Stopovers between Chicago and Johannesburg
Chicago to Johannesburg is about 14,019 km. 12 cities sit close enough to the route to add a night or two, and Lisbon, Madrid, Porto have airline stopover programs. Pick your dates to see what each one really costs.
Cities on the way
Plenty of flights from every airline make for flexible stopovers.
UP Express runs to Union Station in 25 minutes.
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.
Free Smithsonian museums; the metro goes from National to the Mall.
One of the closest major airports to its downtown in the US.
European feel without crossing the Atlantic.
Riverside wine town with a direct metro from the airport.
Gateway to Latin America with a beach on the way.
Royal Air Maroc's hub; Marrakech is a train ride away.
Train from the airport to the old town in 12 minutes, so even a single night works.
Beach, Gaudí and late dinners.