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The cheapest order to fly Lisbon, Porto and Madrid from Boston

There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about $813 a person and the most expensive at $892, a difference of $79 for visiting exactly the same places.

Fly them in this order

Boston → Lisbon → Madrid → Porto → Boston

About $813 per person in flights, based on fares recently seen on these routes.

Every order, priced

  1. Boston → Lisbon → Madrid → Porto → Boston$813
    cheapest order
  2. Boston → Lisbon → Porto → Madrid → Boston$817
    $4 more per person
  3. Boston → Madrid → Lisbon → Porto → Boston$829
    $16 more per person
  4. Boston → Madrid → Porto → Lisbon → Boston$855
    $42 more per person
  5. Boston → Porto → Lisbon → Madrid → Boston$872
    $59 more per person
  6. Boston → Porto → Madrid → Lisbon → Boston$892
    $79 more per person

The cheapest order, leg by leg

  1. Boston to Lisbon$337
  2. Lisbon to Madrid$31
  3. Madrid to Porto$23
  4. Porto to Boston$422
  • Out of Boston, the cheapest first flight goes to Madrid at about $326, but the cheapest order starts in Lisbon at $337 because the rest of the route is cheaper that way.
  • Going home, the cheapest flight leaves from Madrid at about $406, but the cheapest order ends in Porto at $422 because the rest of the route is cheaper that way.
  • The dearest order pays $455 for Lisbon to Boston, a flight the cheapest order never takes.
  • Porto to Boston is 52% of what the cheapest order spends on flights, so it is the leg to watch.

Between the cities

  • Lisbon to Madrid: about 500 km (310 miles) as the crow flies. Also by ground: ALSA / FlixBus (overnight), about 8h, usually $25 to $50.
  • Madrid to Porto: about 420 km (260 miles) as the crow flies. Also by ground: ALSA / FlixBus, about 9h, usually $30 to $65.

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 authorisation 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 $79 a person on this trip, 10% of what the cheapest way round costs. Of the 72 trips we price in full, that is number 68 for how much the order matters, one of the smaller gaps: on this trip your dates are likely to matter more than the order.

What these numbers are

Cached one-way fares, 12 of 12 legs priced from real observations, put together on October 29, 2026, from fares departing October 29, 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 2, 2027 to January 16, 2027, 14 days, for 2 travelers. Our dates, not yours, and about two minutes.

Plan Lisbon, Porto and Madrid from Boston nowOpen the form instead and pick your own dates

Signed out, 3 plans 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, legs are checked live, with 2 free trips you can change afterwards.