Before the arrival of the European explorers and fur traders, the area around Winnipeg was shared between the Assiniboine and Cree First Nations. Winnipeg, named after the Cree word for "muddy waters" became the center of commercial fur trade rivalry between the North West Company and the Hudson Bay Company during the early 19th century.

Lord Selkirk of Scotland led Scottish and Irish immigrants to the area where Fort Garry was built; the first permanent settlement by the Europeans was formed in early 1812. Winnipeg was connected to the rest of Canada by railway in 1881, which resulted in the rapid growth of the town, creating a 30-year period of growth and prosperity unequalled in Canadian urban development.

A flood of immigrants, high wheat prices, plentiful capital and improved farming techniques contributed to making Winnipeg the wholesale, administrative, and financial centre of western Canada. Following World War I, economic stagnation due to low wheat prices and the Depression lasted well into the 1940s. Since 1945, Winnipeg has grown steadily, based on its position as a major grain, financial, manufacturing, and transportation centre.

During the 1970s and 1980s, Winnipeg underwent considerable redevelopment and improvements. 1997 is a year marked in the minds of Winnipeg residents forever; as they fought the Flood of the Century for a 2 1/2 week period starting April 21st. Approximately 8.1 million sandbags were filled and delivered in the city, in order to protect property and homes from rising flood waters.

The sandbag diking effort required over 200,000 volunteer days, where one day is equal to an eight-hour shift. In addition, earth dikes were built around the city for fortification. During this time over 9,000 city residents representing 3,000 homes had to be evacuated.

The total estimated flood costs in the City were $51 million. Today this provincial capital is now known for its classic mid-western style of architecture, which can be found surrounded by old and modern buildings giving it a reputation for the “Chicago of Canada.”