Where did Miss O’Leary’s cow supposedly start the Chicago fire? Learn all that and so much more on Shoreline Sightseeing Cruises, which run about 45 minutes as you travel down the Chicago River. While the architectural and skyline boat tours are a big attraction for tourists, locals can get something out of this too. Enjoy a $5 beer while being regaled with historical tales of the Windy City, all the while relaxing on the boat deck. This isn’t a boring high school history lesson. The entertaining tour guide combines stories about well-known buildings with little-known facts. Architecture still not your cup of tea? Shoreline also organizes and hosts Fireworks cruises during the Summer months. Tickets typically start around $24, depending on what kind of cruise you choose.