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The cheapest order to fly Paris, Milan and Rome from Chicago

There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about $816 a person and the most expensive at $1,039, a difference of $223 for visiting exactly the same places.

Fly them in this order

Chicago → Paris → Milan → Rome → Chicago

About $816 per person in flights, based on fares recently seen on these routes.

Every order, priced

  1. Chicago → Paris → Milan → Rome → Chicago$816
    cheapest order
  2. Chicago → Paris → Rome → Milan → Chicago$889
    $73 more per person
  3. Chicago → Rome → Milan → Paris → Chicago$912
    $96 more per person
  4. Chicago → Rome → Paris → Milan → Chicago$947
    $131 more per person
  5. Chicago → Milan → Paris → Rome → Chicago$1,009
    $193 more per person
  6. Chicago → Milan → Rome → Paris → Chicago$1,039
    $223 more per person

Why Paris first

  1. Chicago to Paris$294
  2. Paris to Milan$27
  3. Milan to Rome$39
  4. Rome to Chicago$456
  • Out of Chicago, Paris is the cheapest first stop at about $294. Milan would be $493.
  • Going home, Rome is the cheapest city to leave from at about $456, against $517 from Milan.
  • The dearest order pays $493 for Chicago to Milan, a flight the cheapest order never takes.
  • Rome to Chicago is 56% of what the cheapest order spends on flights, so it is the leg to watch.

Between the cities

  • Paris to Milan: about 640 km (400 miles) as the crow flies. Also by ground: TGV INOUI Paris to Milan (via Turin), about 7h, usually $40 to $130. Or FlixBus (overnight), about 11h, usually $30 to $60.
  • Milan to Rome: about 480 km (300 miles) as the crow flies. Also by ground: Frecciarossa / Italo, about 3h 10m, usually $30 to $90. Or FlixBus (overnight), about 8h, usually $15 to $35.

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 authorization 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 $223 a person on this trip, 27% of what the cheapest way round costs. Of the 107 trips we price in full, that is number 36 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 Chicago it starts in Paris.

  • From Torontostart in Rome, about $685 a person, $74 less than the dearest order
  • From Bostonstart in Rome, about $846 a person, $497 less than the dearest order

What these numbers are

Cached one-way fares, 12 of 12 legs priced from real observations, put together on November 12, 2026, from fares departing November 12, 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 Chicago

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 16, 2027 to January 30, 2027, 14 days, for 2 travelers. Our dates, not yours, and about two minutes.

Plan Paris, Milan and Rome from Chicago nowOpen the form instead and pick your own dates

Signed out, 3 trips a day per address, priced from cached fares and the free sources, so some legs may be estimates and the plan says which. Signed in, your first trip also searches Google Flights live, and you can change your trips afterwards.