(Surprisingly) Blown away by the Windy City

As a travel addict based in Toronto, I am permanently planning escapes to countries that offer wildly different landscape, tantalizing cuisine, a foreign language and exotic culture.  Admittedly, I never thought I could find all of that and more during a weekend getaway to Chicago; as it turns out, I was wrong.

Known as the Windy City, or the Second City, having been rebuilt following a fire that brought the city to the ground in 1871, Chicago proved the perfect place to unwind for a weekend of relaxation coupled with a little bit of discovery. My husband and I landed on Friday night and checked into the Swissôtel downtown. We had flown with Porter airlines from Toronto and had enjoyed a glass or two of wine to kick start the weekend (coupled with an incredible view of the Toronto skyline) into the just the right gear.

After dropping off our bags, we headed over to Millennium Park where we spent a solid fifteen minutes distorting ourselves in “the Bean”, formally known as Cloud Gate. By then, hunger had kicked in and we decided to take a stroll up Michigan Avenue, veering left towards a restaurant called Dos Diablos. Shamefully, I had no idea that over 40% of the foreign born population in Chicago is Mexican. As I chewed my way through a delicious empanada, I realized that less than three hours into our trip, I had stumbled upon foreign cuisine and a culture different from my own; who knew?

Still in search of eye catching landscapes, we woke up on Saturday and left for Old Town, purchasing our day pass for the overhead train that runs in and around the downtown loop. The train tracks were built using steel, as is everything in Chicago, and run straight through the city centre, a testament to the role of the steel industry until its collapse in the U.S late in the twentieth century. Truth be told, I’ve never been overly impressed with the appearance of steel (or any metal really – I’m more of an ancient tone type of girl), but the way Chicago continues to celebrate their history by incorporating steel design into city planning is pretty impressive, even to a steel skeptic like myself.

We jumped off the train near Armitage in the northern end of the loop and stepped into a quiet residential area that was transformed by green lush as far as the eye could see. My husband proposed at once that we both start looking for jobs in the city; I wasn’t fully convinced. As we walked toward Lincoln Park however, even I started wondering what it would be like to live in a place that so successfully combined small town charm with big city feel. Suddenly, we emerged out of the residential area and wandered straight into the Lincoln Park Zoo. I was pleasantly surprised to learn that admission was free and that, despite my hesitations about entering into a run-down complex with rotting gates and tired animals, most of the pens were well maintained. I was also surprised to see that, despite free admission, the zoo housed some really big animals like polar bears, tigers, cheetahs, rhinoceroses, and, my personal favourite, the giraffe.

After mingling with the primates, the reptiles and some really big cats, we strolled through the remainder of Lincoln Park, cutting into the Old Town triangle just north of the city. Old Town proved a great place to grab a bite (and a drink) and gives off a really funky vibe that nearly mimics the trendier parts of downtown Toronto. I can see why people refer to Chicago as the city that Toronto wants to be in a few years time; cleaner, greener and committed to providing free attractions aimed at increasing community engagement.

With feet that were tiring quickly, we decided to make use of our day pass by hopping on a bus that brought us to Navy Pier. Navy Pier is a long pier extended outwards into Lake Michigan, and owes its name to the number of regiments stationed along the pier during WW1 as well as the pilots and troops who were trained on-site for the navy during WWII. The pier, whose entertainment roots date back to when it hosted the World Fair in 1893, remains home to a number of restaurants, theatres and entertainment venues, attracting upwards of 8 million visitors each year.

While the pier is a nice place to stroll, it does fill up rather quickly on sunny Saturday afternoons, so we decided to boot it back to the hotel, slip into some more comfortable attire and head to Millennium Park. There we found ourselves, bottle of wine in hand, lying on a blank “borrowed” from the hotel, listening to a free performance of An American in Paris, being performed by a visiting orchestra on tour; perfection.

If I was still unconvinced of Chicago’s landscape, Sunday quickly affirmed that I had jumped to conclusions far too soon. Before leaving Toronto, we’d been told that we simply had to take an architectural cruise up the river and since I’m not going to argue with throngs of people telling me the same thing, first thing Sunday morning, we boarded a boat that completely changed the way I looked at the Chicago skyline.  As we toured up and down the Chicago River, which is more a circuit of rivers and canals than one steady body of water, I finally understood the luster of visiting a city of skyscrapers.

Walking among the buildings, and without the historical context to back things up, it’s hard to understand the fascination with Chicagoan architecture. Once however, you see the variety of approaches and styles merged together in a panorama of steel, concrete and window panes, it’s like looking at a painting whose objects make little sense unless strung together in a series of interlocking patterns and designs. The most memorable buildings along the tour were definitely: Boeing HQ, a large chunk of which is supported by a lever at the top and pillars below designed to ease the concerns of citizens passing by; the Merchandise Mart, which, built in 1931, was the world’s largest building until the construction of the Pentagon in 1941; Aqua, a building designed in a nautical theme with balconies that allow neighbours on each level to interact and is the largest project ever awarded to an American firm headed by a woman; and Marina City, two cylindrical towers designed by Bertrand Goldberg in an effort to move away from the typical prairie style architecture used frequently throughout Chicago.

Following our cruise down the river, we decided to take one last jaunt through Millennium Park by day only to discover Buckingham Fountain and a welcome (shady) escape from the blistering heat.

Following our day-time excursion, I came to the realization that I had grossly underestimated the value of discovering cities that, for whatever reason, didn’t make my top ten or twenty… or simply didn’t make the list at all. Too much international travel had turned me into a travel snob! So, in an effort to ground myself, I whisked my husband off to Giordano’s for a big slice of deep dish pizza, a local speciality and sinfully delicious.

I willingly succumbed to my love for Chicago and thanked my husband for forcing the visit. Watching England lose that day to Italy in the Euro Cup quarter finals, I found myself humbled on multiple fronts.  Never again will I forego the opportunity to explore places that seem too familiar; I’m slowly learning just how very different they can be.

6 thoughts on “(Surprisingly) Blown away by the Windy City

  1. I’ve been reading and seeing a lot of praise about Chicago lately, and this is only making me regret that I can’t go there on my US trip next year even more! Although I shall be in Toronto next June with no plans after that, so maybe a quick trip down to Chicago is in order? Hmm…

    Actually scratch the, “hmm” and replace it with “if at all possible” – I just looked at that photo of the deep-dish pizza again. Droooooool.

    1. Hi there! A trip to Chicago is definitely worth the visit – if only for the deep dish pizza (granted, the architecture is also, pretty amazing)! From Toronto, you can definitely make the trip to Chicago (just over two hours) – keep an eye on Porter airlines and their special fares (sign up for newsletters and great deals via alerts). Have a great trip!

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