While in the Windy City aka: Chicago do as the locals do. Stay near the Magnificent Mile, go take pictures next to the jersey clad Harry Caray statue at Wrigley Field, and hit up all the attractions with my iPhone camera on and ready to capture every millisecond. Ha. I kid. I have no idea what the locals actually do here in Chi-town so I'll stick to blindly thinking it's the tourist stuff.

Chicago, like most great American cities, commercialize nearly everything: sports, art, architecture, food, and of course, shopping. Fun fashion fact: there was time when Chicago was the epicentre of mail order catalogue retail fashion. Biggest in the world I just found out via my river tour guide. Oh catalogues. 

Some of my earliest - and fondest - holiday memories are compliments of the Wishbook edition of the Sears catalogue. There was something so special to me about flipping through its pages as many times as I wanted - pestering siblings aside - and fantasizing about what items may be under the holiday tree in a few months. (Yes I've always been nutty about shopping and gifts).

See, in rural Saskatchewan there was no Sears store in my town. There was no online shopping yet. I was one of thousands (millions maybe) little kids dutifully marking off the pages of her potential wish list marvelling at the options all in one thick catalogue. With the Wishbook I was granted the opportunity to dream a bit. I could pretend that I could be as metropolitan as the fancy models seemed to be. 

As a young child I knew that Sears - and my beloved Oprah - came from the same city: Chicago. Fast forward a couple decades later and I'm finally here. Oh and Obama. One of the most exciting things about coming to a new city - besides the shopping I always seem to find time for - is getting a sense of the vibe. I try to soak up and process what the feeling on the streets are. I get onto public transit and see where people are going and doing with their day. I keep in mind that the cushy tourist downtown spots I stay in are not a typical slice of the city pie but that's all I really get the taste for. Anywho, Chicago - to me - is a less frantic NYC. There's a pulse but it isn't as agitated as the big apple nor is it as sleepy as San Francisco. Lucky for me there's lots to do (besides shopping). 

The Art Institute? Why, yes. Thanks for the the absolute delight going through a totally immersive and might I say absolutely huge collection that spans the lifetime of humans and their experiences. 

How about taking in the architectural phenomenons packed along the rivers edge? You bet. Happy to report I learned a lot not only about the different styles and periods of the key players' work, I brushed up on history too. Fire here. Leak there. River and lake locks a plenty. Simply put Chicago river tours are bursting with anecdotes and facts from the trading and mercantile days. 

Want to go way way up the Willis (formerly Sears) Tower? You bet. All 103 floors. At the top you are treated to spectacular 360 degree views of 4 different states, all the high rises, and one hell of a sunset if you time it just so. As I walked around the top I thought about the business that used to be conducted below in that very skyscraper. I thought to myself, "What if one of those Sears orders placed all those Christmases ago made it to a floor in this buildings?" What a trip. 

I'm both sad for the former glory of the Sears company and touched that I, like many kids all over the world, maybe too thought about the big Windy City as the place responsible for all the goodies received over the years. My eight-year-old self thanks you.