For a comprehensive overview of Chicago’s skyline, there’s no better vantage point than aboard Chicago's First Lady. You’ll spy more than 50 architecturally significant buildings, from the Wrigley Building to newcomers like the St. Regis. 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. Choose to cruise by day or watch the city light up with an evening option. $52
Even if you're a longtime local, there's something special about taking in the city's architecture on foot or from the water with the help of an expert. From glass and steel castles to ornate Art Deco buildings to street art and cultural landmarks in our neighborhoods, there's a reason these tours are among the best attractions in 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. Here's a few of our favorite tours that are equally engaging for tourists and Chicago lifers.
RECOMMENDED: Check out the full guide to the best Chicago tours