Chicago Trolley Company offers guided tours on a fleet of rubber-wheeled “San Francisco–style” trolleys that stop at a number of popular spots around the city, including Navy Pier, the Grant Park museums, the historic Water Tower, and the Willis Tower. You can stay on for the full 2-hour ride or get on and off at each stop. During the summer, the trolleys also offer trips to residential neighborhoods, and I highly recommend the West Neighborhood Tour. The witty guide sums up the history of Chicago, points out iconic buildings, and fills you in on the diverse neighborhoods, while also driving through Chinatown, Pilsen, and Little Italy; you can hop off for dim sum and then hop on the next trolley and continue on to tacos followed by pasta, and you never have to worry about navigating public transportation or search for parking. The trolleys operate year-round and are enclosed and heated during the chilliest months. The same company also operates the Chicago Double Decker Company, which has a fleet of London-style red buses. The two-level buses follow the same route as the trolleys; if you buy an all-day pass, you can hop from bus to trolley at any point.