The cheapest order to fly Rome, Athens and Istanbul from Chicago
There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about $919 a person and the most expensive at $1,059, a difference of $140 for visiting exactly the same places.
Fly them in this order
Chicago → Istanbul → Athens → Rome → Chicago
About $919 per person in flights, based on fares recently seen on these routes.
Every order, priced
- Chicago → Istanbul → Athens → Rome → Chicago$919cheapest order
- Chicago → Rome → Athens → Istanbul → Chicago$940$21 more per person
- Chicago → Rome → Istanbul → Athens → Chicago$1,005$86 more per person
- Chicago → Istanbul → Rome → Athens → Chicago$1,008$89 more per person
- Chicago → Athens → Istanbul → Rome → Chicago$1,057$138 more per person
- Chicago → Athens → Rome → Istanbul → Chicago$1,059$140 more per person
Why end in Rome
- Chicago to Istanbul$384
- Istanbul to Athens$42
- Athens to Rome$37
- Rome to Chicago$456
- Out of Chicago, the cheapest first flight goes to Rome at about $372, but the cheapest order starts in Istanbul at $384 because the rest of the route is cheaper that way.
- Going home, Rome is the cheapest city to leave from at about $456, against $508 from Athens.
- Istanbul to Athens is about $42, but the other way round is $57. Same two cities, $15 apart on direction alone.
- Rome to Chicago is 50% of what the cheapest order spends on flights, so it is the leg to watch.
Between the cities
- Istanbul to Athens: about 560 km (350 miles) as the crow flies. No train or bus we would suggest instead of flying.
- Athens to Rome: about 1,050 km (650 miles) as the crow flies. No train or bus we would suggest instead of flying.
Entry rules on a US passport
- US passport: visa-free in Türkiye for up to 90 days in any 180. No e-Visa since December 2023, so you can leave the airport on a layover. Official source
- 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 $140 a person on this trip, 15% of what the cheapest way round costs. Of the 107 trips we price in full, that is number 81 for how much the order matters, one of the smaller gaps: on this trip your dates are likely to matter more than the order.
The same cities from other airports
The cheapest order depends on where you start. From Chicago it starts in Istanbul.
- From New Yorkstart in Athens, about $677 a person, $263 less than the dearest order
- From Torontostart in Rome, about $790 a person, $64 less than the dearest order
- From Miamistart in Rome, about $827 a person, $502 less than the dearest order
- From Bostonstart in Rome, about $888 a person, $467 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 16, 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.
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 Rome, Athens and Istanbul from Chicago nowOpen the form instead and pick your own datesSigned 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.