Chicago, My First True Love

Twelve years ago this week, cheap I packed up the car with my most valuable possessions – lots and lots of CDs, sales a brand new computer installed with Windows ME and Napster, cheap my best band hoodies and sheltered small-town Midwestern sensibilities – and drove ten hours north. I was headed off to college in the big city. FREEEEDOMMMMM.

I knew that everything was about to change. What I didn’t know at the time was how deeply in love I was about to fall, and that my first true love was going to be a city. I recently headed back to Chicago to begin work with a new client, and I totally had butterflies for two weeks beforehand. I do a lot of business travel, but there’s always something special about going back to Chi-town — the anticipation, flying in over the lake, seeing downtown stretch out. The Hancock tower rising on the north end. The Sears tower on the south. It feels a million miles away from Brooklyn. And it always feels like I’m coming home to welcome arms.

It was one of those perfect weeks. Warm sunshine and golden light during the day, a cool breeze at night. None of the stifling humidity or pavement-melting heat that you grow to expect in the Chicago summertime. The last few times I’ve been back, it’s been perfect. Eighty degrees in October for the marathon, a warm spell in February, and now this. The year I moved there, it snowed the first weekend of October and didn’t stop until March. Chicago, why you tryin’ to woo me back?

This trip, I stayed downtown on State Street and made some time to take photographs and commune with the city a bit — I don’t know if that makes sense, but I don’t know how else to describe it. I do the same thing in New York. Walking around alone in contemplation, observing the ebb and flow of the urban landscape, wandering aimlessly. Watching the way light plays off the buildings, off the sidewalks, catching commuters’ long shadows in the intersections between concrete caverns. There’s something spiritual about the experience, and for me it’s an incredibly important part of being connected to the places you live and love.

I’ve always thought that Chicago is one of the — if not THE — most beautiful city in the US. The compactness of downtown, the consistency of the architecture thanks to the Chicago School, the river that winds slowly through the city and the beautiful industrial bridges that pass over it. Though I’ve never called downtown Chicago my home, in my first year of school I used to stay over a lot with a close friend who lived at the top of the Marina Towers (the corncob buildings above). I spent many hours sitting on his balcony on the 59th floor (or was it the 61st?) just staring out over the city, even in the freezing cold.

Chicago seemed endless. The city stretched out for what seemed like miles, and I could see forever. The sun cast long shadows to the west in the mornings as only the tallest buildings basked in the thin light. At midday you could look straight down and see the precise urban grid bustling with activity. At sunset, the flat western suburban plains turned golden and the colors of the sky melted into Lake Michigan.

And then at night, the lights came on. Oh, who am I kidding. I’m still in love with you, Chicago.

7 thoughts on “Chicago, My First True Love”

  1. I am a big fan of Chicago. I’ve been twice and would still love to go back. It’s the most quintessentially American city I’ve been to in my eyes, more so than New York, San Francisco or Los Angeles of the other big notables.

    1. @Ed — Yes! I do think it’s very ‘American’ in the most traditional sense, and I’ve always thought Chicagoans sort of eschew the super-cosmopolitan trendiness I see in other cities. It’s always awesome to visit the Chi and I love going every time I can! (PS I BET THE YASHICA WOULD LOVE A TRIP.)

  2. Dang, girl, you’re making me cry big missing-Chicago tears. While we get back to visit family every couple years, I haven’t lived there in more than 20 years. My first real jobs, and apartment living were in Chi, post-colelge. Lived in Belmont Harbor and rode the 140 (or was it the 145?) bus down Sheridan Road. Studs Terkel (always wearing red socks) often road the bus. Loved that ride (well, not so much in July and August). Sure felt like I was living the high life. One of the things I loved and still love best about Chicago is the feeling that ‘one side’ is always open due to the lake. Like you said, it’s the light and feeling of always knowing which way is up. What a great place. Of course it’s all super glammed up now, but the old Chicago is still there. Sigh. Smile. Thanks for taking me back:)

    1. Aw, Annie! Chicago is wonderful, I agree. That’s hilarious about Studs Terkel. And it’s kind of funny — when I got to NYC I always tried to go out of the way to take the bus when I could because it was so familiar to me from my Chicago days. I don’t do that so much anymore, but the slower pace and the people-watching are second to none.

      Yeah, Chi is more glam now and it’s a little confusing. One night while I was there, friends took me to some artsy restaurant that served white balsamic vinegar ICE CREAM with a caprese salad — whut?! It was strange and unexpected — not the food, but the fact I was in CHICAGO!

      Anyway, hope you get a chance to go back some! xoxo

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