The Plaza Mayor of Chinchón is considered one of the most beautiful in the world. A meeting place where livestock fairs were held, the town council purchased some houses in 1499 to hold its meetings, establishing the Town Hall in the same location where it stands today.

In 1502, Joanna the Mad and Philip the Handsome visited Chinchón and its Plaza Mayor. In 1683, it was enclosed, with enough openings made to allow passage for processions and carts. The plaza as a whole is arcaded and enclosed by three-story buildings with wooden balconies, known as "claros." It has been used as a courtyard theatre, for jousting tournaments, religious plays, and bullfights. In 2008, it was declared the 4th Wonder of the Community of Madrid.
The House of the Chain was the lodging of King Philip V during his visit to Chinchón on the night of February 25, 1706. It is a late 17th-century Baroque building with a three-tiered facade and a lintel doorway.

