30 Days of Indie Travel Project: City

The prompt for Day 15 (the halfway point!) of the 30 Days of Indie Travel Project* is City.

What is your favorite (or least favorite) city and what do you love (or hate) about it?


Sweet home Chicago.

Oh, what a love-hate relationship we have.

Shortly before I left Chicago in August to start my current year of traveling, I wrote a sort of “Dear John” letter to the city, bidding it adieu. I never got around to posting it then, but given today’s prompt, I thought I’d share it now:

Dear Chicago,

It’s not you, it’s me.  Really. I mean it.

It was love at first sight when I first met you back in 2000, a 3-month summer fling that left me wanting more.  So I made the commitment and moved here the next year, fresh out of law school, completely enamored with all you had to offer.

I was 25, a young attorney at a large law firm and you had everything I thought I wanted.  I had my high rise apartment with a view of Lake Michigan. VIP access to the hottest clubs. A nice paycheck that let me spend my weekends strolling down the Magnificent Mile doing more than just window shopping.  A never-ending list of new restaurants to explore. Sandy beaches to cure my volleyball craving in the summer.  A great circle of friends (mostly lawyers) to share it all with.  Life was good.

But gradually things changed.  You didn’t change, Chicago, I did. 

After a while the club scene got old and I grew tired of wasting my Saturdays hung over from the previous night. And after a while the lawyer thing got old as I didn’t appreciate eating half my meals at the office and my dates didn’t appreciate me being tethered to my Blackberry. I moved further north, away from the tourists downtown and the fresh-out-of-college 22 year olds in Lincoln Park. Friends started marrying and I saw less and less of those who meant the most to me, while surrounding myself with an increasing number of bar friends in an attempt to keep my social life going.

I left the large firm for a smaller law firm and then got out of the law altogether.  I took tennis lessons and volunteered.  I started running.  I signed up for an improv class. But something was still missing. The spark just wasn’t there anymore.

Don’t get me wrong, we had some great times.

Boat cruises on Lake Michigan.

The magic and misery of the 2003 Cubs.

Jimmy Buffett at Wrigley Field.

Old St. Pat’s World’s Largest Block Party.

Prince at the United Center.

Early morning runs along the lakefront.

Election Night 2008 in Grant Park.

Late nights at Carol’s Pub.


The Twelve Bars of Xmas bar crawl.

Snowmageddon 2011.

Fear Experiment at the Park West.

But, as with any relationship that has run its course, I feel like lately I have really just been going through the motions.  Once I had the epiphany that I wanted out, Chicago, part of me mentally and emotionally checked out as well.

I even tried to resurrect the love this summer, creating my Ultimate To-Do List for Summer in Chicago.  But in the end, it was too late.  I was too busy, too focused on my next steps, to make it through even half of the list.

So goodbye Chicago.  It’s been a good 10 years and I’ll miss you.

And who knows?  Maybe I’ll be back eventually, begging and pleading for you to take me back.



*Throughout the month of November, BootsnAll is inviting bloggers from around the world to join them in a daily blogging effort – the 30 Days of Indie Travel Project –  designed to reflect on how our travel experiences over the last year – or whenever – have shaped us and our view of the world. Bloggers can follow the prompts as strictly or loosely as they like, interpreting them in various ways and responding via text, photos or video posted on their own blogs.

Missed a day? Check out my previous posts for the 30 Days of Indie Travel Project. You can also read posts from other bloggers participating in the project by following the #indie30 hashtag on Twitter or visiting the BootsnAll page on Facebook.

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