs may be estimates and the plan says which. Signed in, your first trip also searches Google Flights live, and you can change your trips afterwards.