Stopovers between Chicago and Nairobi
Chicago to Nairobi is about 12,910 km. 12 cities sit close enough to the route to add a night or two, and Lisbon, Madrid, Zurich have airline stopover programs. Pick your dates to see what each one really costs.
Cities on the way
One of the easiest stopover cities in Europe: metro from the airport, walkable, great food.
Iberia lets you stop 1–9 nights at no extra airfare.
Train from the airport to the old town in 12 minutes, so even a single night works.
Riverside wine town with a direct metro from the airport.
UP Express runs to Union Station in 25 minutes.
Sits almost exactly on the great circle between North America and Europe, so the detour is tiny.
Beach, Gaudí and late dinners.
Compact lakeside city with free public transport for hotel guests.
Plenty of flights from every airline make for flexible stopovers.
Turkish Airlines may give you a free hotel night if you connect here for 20+ hours.
The Leonardo Express train reaches Termini in 32 minutes.
RER B from CDG reaches central Paris in about 35 minutes.