Malcom began aquiring property in what is today downtown Chicago about 1842.
We cannot know a complete story of his ventures there because the records were lost in the Great Chicago Fire of 1871. The icons on the map below show the properties he owned at his death, which he distributed to his grandchildren in his will.
His will described some of the lots as having "houses" on them. The houses on others had burned in the Great Fire of 1871, which he directed his executors to re-build. These "houses" were typically three to five story apartment buildings with stores on the ground level.
His will also mentioned that he had previously given "certain lot and houses" in Chicago to the children of his daughter Martha, but no details of those properties have been found.
Drag the yellow figure to the icons to see what is on the property today.
It may help to zoom in first.