
Think of a skyscraping skyline and you may not immediately think of Chicago. Located on Lake Michigan, the famously dubbed Windy City is, in fact, the birthplace of the skyscraper – and today its skyline is believed to be among the world’s tallest and densest.
It all started with the Great Chicago. It levelled the Windy City leaving only a few buildings such as the Chicago Water Tower on Michigan Avenue still standing. It became a symbol for a city determined to rebuild something innovative.
This created an opportunity for architects to try new and innovative ideas to rebuild the city. “The Chicago School” was a group of architects who enthusiastically promoted load bearing masonry and steel frame construction for the new buildings and some of these are truly incredible pieces of architecture.
This is a whirlwind tour an amazing collection of buildings that form a concrete and steel canyon within just four square miles.

Chicago Riverwalk
Walk along Riverwalk for a mile and a quarter by the blue-green waters of the Chicago River from Lakeshore Drive and Lake Street not forgetting to look up even though you may find yourself straining your neck to look upwards.
You’ll see the Trump Tower tower over the Wrigley Building on Michigan Avenue. There’s also Art Deco, Modern, International, Beaux-Arts, and even Spanish Colonial Revival style buildings.
Even the bridges across the river are stylish and made of riveted steel painted a dull red some with stone bridge towers.
The Milestone Mile (and shopping at Michigan Avenue)
A building boom started with the revolutionary, double-decked steel DuSable Bridge over the river at Michigan Avenue. It has huge bridge towers of Bedford stone that are carved with scenes. The bridge serves as a Beaux-Arts style gateway to The Magnificent Mile of stores along Michigan Avenue.
Rising high is The Wrigley Building (Spanish Colonial Revival), the London Guarantee & Building (Beaux-Arts), the Chicago Tribune Tower (Gothic Revival) and the Art Deco structures of the Carbide and Carbon building with its gold leaf adornments and the skyscraper at 333 N. Michigan.
Michigan Avenue runs North from the bridge and allows you to shop some of the famous stores along the first “Magnificent” mile where you can shop at Bloomingdales, Marshalls, Neiman Marcus, Tiffany’s, Disney, Nike, are just a few.

The view at John Hancock Center
The crenellated Water Tower sits across the avenue from the dark exterior of the huge John Hancock Center with its 360 Chicago observation deck a thousand feet above the street.
Next door is a multi-story mall called Water Tower Place that has a Macy’s and a very cool Lego store that has a display of the Chicago skyline created out of Legos in its front window.
TIP: There’s a Harry Caray on the seventh floor though the original Harry Carays on Kinzie Street with its white-jacketed waiters, memorabilia, and Frank Nitti cellar is a more genuine Chicago experience.
The Chicago River Architectural Tour
The Chicago River Architectural boat tour cruises past the Merchandise Mart which was the largest building in the world when it was built. Its four million square feet along the river covers more than two city blocks within its Art Deco walls.
A more modern “Chicago School” of architects built the first steel and glass towers along Lake Shore drive. I saw examples of this new Mid-Century Modern style with buildings like the twin circular towers of Marina City. It was built and in addition to residential space, it included an office building, a theatre, gym, swimming pool, ice rink, bowling alley, as well covered a marina for your boat.
The river changes from green to brown as the tour boat turns into the south branch of the river due to Lake Michigan which flows into the Chicago River carrying its green algae along with it.
Chicago rerouted the waters of the Chicago River to create this reverse flow of water to help clean its polluted waterway and the water of Lake Michigan. The river is now a source of pride and beauty.