The windy city is mighty pretty!

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The windy city is mighty pretty!
Chicago, IL

Chicago, IL


This is my first time in Chicago (with the exception of an overnight stay after a missed connection between Vancouver and New York over a decade ago in the dead of an extreme winters night). My reason for coming here was simple – I had to come via here to get to Vancouver so I might as well spend a few days and see what’s here.

Once I started looking into Chicago as a destination though, I couldn’t believe that we hadn’t been here before! For anyone with even a vague interest in architecture, skycrapers especially, this place is a veritable playground! Despite yesterdays slow start out of the gates, today I was filled with an urgency to get out there and see and experience as much as I could in my limited time.

I made a bee line to the structure I most wanted to see, more of a sculpture really – The Cloud Gate by Anish Kapoor, more affectionately known as ‘The Bean’. Instantly recognisable from its various appearances on the big and small screen, it is basically a giant silver reflective bean that invites people to walk around and under it, interact with it and see themselves reflected in its surface with the inimitable Chicago skyline and surrounding Millenium Park. Unfortunately, the rest of the park was off limits today for the swearing in of the new mayor.

Already, I was surrounded on all sides by countless significant buildings that I stood no chance of interpreting on my own so I headed to the Chicago Architectural Foundation to see what could be arranged in terms of a tour. According to my watch it was just after midday yet the gentleman at the counter seemed to think I could still make the midday boat tour which started a 15 minute walk away. It was at this point I realised I hadn’t adjusted my watch and that my early night last night was even more pathetic. None the less, I was excited to have a precious hour back.

The boat tour obviously went along the river system which afforded a perfect view of some of the most significant buildings. There is no way I can begin to recount them but each seemed to lay claim to being the tallest, the biggest, the widest, the most steel, the curviest, the brightest and so on. Luckily it was a perfectly sunny day and all these superlative structures just glistened in the sunlight.

Back on shore, it was an opportunity to get a close up at some of the finer details of certain buildings but also get in amongst it and see some of the landmarks not visible from the river. I’d read that one of the best views to be had was from the El Train – an elevated train track the runs in a loop around the city. With my three day pass in hand, I went to see if it was true – it was. I did a loop in each direction before heading up the ‘Magnificent Mile’, named presumably for the high end boutiques that line it.

At the top of the Magnificent Mile stands the very brooding and imposing Hancock Tower, once the tallest structure in Chicago, now coming in at a mere number 3. Very impressive none the less with a viewing tower up the top which claimed to have the best views in the city. I contemplated going up and was struck by the comparison with the competing New York tower experiences – The Empire State Building vs Rockerfeller Centre – on the one hand, the Rockefeller Centre’s view includes the Empire State and offers a more modern and comfortable experience but on the other hand, The Empire State is The Empire State – it’s just got to be done. With that in mind, I bid farewell to the Hancock Tower and made my way to the tallest building in America – The Sears Tower.

There was still plenty of light in the day but it was late enough that I could time my visit for day and night views. With that in mind, I explored some more juggling a heavily marked up map, a local guidebook and my Wallpaper Chicago guide for all your hipster but not very practical needs – such was my desperation not to miss a thing.

Just before twilight I headed up The Sears Tower (officially now The Willis Tower but no one acknowledges it, like Centrepoint in Sydney). The labyrinth to the lift made the CN tower look like a hop, skip and jump – it was so convoluted that I was starting to worry it would already by dark by the time I got to the top. Luckily it wasn’t thanks to the long spring days. I was even able to write out a few postcards while I waited for the sun to set.

When it finally did, it was spectacular! Happy people everywhere taking each others photos, a guy up one end proposing in one of the glass floored cubes to the cheers of the crowd, just so romantic… why do I like these towers? There’s not even anywhere for you to jump off it in times of desperate need! Hmph!

Back on the street it was already quite late, too late I decided to start another adventure out to Wrigleyville in search of The Chicago Diner so I headed back to Wicker Park to check out a pub I’d read about called The Map Room, apparently lined with maps and globes and cosy little nooks, it sounded like my kind of place. It wasn’t. There was a chipped painting of a map on a wall with the wrong kind of paint, one globe and all the nooks were occupied by happy couples who seemed to have somehow beaten me there from Sear Tower. I stayed for one, head in a book and left.

Despite a few bum notes at the end there, it was an extraordinary day into which I couldn’t have fit another thing and I’ve only just scratched the surface!


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