Stopovers between Chicago and Madrid
Chicago to Madrid is about 6,744 km. 12 cities sit close enough to the route to add a night or two, and Lisbon, Porto, Reykjavík 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.
Riverside wine town with a direct metro from the airport.
UP Express runs to Union Station in 25 minutes.
Plenty of flights from every airline make for flexible stopovers.
European feel without crossing the Atlantic.
One of the closest major airports to its downtown in the US.
Free Smithsonian museums; the metro goes from National to the Mall.
Sits almost exactly on the great circle between North America and Europe, so the detour is tiny.
US preclearance on the way home means you land in the US as a domestic arrival.
Andalusian charm; best outside the summer heat.
Beach, Gaudí and late dinners.
Heathrow Express gets you to Paddington in 15 minutes.