Still tired after yesterday’s exhausting flight we ventured to do some sightseeing in Chicago. First stop was in Chicago was Jay Pritzker Pavillion.
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Chicago Bean Sculpture
Second thing to see on our list was Chicago Bean sculpture in the Millennium park.
This silver sculpture affectionately known as “The Bean“, but officially named “Cloud Gate“. Designed by Indian-born British sculptor scultpor Anish Kapoor, construction on the sculpture began in 2004, and it was officially unveiled in 2006. Its seamless surface reflects the city skyline, the sky, and the people around it like a funhouse mirror, inviting interaction and playful photos. Because of its unique shape and the way it captures the surrounding environment, it’s incredibly popular, drawing crowds who love to walk around it, touch its smooth surface, and capture their own distorted reflections within its curves.
Crown Fountain in Chicago
After we took a stroll along Millennium Park we stumbled into the Crown Fountain, where random faces were spitting out the stream of water from their mouth. It did look impressive.
This interactive public art piece was designed by Spanish artist Jaume Plensa and opened to the public in 2004. It consists of two fifty-foot glass block towers that display changing video images, primarily close-ups of Chicago residents’ faces. Periodically, water spouts from the mouths of these projected faces, creating a playful and often crowded splash pool at the base, especially popular during warmer months.
Route 66 Road Start Sign
Then we visited Route 66 road start sign, which is not impressive anymore as some vandals put a lot if stickers on it.
Of course, no trip starting in Chicago with Route 66 in mind is complete without finding the official “Begin Route 66” sign. It’s not a giant monument, mind you, just a standard street sign, but finding it marks the symbolic starting point of the legendary Mother Road. Due to its iconic status and the sheer number of travellers eager to mark their journey, you’ll often find it covered in a colourful collage of stickers left by previous adventurers. While this adds to its character, it also means the sign sometimes shows signs of wear and tear or even minor vandalism – a small price, perhaps, for being the starting point of such a legendary road trip.
While strolling along the street we found another Route 66 sign. This one was cleaner, no stickers on it. The tourists must be not aware of this one yet!
Wills Tower
Speaking of iconic Chicago sights, one structure that absolutely dominates the skyline is the Willis Tower, formerly and still often called the Sears Tower. This towering skyscraper was once the tallest building in the world and remains a truly impressive sight. Visiting its Skydeck on a clear day offers breathtaking panoramic views of the city and even across Lake Michigan, making you feel like you’re on top of the world!
Stepping out onto the Skydeck’s glass floor was, shall we say, an exhilarating experience – gazing straight down hundreds of feet felt more than a little scary. I could have sworn I heard the glass creaking underfoot, adding a delightful layer of suspense! Thankfully, we decided to go quite early in the day, so we managed to get into the building without another epic queue, though we still enjoyed a brief 30-minute wait inside. Anyhow, it was absolutely worth it; the view of Chicago from up there is simply amazing, sprawling out like a miniature city below. It actually reminded me a bit of the view of Manhattan from Rockefeller building, but with the added bonus that the entrance fee ($23) was much cheaper than the Rockefeller tour (~$40) – a small victory after our travel woes!
After soaking in those incredible views from the Skydeck, we decided to take a stroll along the Chicago River. It’s a fantastic way to see the city’s famous architecture up close. Walking along the riverwalk, you get to admire all sorts of buildings, from historic structures to modern skyscrapers, each telling a part of Chicago’s story. It was truly beautiful to see the city from this perspective, a perfect way to wind down after our busy day.
Return Visit Statue
As we geared up to officially start our Route 66 journey, we made sure to visit a classic roadside icon, although not a traditional Muffler Man this time: the “Return Visit” statue. Created by Seward Johnson in 2014, this striking 31-foot, 19-ton painted bronze sculpture depicts Abraham Lincoln in a modern setting, standing alongside a “common man” who holds the text of the Gettysburg Address. Patterned after a life-sized version first shown in Gettysburg, this larger-than-life piece has traveled to various locations, including being displayed right here in Chicago in front of the Tribune Tower. Its powerful intent is to highlight the continuing relevance of Lincoln’s historic address in today’s world, offering a thought-provoking start to our journey down the Mother Road.
When we got exhausted we went and sat down in the beer garden.
The newspapers already mentioning the big event – Solar Eclipse.
After our refreshing break (you know, the one involving beer), we decided the best way to soak in more of Chicago was on two wheels. Renting bikes (only $10 each) felt like a stroke of genius, and honestly, cruising along the lakefront bike path was the absolute highlight of the day! It was incredibly relaxing, a welcome change from airport queues and towering buildings. The path itself is amazing, smooth and wide, and that light breeze coming off Lake Michigan? Pure perfection, offering a much-needed cool-down while we enjoyed the stunning panorama of the Chicago skyline stretching out before us. It’s a whole different perspective from being hundreds of feet up! Plus, the whole scene felt so relaxed, with people jogging, cycling, and simply enjoying the beautiful day – a stark contrast to the earlier urban hustle.
Our ride took us down towards the Adler Planetarium. While we didn’t venture inside this time, the location itself offers another fantastic vantage point. From the area around the planetarium, you get a truly spectacular view back towards downtown Chicago, seeing the familiar skyscrapers from a new angle. It’s a great spot to just pause, take it all in, and appreciate the city’s impressive layout against the backdrop of the vast lake.
Since we only had our bikes for an hour (renting them cost a certain amount per hour), we needed to make sure we returned them on time. Therefore, we took a lovely route back through Grant Park, which is a beautiful green space right in the heart of the city. Along the way, we made a quick stop to admire the famous Buckingham Fountain, a truly grand and impressive landmark. We also zipped quickly past The Field Museum, another massive and interesting building, getting just a glimpse of it as we peddled by. Also passed by John G. Shedd Aquarium.
Buckingham Fountain is one of Chicago’s most famous landmarks and a truly impressive sight. It’s a large, ornate fountain that serves as the centrepiece of Grant Park. Dedicated in 1927, it was designed to represent Lake Michigan, with four sets of sea horses symbolising the four states that border the lake. The fountain is known for its elaborate water displays, especially the impressive centre jet that shoots water high into the air, and it also features a light and music show in the evenings during the warmer months.
Being thoroughly (and perhaps a little delightfully) tired from our cycling excursion, we made a dash back to another bike rental point near Millennium Park to return our steeds within the hour limit. Since, cycling on the sidewalk is apparently illegal business, I was a bit stressed out riding them. With sidewalks so wide they feel like dedicated bike highways, it seemed everyone was doing it! It was quite the experience, and we even managed to pass by some police officers who didn’t bat an eye when we asked for directions – perhaps they appreciate the efficiency of the sidewalk cyclist.
The streets were so wide, that even crossing one seemed like walking a marathon.
Once we successfully dropped off the bikes, we decided to stroll down the magnificent mile towards the John Hancock Tower (875 North Michigan Avenue), aiming for a cocktail bar with a view. I was fully prepared for us to be turned away, given our travel-worn shorts and decidedly awful trainers, but apparently, they don’t care about dress codes when there’s a tourist with cash involved We only had to queue for about 10 minutes or so, and then we were whisked up to the 96th floor, free of charge for the entry itself. The cocktail prices were quite steep, but honestly, they tasted great, and the view from up there, especially at night, was easily worth twice as much. It was a perfect way to cap off a day of unexpected adventures and iconic Chicago sights.
The final accent of the day was taking metro. It normally used by poor people and tourists. We tried to book 5 tickets and machine told me it was . I have inserted 20. Then it notified that we have inserted more than we need, we pressed continue. Guess what? It kept all change! No change given as it was written on top of the machine. The weirdest thing was that receipt came out for only! So 5 is not taxed and doesn’t exist, basically given tax free to somebody.
As we were finally leaving the heights of 875 North Michigan Avenue, we made a stop in the lobby. And there, we encountered the truly amazing sculpture “Lucent” by Wolfgang Buttress. Honestly, after a day of travel woes, immigration marathons, and slightly terrifying glass floors, this sculpture was probably the best thing I’d seen all day. It’s one of those pieces that just draws you in, a beautiful and unexpected find right there in the building’s entrance.
The final “exciting” accent of the day was our decision to take the metro – a mode of transport apparently favoured by those seeking an authentic local experience (or perhaps just trying to save a few bucks). We attempted to book five tickets, and the machine informed us the total was $11.25. Feeling confident, I inserted a twenty-dollar bill. The machine then politely notified us that we had inserted more than needed, and we just pressed ‘continue’, fully expecting our change. Guess what? It swallowed the entire twenty! Absolutely no change was given, despite a little sign somewhere on the machine that probably mentioned this in fine print. The weirdest part? The receipt that popped out was only for a fraction of the amount we paid! So, it seems that the difference is neither taxed nor officially accounted for – essentially a tax-free donation to… well, who knows? A truly memorable introduction to Chicago’s public transit system!
Tomorrow finally we were hitting the road Route 66!