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The cheapest order to fly Madrid, Lisbon and Rome from San Francisco

There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about $705 a person and the most expensive at $1,293, a difference of $588 for visiting exactly the same places.

Fly them in this order

San Francisco → Lisbon → Madrid → Rome → San Francisco

About $705 per person in flights, based on fares recently seen on these routes.

Every order, priced

  1. San Francisco → Lisbon → Madrid → Rome → San Francisco$705
    cheapest order
  2. San Francisco → Madrid → Lisbon → Rome → San Francisco$832
    $127 more per person
  3. San Francisco → Lisbon → Rome → Madrid → San Francisco$874
    $169 more per person
  4. San Francisco → Madrid → Rome → Lisbon → San Francisco$1,093
    $388 more per person
  5. San Francisco → Rome → Lisbon → Madrid → San Francisco$1,187
    $482 more per person
  6. San Francisco → Rome → Madrid → Lisbon → San Francisco$1,293
    $588 more per person

Why Lisbon first

  1. San Francisco to Lisbon$289
  2. Lisbon to Madrid$31
  3. Madrid to Rome$28
  4. Rome to San Francisco$357
  • Out of San Francisco, Lisbon is the cheapest first stop at about $289. Rome would be $607.
  • Going home, Rome is the cheapest city to leave from at about $357, against $623 from Lisbon.
  • The dearest order pays $623 for Lisbon to San Francisco, a flight the cheapest order never takes.
  • Rome to San Francisco is 51% 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 Rome: about 1,360 km (840 miles) as the crow flies. No train or bus we would suggest instead of flying.

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 $588 a person on this trip, 83% of what the cheapest way round costs. Of the 72 trips we price in full, that is number 2 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 San Francisco it starts in Lisbon.

  • From Miamistart in Rome, about $711 a person, $133 less than the dearest 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 November 1, 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 San Francisco

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.

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