Architecture Tours in Chicago

There are few better ways to get a broad overview of Chicago’s architectural significance than on a cruise of the shoreline. This sightseeing boat ride covers three branches of the Chicago River, taking in skyline icons like the Willis Tower, Jeanne Gang’s shimmering Aqua skyscraper, and the distinctive Spanish Colonial Revival Style of 1920s stalwart the Wrigley Building. Along the way, you’ll learn how Chicago rebuilt after the Great Fire of 1871, see how its architecture has evolved over the years, and hear about the city’s pioneering approach to skyscraper construction in the late 19th and early 20th centuries. There will also be a photo opportunity or six at historic Wolf Point.

Top tip #1: If you’re in the market for something a bit more in-depth, the Chicago Architecture Foundation cruise is a good bet. This one’s led by bona fide architecture experts who should be able to answer all your most pressing questions about the city’s prevailing styles, as well as ticking off the feats of engineering innovation that led to Chicago having more movable bridges than any other city on the planet.

Top tip #2: the standard shoreline architectural sightseeing cruise is included with a pass from Go City, which can save you up to 50% on entry fees when sightseeing in Chicago and also includes access to several Frank Lloyd Wright attractions, plus the Field Museum, Shedd Aquarium and more. It also includes a guided tour of Chicago’s Riverwalk, which gets you even closer to downtown titans including the Tribune Tower and Jewelers Building, once the tallest building outside of NYC.

Book a guided tour or go it alone on a self-guided walk of the Chicago Loop in the heart of downtown. Here’s where to get up close to some of the city’s best-loved architectural masterpieces. We’re talking the likes of the Willis Tower with its space-age modular design, which held the record of world’s tallest building for nearly a quarter-century before Malaysia’s Petronas Towers took the title in 1996. Then there’s the Chicago Cultural Center with its distinctive Tiffany glass dome, the Rookery with its Frank Lloyd Wright-designed atrium, and the Monadnock Building, a monolithic early skyscraper, built way back in the 1890s. At 215 feet, the Monadnock remains the tallest load-bearing brick building ever constructed. They don’t make 'em like they used to.

Chicago led the world in skyscraper construction, with its first (indeed the world’s first) high-rise going up in 1885. Run by the Chicago Architecture Center, this tour of the Windy City’s most iconic tall buildings calls at the site of the aforementioned Home Insurance Building (sadly no longer with us), plus the opulent Art Deco grandeur of the Carbide and Carbon Building (pictured), and the Reliance Building, one of the world’s first fully glazed high-rise buildings. Expect fascinating insights into Chicago’s early urban development, plus photo opps at some of the oldest steel-framed buildings on the planet.

No visit to Chicago would be complete without nabbing a selfie or six in front of (and underneath) Anish Kapoor’s extraordinary Cloud Gate sculpture, better known as ‘The Bean’. This huge gleaming icon creates twisted, ever-morphing reflections of the surrounding cityscape and its inhabitants. You’ll find it in Millennium Park, where Frank Gehry’s astonishing Jay Pritzker Pavilion is a futuristic vision in stainless steel and makes for a memorable venue for open-air concerts. Also in the Millennium Park neighborhood, Renzo Piano’s design for the Art Institute of Chicago’s Modern Wing is another fine example of modern architecture. And the collection within – Matisse, Picasso, Kandinsky, Dalí, Miró and more – is no less spectacular.

If your appetite has been whetted by our round-up of top architectural tours in Chicago, you’ll be pleased to know that many of the tours mentioned above are included with a pass from Go City. The pass can save you up to 50% and includes entry to Frank Lloyd Wright attractions, plus a movie locations tour, the Skydeck Chicago observation platform at the Willis Tower, the Griffin Museum of Science and Industry, and more. Click the buttons below to find out more and choose your pass!