Stopovers between Chicago and Milan
Chicago to Milan is about 7,260 km. 12 cities sit close enough to the route to add a night or two, and Reykjavík, Madrid have airline stopover programs. Pick your dates to see what each one really costs.
Cities on the way
Sits almost exactly on the great circle between North America and Europe, so the detour is tiny.
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.
Heathrow Express gets you to Paddington in 15 minutes.
UP Express runs to Union Station in 25 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.
European feel without crossing the Atlantic.
Short train in; Bruges and Ghent are an easy day trip.
Plenty of flights from every airline make for flexible stopovers.
Iberia lets you stop 1–9 nights at no extra airfare.
Beer gardens, museums and easy Alpine day trips.