Back in the 19th century, the concept of a Chinese Town was first conceived by Sir Stamford Raffles. Dissatisfied with the haphazard way the settlement around Singapore River and Boat Quay had developed with the sudden influx of immigrants mainly from China, Stamford Raffles issued a plan proposing a Chinese Kampong to the Town Planning Committee in 1822.

When Raffles drew up the area plan for Chinatown, his blueprint was developed from years of first-hand experience in Penang, that those native buildings unprotected from intense heat of the sun and monsoon rain were impractical. His instructions to the Singapore Town Planning Committee in 1822 thus stated that houses should have a uniform type of front each having a verandah of a certain depth, open to all sides as a continuous and open passage on each side of the street. This probably led to the "five-foot way" that the shophouses in Chinatown are famous for. Some researchers have speculated that the shophouse was a fusion of the narrow-fronted houses that are a familiar sight in Amsterdam with the ones of Southern China, especially in Guangzhou and Fujian.

Many buildings in Chinatown were destroyed during the Japanese occupation of Singapore in the Second World War. In recent years, through the government's conservation efforts, many of these buildings have been restored to their former charms, thus offering a unique window to the past, a glimpse at how the early Chinese settlers lived and toiled.