Flights from Chicago to Italy for a week

A week is Rome and one other place: Florence by train, Naples and the Amalfi Coast, or Venice. Fly into Rome or Milan with the better fare and home from the other.

Nonstop from Chicago: Rome (9h 05m), Milan (United · 8h 40m) and Naples (American · 9h 35m). One stop via Istanbul: Venice, Bologna, Catania, Palermo and Bari; via Zurich: Florence.

Axel's pick: Rome, nonstop and the lowest fare saved for these dates, $596.

Where to fly from Chicago to Italy for a week: round trips of 6 to 8 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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The cheapest matching round trip we’ve seen recently for each destination.

Cheapest right now: Rome $596 · Venice $601 · Bologna $606

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Flights from Chicago

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Italy for a week from other cities

Fares observed October 22 – 28, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Chicago

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 trattoriasNonstop · 9h 05m$596 (airline $628)Jan 12–19, 2027Check prices
Milan (MXP)Milan's fashion, the Duomo and trains to the lakesNonstop · United · 8h 40m$661 (airline $698)Jan 12–19, 2027Check prices
Venice (VCE)Venice's canals and islands1 stop via Istanbul$601 (airline $635)Nov 10–17, 2026Check prices
Naples (NAP)Naples, pizza and the gateway to Pompeii and the Amalfi CoastNonstop · American · 9h 35m$659 (airline $694)Jan 12–19, 2027Check prices
Florence (FLR)Florence's Duomo, Uffizi and the Tuscan hills1 stop via Zurich$711 (airline $748)Dec 8–15, 2026Check prices
Bologna (BLQ)Bologna's food and a fast train to Florence and Venice1 stop via Istanbul$606 (airline $638)Nov 10–17, 2026Check prices
Catania (CTA)Catania, Mount Etna and Sicily's east coast1 stop via Istanbul$643 (airline $680)Dec 8–15, 2026Check prices
Palermo (PMO)Palermo's markets and Sicily's west1 stop via Istanbul$881 (airline $930)Jan 12–19, 2027Check prices
Bari (BRI)Bari, the gateway to Puglia's coast and trulli1 stop via Istanbul$1,212 (airline $1,276)Nov 10–17, 2026Check prices

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 Chicago to Italy for a week. Round-trip fares from Chicago to Italy for a week: Rome, Milan, Venice, Naples, Florence and Bologna and more, for stays of 6 to 8 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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