Flights from Chicago to Italy for Christmas

Christmas in Italy is nativity scenes, markets in the north and midnight mass in Rome, with cold clear days and short lines at the museums. Fares peak from December 19 to January 3; the week before is the value.

Nonstop from Chicago: Rome (United, American, ITA Airways), Milan (United) and Naples (American). One stop via Brussels: Bologna. No nonstop seen to Venice, Florence, Catania, Palermo and Bari on the dates searched recently.

Axel's pick: Rome, nonstop on United, American and ITA Airways and the lowest fare saved for these dates, $1,275.

Where to fly from Chicago to Italy for Christmas: fares for Christmas week 2026 (Dec 19 to 26) and New Year's week (Dec 26 to Jan 2) 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 Christmas week 2026 (Dec 19 – Dec 26, 2026) and New Year's week (Dec 26 – Jan 2, 2027).

Cheapest right now: Rome $1,275 · Milan $1,288 · Bologna $1,683

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Flights from Chicago

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Italy for Christmas from other cities

Fares observed October 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 · United, American, ITA Airways$1,275 (airline $1,343)Dec 19–26, 2026Check prices
Milan (MXP)Milan's fashion, the Duomo and trains to the lakesNonstop · United$1,288 (airline $1,363)Dec 19–26, 2026Check prices
Venice (VCE)Venice's canals and islandsNo nonstop seenNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Naples (NAP)Naples, pizza and the gateway to Pompeii and the Amalfi CoastNonstop · AmericanNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Florence (FLR)Florence's Duomo, Uffizi and the Tuscan hillsNo nonstop seenNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Bologna (BLQ)Bologna's food and a fast train to Florence and Venice1 stop via Brussels$1,683 (airline $1,778)Dec 19–26, 2026Check prices
Catania (CTA)Catania, Mount Etna and Sicily's east coastNo nonstop seenNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Palermo (PMO)Palermo's markets and Sicily's westNo nonstop seenNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Bari (BRI)Bari, the gateway to Puglia's coast and trulliNo nonstop seenNo matching fare savedDec 19 – Dec 26, 2026 (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.

About these places

Facts checked October 27, 2026. Sources: OPM: federal holidays 2026 and 2027

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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 Christmas. Round-trip fares from Chicago to Italy for Christmas: Rome, Milan, Venice, Naples, Florence and Bologna and more, priced for Christmas week 2026 (Dec 19 to 26) and New Year's week (Dec 26 to Jan 2). 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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