Chicago, USA: Part I – A Whirlwind Time in the Windy City

Another eventful trip – albeit without any actual jet-setting – was a family trip to Chicago in 2006 to witness my uncle become the International President for the Loyal Order of Moose, a nonprofit organization with aims to unite and support communities. While the main focus of the trip revolved around celebrating with and seeing the official start to my uncle’s one year term, we were there for several days and had the chance to see quite a few sites.

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As with many road trips, getting there is half the fun! Family members were driving or flying from several Canadian locations, but – as seems to be the case for my family – we all had a great story to tack onto our travel. For instance, another of my uncles who was flying in had a very turbulence-heavy flight followed by a nerve-wracking landing. In his words, “we were flying so low I could see what this one guy was barbecuing!” Upon arrival, it was to discover that his luggage had been misplaced. For our vehicle, five of us were crammed into a car with no A/C. While that wouldn’t be the worst thing in the world, we were stuck for over an hour in bumper-to-bumper, non-moving traffic with no wind as relief from the heat. Worst of all, my cousin Michael’s window wouldn’t roll down, so he was stuck with the hot sun beating down on him. It was only after we arrived that he discovered the manual child lock switch, found in the side of the door, had been activated. Even though we were the first to approach Chicago, another van-full of family members reached the city before we did. Hilariously enough, we still beat them to the hotel, thanks to the confusing roadways known as Upper Wacker Drive and Lower Wacker Drive. We were staying at the Hyatt Regency Chicago, which is found on East Upper Wacker Drive. My relatives were lost on Lower Wacker Drive, and drove around for ages before they found their way out. Word of caution if you’re driving in Chicago – that area can be tricky.

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My cousin Leah – who has always been more like an older sister – and I were thrilled to have a hotel room to ourselves. From there we discovered our true mission for the duration of our Chicago trip – find the pool on top of a nearby roof.


As it turned out, the pool was part of a gym complex. The man behind the front counter gave us each a mug with little Chicago-related souvenirs after we admitted to trying to track it down for several days. As far as I know, I still have the mug somewhere.

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The first night was a family-oriented catch up night, but the next day was beautiful, sunny, and the perfect type of weather for a little exploring.

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Chicago is actually a fairly cool city, particularly when it comes to the architecture. It has a very memorable skyline, and the Chicago River running alongside our hotel made for a picturesque nature break among all the man-made structures.

This will probably sound ridiculous, but one of stops that day was one at one of my favorite stores. Since we don’t have too many of them in Canada, it was a treat to go there.

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Yup, the Disney store. I feel absolutely no shame in admitting that I love animated movies, and Disney just happens to have some pretty darn good ones.

After the Disney store, we did our best to track down a Target, which ended up being harder than it seemed. We were walking everywhere, and kept trying to ask locals for directions. After over 45 minutes of walking around and looking, Stephen called out, “I feel like we’re on The Amazing Race!”. It was pretty accurate, since none of us had our phones with us – no thanks, roaming charges – and we weren’t carrying a map. Super prepared. Eventually we found it, and it came with a surprise – escalators for your cart.

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Maybe I was just getting dehydrated and delirious from all the craziness of trying to find a Target by foot, but I was delighted by this.

During our time in Chicago, we took both the subway and the “L”. The L is elevated over the Chicago roadways, spanning over the downtown and creating a whole new vantage point from which to observe.


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Of course, there was still plenty to see by foot as well, and sometimes even too much. With one section we passed, I have now seen more leather chaps and pants with the asses cut out than any one person needs to see in a lifetime. Even better, my younger sister Jen – only 8 at the time – was there to see it all, too.

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One of our days was spent on the water, admiring the Chicago River and skyline from boat. I have to say it was pretty impressive.

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Stay tuned for another Chicago post including my favorite memory of the trip, and the best thing – in my opinion – to come from the Moose.

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