Watch the weather Paul
I grew up on the lakefront and sailed out of Belmont Harbor racing a Rhodes 19 as a kid. Lake Michigan can be very treacherous in the spring and summer months as storms move through (west to east). Waves are never uniform and choppy and the whole Lake Michigan "bowl affect" can be hellish when the weather gets bad. With that, catch the weather forecasts and if you do venture out make sure your weather co-operates.The skyline of Chicago is incredible from the water! If its your first time, the best boat tours where you can get a great view of the city is out of the Shedd Aquarium. Its been years for me, so I hope they are still in business, but the tour boat is in fairly large open (double deckers), and its a blast! Take a drive along Lake Shore Drive and try to head north up Sheridan Road (runs along the lake into Evanston (Northwestern University), and the northern suburbs. Its a beautiful time of year up there and a very scenic drive. Keep the museums in mind (Natural History, Science and Industry, Shedd Aquarium, Adler Planitarium, etc.). They are some of the best in the world. Have a great time.By the way are you docked at Sunrise? Hunter?Bob