The architectural boat tour of downtown Chicago is the single best way to see this city in a whole new way. From first-timers to lifers, it doesn't matter how long you've been in town, this perspective is going to be new to all. There are many different tour companies that will take you through the winding waterways of Chicago, you just have to pick the one that is right for you. Tours can range from 30 to 75 minutes, and some boats have no roofs while others have bars where canopies used to be attached. Here are my recommendations for getting the most out of your adventure. First, I'd pick a tour that is at least 60 minutes long, since that will give you all the key sites. Second, if you want to get an unobstructed view (and take the best photos) find a boat with no bars overhead. Third, to get the most educational (and interesting) tour you should use a company that focuses on just that. Chicago is rich in history, and a knowledgeable guide can make all the difference, and I speak from experience on this. The link below is the only boat operator that has a department dedicated solely to education. And fourth, go during good weather and make sure to bundle up if it's cold. This boat tour is always the first thing I recommend to visitors, even before the Willis Tower and all its skyline impressiveness. And while some enjoy looking down on a city, I think that Chicago is one that we can all truly look up to.