Good fares to Italy are pretty common from the northeast, but it’s always good news when other cities join in. United and her Star Alliance partners have some solid deals from major airports across the USA to several Italian cities, with Delta and American matching prices on at least one route to Rome. These deals are available on select days this fall, but become much more widely available in late winter and next spring. Planing ahead can really pay off.
- Rome: New York ($332), Boston ($420, matched by American), Philadelphia ($477 matched by Delta)), San Francisco ($489)
- Venice: Miami ($418), Chicago ($473)
- Florence: Miami ($419), New York ($439)
- Naples: Miami ($414)
- Milan: Philadelphia ($492)
Venice by Pixabay user jpeter2
These are basic economy fares, meaning a carry-on and meals are included but not seat selection or checked bags. Buying-up to main cabin varies in price by route, but is generally just over $100 round trip. These fares are generally available through either booking directly or with an online travel agency, but the New York to Rome price is only from United. When you find TAP fares (particularly prevalent with Miami & San Francisco) these may be a pair of one-way flights matched up, meaning you could potentially book a flight to Italy but home from somewhere else. If you’re looking for good options to other locations in Europe, that is also an option.
Sample Route
- Departure: Chicago O’Hare
- Stops: Montreal
- Arrival: Venice
How to Book
- Follow link for sample dates or search your favorite OTA / Google Flights for departure and destination
Travel Dates
- Fall 2019 through spring 2020, holidays excluded
- 6, 7, or 8 day stay required
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
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