Chicago is one of those cities that feels larger than life the moment you arrive. I had planned to have a good view from my window seat on Lufthansa. Unfortunately, due to a strike I was stuck in the middle of the United plane instead. Fortunately, I arrived four hours earlier than the original plan. That gave me the opportunity to drive into Chicago at daylight and enjoy some blues at night.
Chicago & Lake Michigan from John Hancock Center
Although many might say, the skyline rises out of Lake Michigan, for me it rose above the highway as I drove through a building on ground level and it rose many stories from there. The city is like a monument to ambition, and every block seems to tell a story about reinvention. It is impossible to understand Chicago without understanding the Great Fire of 1871. The flames destroyed most of downtown and out of that devastation came one of the most remarkable rebuilding projects in American history. Architects and engineers suddenly had a blank canvas, and Chicago became the birthplace of the modern skyscraper.
Rookery, 1888, 55 m
The best way to appreciate that history is to begin with an architectural walking tour through downtown. I used an especially memorable option which is the Secret Interiors Architecture Tour through the Loop. Instead of focusing only on the outside of the buildings, my guide Talia took me during this two-hour walk inside some of Chicago’s architectural treasures.
Union Station, 1925
As I was the only one, I got a private public tour starting at Union Station, the route passed through South LaSalle Street and visited interiors such as the Rookery Building, the Marquette Building, the Field Building and the old Board of Trade district before ending near the Marshall Field building (we also went in). Along the way we saw soaring domes, glittering mosaics, marble staircases and intricate craftsmanship that most visitors never discover. The tour also explains how Chicago architects solved challenges of light and structure, and how the city’s buildings shaped architectural trends around the world.
Lobby of the Rookery, designed by Frank Lloyd Wright, 1905
Elevator panel in the Field Building representing the building, 1934, 163 m
Mosaic in the Marquette Building, 1895, 62.5 m
The Palmer House Hotel, 1870/ 1925
I paired the walking tour with a river cruise for the full experience. From the water, the city opens up completely. Looking up from the Chicago River, you can appreciate the skyline as a whole and understand why Chicago became the birthplace of the skyscraper. The contrast between historic masonry towers and gleaming glass high-rises is especially dramatic from the river, turning the city into an outdoor museum of architecture.
St. Regis, 2020, 363 m
tallest building designed by a women (Jeanne Gang)
Reid Murdoch Building, 1914
One building always dominates the conversation and the skyline: the Sears Tower, now officially known as Willis Tower (but nobody calls it that way). For decades it was the tallest building in the world, and even today it still feels impossibly tall. The highlight is stepping out onto The Ledge, a glass balcony that projects from the side of the building more than 1,300 feet/ 396 meters above the street. Looking straight down between your feet is both terrifying and exhilarating, especially if the day is clear enough to see far across Illinois and into neighboring states. At first I had planned to visit for sunset on Saturday but rain, clouds and fog blurred the view as I could see on the webcam, so I rebooked my visit for Sunday morning.
On the ledge - glass and a lot of air between me and the street
Sears Tower, 1974, 527 m (incl. antennas)
Not far away stands another Chicago icon, the John Hancock Center, now often simply called 875 North Michigan Avenue. Its 360 Chicago Observatory offers a different perspective from Sears Tower. Instead of looking down into the dense center of downtown, you get a sweeping view over Lake Michigan and north along the shoreline. Sunset is the perfect time to visit, when the city begins to glow and the lake turns deep blue. And that's more or less the time I chose - nearly the last thing I did before returning to the airport. There is a parking garage for a high fee - I paid 41$ for just over an hour.
John Hancock Center/ 875 North Michigan Avenue, 1969, 457 m
Chicago - an hour before sunset
Chicago is at its most festive in March. Every year for St. Patrick’s Day, the city dyes the Chicago River an astonishing shade of bright green. It is one of those traditions that sounds impossible until you see it for yourself. Crowds line the bridges and riverwalk to watch the water transform, and suddenly the whole city seems to join the celebration. The company I used for the river cruise also let's the plumbers use their boats for dying the river.
Green River at 150 North Riverside
Explanation on the architecture
From Sears Tower
Friday evening is the perfect time to experience Chicago’s music scene at Buddy Guy’s Legends. The legendary blues club has hosted some of the greatest names in music, and there is no better way to spend a Friday night than listening to live blues in a city that helped shape the genre. As I arrived earlier in town, I went there for dinner and by that secured my seat for the performance of opener Matt and headliner Santini.
Santini
Art Institute of Chicago
Chicago is also rich in culture beyond its skyline. The Art Institute of Chicago is one of the great museums of the world, with masterpieces ranging from Impressionist paintings to American icons. You can spend hours wandering through the galleries and still leave wanting more. I came there to see some famous paintings by American artists and was captivated by "Paradise Lost" by Raqib Shaw. I could only capture many individual sections of this 100 foot masterpiece - for a full view go here.
A short distance away but not good connected with public transport, the Shedd Aquarium offers a completely different experience, with beluga whales, sharks, penguins and colorful tropical fish set against the backdrop of Lake Michigan.
For a more urban side of the city, spend time along the Magnificent Mile. This stretch of Michigan Avenue is famous for shopping, grand hotels, and historic buildings. Even if you are not interested in shopping, it is worth walking the avenue simply to absorb the atmosphere and admire the architecture.
Magnificient Mile
I used Chicago City Pass (paid 120€) to access most of the sights, save money and skip the line. The pass included one-time admission to Shedd Aquarium (40-52$ - dynamic pricing) and Skydeck Chicago (32-55$), plus a choice of 3 of the following attractions: Shoreline Sightseeing Architecture River Tour (46-52$), Field Museum (30$), 360 CHICAGO Observation Deck (29-38$), Griffin Museum of Science and Industry (26$), Art Institute of Chicago (14-34$), and Adler Planetarium (40$).
If you have time to leave downtown, make the short trip west to Oak Park. This quiet suburb is closely associated with Frank Lloyd Wright, one of America’s greatest architects. Oak Park contains the largest collection of Wright-designed homes anywhere in the world. His Home and Studio is the obvious starting point, giving a fascinating glimpse into the place where many of his early ideas were developed. Nearby stands Unity Temple, one of Wright’s architectural masterpieces and one of the most important modern buildings in America. The best way to explore Oak Park is on foot. A walking tour with audio guide through the neighborhood reveals house after house designed by Wright, each one different and inventive.
Chicago is a city that rewards curiosity. It is a place where history, architecture, music, food, and art all come together. The skyline may be the first thing you notice, but it is the stories behind the buildings, the blues drifting out of a club on a Friday night, the green river in March, and the quiet streets of Oak Park that make Chicago unforgettable.
The alleys between buildings with fire escape stairs like in the movies
No trip to Chicago is complete without trying something uniquely local, and one of the city’s great roadside institutions is Superdawg. With its retro drive-in atmosphere, neon sign, and famous hot dogs topped in classic Chicago style, it feels like stepping back into another era. So this was my last stop before driving off into the sunset and to the airport for my flight home.
My Superdawg
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