Chicago Architecture Foundation River Cruise

As a major metropolis, Chicago hands-down has better architecture than New York. There are some really striking buildings (from the predictably ostentatious Trump building being built right now to long-standing art deco buildings) and the water-ways running through Chicago provide the perfect vantage point to take them all in.

According to our hotel concierge, the Chicago Architecture Foundation Cruise is the best to go on since they have some of the most knowledgeable guides. Ours certainly was. She rattled off facts and dates and architecture styles for close to two ours throughout the duration of our cruise. Very impressive.

Note: even in July in the middle of the day it can be a bit brisk on the boat in the shade - or at least it was during our trip. If you're just precisely comfortable standing stock still in the sun when you're there, best to bring a sweatshirt or something on the boat with you, just in case.