The earliest information about the Danubian port urban formation Kilia-Licostomo exists in the documents drawn up in the 14th century by the Genoese. Later, the overall image of medieval Kilia is shaped by different categories of sources. The first iconographic representation of New Kilia was made in the 16th century by the illustrious of the Ottoman miniaturist and calligrapher Nasuh Matrakçi. The settlement is described by the Turkish traveler Evliya Çelebi, the Austrian merchant Nicolaus Ernst Kleemann and others. The planimetric situation of medieval Kilia is fixed in several graphic documents made by the Russian or Ottoman military engineers at the end of the 18th century. Taking as a basis, the topographic plans of Kilia from the years 1770, 1790, 1794 and 1815, as well as the prospectus-perspective of the fortress from 1770, we made an attempt to reconstruct the urban dimensions of the city. The urbanism of the medieval settlement follows the trajectory of urbanism evolved over time, with the non-geometric street network, crossed by streets parallel to the river line and those converging towards the fortress. The general plan of Chilia from 1815 proposes the first solution to systematize the city according to the “Hippodamic” principles.