1. Chicago Architecture Foundation River Cruise
This Chicago architecture tour is a must for entertaining family and friends from out of town or just orienting yourself to the city’s many architectural wonders. With a knowledgeable docent in tow, you'll cruise along the Chicago River from River City north to Goose Island, taking in stunning, unimpeded views of some of the city's most famous skyscrapers along the way. On the river, you'll take in over 40 landmark buildings, including towers from the Tribune to the Trump. There's a bar too, just in case. Reservations are strongly recommended.