Chicago is special. There’s no other way of putting it. A downtown kept beautiful with flowers and green spaces. Fountains. High-end shops filled with actually nice people. But the highlight of any Chicago trip is experiencing the uniqueness of the city’s skyline. Here, buildings are not just square towers, but rather individualized gems. Old buildings and new share the sky, their fascinating features combining to create what might be the world’s most interesting cityscape.

There are two mandatory ways to experience the majesty of the Chicago skyline when you visit: seeing it from above and from below. And while I will try to capture the feelings you can expect to have, it is only via immersing in each of these yourself that you will truly understand why this city is so special.

From Below: An Architecture Boat Cruise

A beautiful day on the Chicago river – a naturally occurring body of water, but one that exists today via man-made measures, as it only connects to Lake Michigan through a lock – is something to cherish. Even with gray skies, the green of the river seems to shine, and Chicagoans all seem to take advantage of livable weather to stroll along the Riverwalk, miles of waterfront boardwalk lined with restaurants and green spaces. Some wave at me aboard Chicago’s Classic Lady as I cruise past. My eyes wander between people watching at river level and gazing up to the sky, squinting to see the tops of some of the country’s tallest buildings. We pass the Wrigley Building and it’s neo-classical dome, turn to view the champagne bottle top of the Carbide and Carbon Building (my personal favorite), sail past the mighty Willis Tower and new St. Regis (now the third tallest building in the city) opening this fall, and countless others. Behind each marvel is another, an endless parade of architectural wonders.

The skyline from the river

There are a lot of companies – and boats – offering this experience, but Chicago’s First Lady cruises partners with the Chicago Architecture Center to create the perfect tour. Each boat comes equipped with outdoor seating and a volunteer from the Center to narrate the entire 90 minute program. We learn about the different architectural styles and how to differentiate them, about the history of many of the buildings, and about some of the fascinating features setting them apart from others. Did you know that the new St. Regis has a completely open floor near the top that allows wind to pass through, leading to greater stability? Did you know that River Point, a LEED Platinum Certified building along the river, uses water from the river as its cooling system and then filters it back? Did you know that the water-level doors of the Tribune plant were never used, as paper was only sent in by train and not boat? With each new view comes a new fascinating factoid.

One of the boats

From my seat in the bow – most passengers are up top, the sun shines off the river and the buildings, and my camera tries to keep up with the steady progress of the tour. Adults and kids alike smile at each new vista, and while not all are as excited about obscure architectural facts as I am, every single person sits in rapt attention, just waiting for our tour guide to tell us all where to look next. We pass kayaking tours, pleasure boats, and water taxis, all enjoying a perfect day on the Chicago River beneath the majesty of the city’s skyline.

A decommissioned bridge for all to see as we sail past

When it is time to end, and we dock back at the corner of Wacker and Michigan Ave., the applause for our now-hoarse guide is thunderous. And rightfully so. I’ve been lucky enough to have had this experience on several occasions now, and it is always – always – both incredible and somehow new. The skyline of Chicago is ever-changing, and this is a truly mandatory way to see it, whether it’s your first time in Chicago or you’re a native. I bid adieu to the vessel, and turn to walk down the Riverwalk with the rest of the city.

The Wrigley Building and its neoclassical decorations

From Above: An Observation Deck

Golden hour, when the sinking sun lights the world in golden hues, is magical in Chicago. As the city moves from day to dusk, lights begin to come on, and the colors of the sunset reflect in the glass facades of Chicago’s buildings. While impressive even from the city streets, it is truly special from up here. I am 94 floors in the air, at the top of the John Hancock Tower at 360 Chicago, my favorite perch in the city. I slowly make my way around the area, experiencing the windows in every direction as the light changes. Navy Pier, River North: these lakefront views to the east and north, respectively, make for remarkable ways to appreciate the coming evening as the lake darkens and the buildings begin to glow. But it is the southern view that captures my heart and soul. Here, Chicago’s three tallest buildings align in front of me, with so many of the other beautiful towers between. I could stay for hours.

The southern view from 360 Chicago. At the far left is the new St. Regis. The far right is the Willis (Sears) Tower, with Trump Tower to its left.

Chicago has two prime observation decks: this one and that of the Willis (formerly Sears) Tower. While the Willis is taller, 110 floors to my 94, it suffers from one major flaw. I can’t see the Willis Tower, the symbol of Chicago’s skyline, from inside the Willis Tower. So for my money, this is the perfect spot to see the city as the birds do.

The Hancock Tower, home of 360 Chicago

Signage directs me to download the Magnicity App, so I do. When in Rome or Chicago… Gazing through the app on my phone screen, I am prompted with information about what I’m seeing. Want to know which building is which? The app, designed for observation decks like this one, and only working here at 360 Chicago, will tell you. Another click shows me where the mighty Chicago fire of 1871 burned. (Hint: most of it.) The app obviates the need for signage that would block the mighty views, for which I am grateful.

As the sun sets, I indulge in a cocktail (my inclusive ticket includes either a beverage or gelato) and watch the lights come on throughout the city. The tops of some buildings glow with color, and looking south I can see the entirety of downtown Chicago spread beneath me. I am king of my domain, standing here atop my throne. The feeling is both powerful and a bit humbling.


360 Chicago has one other feature that is a must-try: Tilt. Guests stand against special windows that then, for only a brief minute, tilt outwards to about a 30 degree angle, allowing me to look directly down at 94 floors of building to the street below before returning my gaze to the city skyline. It seems a bit disorienting, but is completely safe, a one-of-a-kind Chicago experience. Again, my inclusive ticket comes with that feature, the perfect cap to my evening.


Chicago is special, and what makes it so enchanting is the majesty of its skyline. With these two experiences, one from below and one from above, you can truly immerse in the wonder of the architecture and cityscape. For any Chicago visit, these are must-dos.

Thank you to Chicago’s First Lady cruises and to 360 Chicago for hosting my experiences, allowing me to write about two things I absolutely love here in Chicago.

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