Chicago: America’s lakefront metropolis. What makes touring Chicago by boat so excellent? Part of the answer is Lake Michigan, one of the five Great Lakes. Where Lake Michigan and the Chicago River meet became a trading post, then a port, a village, and then finally a city. With so much detail, history, and plenty of shoreline to explore, sightseeing Chicago and its architecture by water on the Aviara AV32 is iconic in its own right.