Chicago is one of my favourite cities. It is vibrant, clean, friendly, and approachable. I’ve been there twice, spending a week in 1999 and stopping over on my Great Lakes adventure in 2005 to return to Navy Pier. I also went through O’Hare on my way to Colorado in 1996, but I’m not sure that counts. 🙂

Until I visited Chicago in 1999 I considered myself to be a country gal with little use for cities, finding them to be ugly. Vacations were meant to be spent in aesthetically pleasing places; I had only come to Chicago to visit a friend, otherwise I would have spent my travel dollars on a great camping excursion instead.

My week in Chicago changed my opinion of cities in general and Americans specifically. Until Chicago, I thought all American cities were like filthy New York City and all Americans like its rude residents. I still had a lot to learn about not making sweeping generalizations about places and people.

One of my last stops during that 1999 trip was Navy Pier, a tourist trap jutting out into Lake Michigan that is filled with souvenir shops and over priced food. It’s one of my favourite places in the United States. 🙂

I walked down one side of the Pier that day and up the other, stopping in my tracks as I did so to take in the sight of Chicago. It awed me. Glimmering obsidian sky scrapers shimmered against a perfect blue sky, their reflections bouncing off the turquoise waters of Lake Michigan. I was looking at a downtown traffic snarl at the same time as I watched volleyballers frolic on a sandy beach. Cities can be beautiful, I thought with awe.

(I went through a long spell of traveling without a camera)

Six years later, I decided to return to that spot on the Pier and it was as though time had stood still. Chicago was exactly as I remembered her to be and while a stay over wasn’t on the plate for this trip, I was reassured that my memories hadn’t been romanticized over the passage of time.

Chicago taught me that cities can be beautiful, a lesson that I clung to as I so desperately worked to fall in love with Vancouver.