(source: mentalfloss.com)
The former is Chernobyl. In 1986, the city was the centre of the worst civil nuclear disaster in human history. Today, it lies abandoned, the stronghold of cockroaches.
The latter is Chichen Itza, Mexico. It was built between 750 and 900 AD by the Itza people, and lay abandoned for a millenium before it was designated a World Heritage site in 1988. It's had minimal restorative work done to it - the major work done there is clearance of the surrounding site, rather than restoration of the pyramid itself.
Which of those two sites has held up better? I'd say it's the latter. Conveniently, that's also the closest parallel to your medieval city. It's also in a tropical climate (hotter and worse for preservation of buildings than you specified). If it can hold out a millenium, that gives you a fair idea of how a medieval city could last, if it was built well.