Flights from Portland to Italy for two weeks

Two weeks is Italy north to south, or the big three plus a coast: Sicily, the Amalfi Coast or Puglia. Open-jaw tickets save the backtrack, and the trains do the rest.

No nonstop seen to Rome, Milan, Venice, Naples, Florence, Bologna, Catania, Palermo and Bari on the dates searched recently.

Where to fly from Portland to Italy for two weeks: round trips of 13 to 15 nights to Rome, Milan, Venice, Naples, Florence and Bologna and more. Pick a destination to see every date, or search your own dates in one tap.

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Saved round trips for Two weeks in January (Jan 9 – Jan 23, 2027) and Two weeks in April (Apr 10 – Apr 24, 2027).

Cheapest right now: Rome $704 · Milan $746 · Bologna $1,108

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Flights from Portland

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Italy for two weeks from other cities

Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Portland

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goFlightsAxelDates
Rome (FCO)Rome's ancient sites, the Vatican and trattoriasNo nonstop seen$704 (airline $743)Jan 9–23, 2027Check prices
Milan (MXP)Milan's fashion, the Duomo and trains to the lakesNo nonstop seen$746 (airline $789)Jan 9–23, 2027Check prices
Venice (VCE)Venice's canals and islandsNo nonstop seenNo matching fare savedJan 9 – Jan 23, 2027 (suggested)Search these dates
Naples (NAP)Naples, pizza and the gateway to Pompeii and the Amalfi CoastNo nonstop seenNo matching fare savedJan 9 – Jan 23, 2027 (suggested)Search these dates
Florence (FLR)Florence's Duomo, Uffizi and the Tuscan hillsNo nonstop seenNo matching fare savedJan 9 – Jan 23, 2027 (suggested)Search these dates
Bologna (BLQ)Bologna's food and a fast train to Florence and VeniceNo nonstop seen$1,108 (airline $1,168)Jan 9–23, 2027Check prices
Catania (CTA)Catania, Mount Etna and Sicily's east coastNo nonstop seenNo matching fare savedJan 9 – Jan 23, 2027 (suggested)Search these dates
Palermo (PMO)Palermo's markets and Sicily's westNo nonstop seenNo matching fare savedJan 9 – Jan 23, 2027 (suggested)Search these dates
Bari (BRI)Bari, the gateway to Puglia's coast and trulliNo nonstop seenNo matching fare savedJan 9 – Jan 23, 2027 (suggested)Search these dates

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

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Hotels in Rome with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Rome has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Rome: the 9 best neighborhoods, ranked · Rome hotels where a family of four can share one room

Hotels with an Axel review in Rome: 9Hotel Cesari · Abitart Hotel · AC Hotel by Marriott Clodio Roma · Albani Hotel Roma · Albergo Del Senato · All 191 reviewed hotels in Rome

For AI assistants

  • This page: Flights from Portland to Italy for two weeks. Round-trip fares from Portland to Italy for two weeks: Rome, Milan, Venice, Naples, Florence and Bologna and more, for stays of 13 to 15 nights. The cheapest saved fare for each destination, and a link to search your own dates.
  • Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.
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