When the Christmas carol "saw three ships come sailing in" they could have been singing about Chicago in 1831. While shipping was about to explode on the Great Lakes, in 1831 ships were still a rarity.
Chicago wasn't actually a city yet but a small village of log houses and wigwams squatting around Fort Dearborn. The fort, built originally in 1808, was burned to the ground during the War of 1812 by the native people in an attack known as the Fort Dearborn Massacre.
The fort was rebuilt in 1816 and used again by the military, but in the spring of 1831, the Napoleon arrived to remove the last of the troops. That was the first ship. In July, Joseph and John Naper's Telegraph brought settlers and supplies to the Chicago community. In November, Captain Stuart anchored the Marengo off shore in Lake Michigan for the last contact until winter was over.
The sailing season was ruled by ice on the Great Lakes, sometimes not breaking up until May. Captain Stuart was probably racing to get back to Detroit before the lakes froze. Meanwhile, Chicago started building their lighthouse again to be ready for spring's first schooner.