Stopovers between Chicago and Rome
Chicago to Rome is about 7,742 km. 12 cities sit close enough to the route to add a night or two, and Zurich, Geneva, Reykjavík have airline stopover programs. Pick your dates to see what each one really costs.
Cities on the way
Train from the airport to the old town in 12 minutes, so even a single night works.
Compact lakeside city with free public transport for hotel guests.
Sits almost exactly on the great circle between North America and Europe, so the detour is tiny.
Iberia lets you stop 1–9 nights at no extra airfare.
RER B from CDG reaches central Paris in about 35 minutes.
US preclearance on the way home means you land in the US as a domestic arrival.
UP Express runs to Union Station in 25 minutes.
Heathrow Express gets you to Paddington in 15 minutes.
Train from Schiphol to Centraal in 15 minutes, every few minutes.
S-Bahn reaches the centre in 15 minutes; the Rhine valley is close.
Beach, Gaudí and late dinners.
One of the easiest stopover cities in Europe: metro from the airport, walkable, great food.