For a comprehensive overview of Chicago’s skyline, there’s no better vantage point than the water. You’ll spy more than 40 architecturally significant buildings, including the John Hancock Center, the Wrigley Building, the Aon Center and Willis Tower, as you drift along the Chicago River. An expert guide will give you the lowdown on Chicago’s rise from the Great Fire of 1871, the advent of balloon-frame construction and other crucial moments in the city’s history. $43.68
If flying buttresses, Tiffany mosaics and Gothic columns get you all hot and bothered, you’ll love these fascinating architecture tours of Chicago. Nerd out over the design, engineering and construction behind the most beautiful buildings in Chicago on guided walks, bus rides and boat tours. First-time visitors will be happy to know that these architecture tours double as sightseeing walks of the best Chicago attractions—you might even be able to snap a few Instagrams along the way. Even if you don’t have a clue who Frank Lloyd Wright was, the best architecture tours of Chicago are almost guaranteed to leave you inspired.
RECOMMENDED: Check out the full guide to the best Chicago tours