Chicago Blew Me Away…

While I have previously spent time discussing sports and my strange appreciation for “big data” and sales, another one of my true passions is travel.

That said, I thought I would pepper in trip debriefs every now and again. This is the first installment.


Shortly after graduating college in early 2015 and beginning a career in software sales, I was confronted with the first of many new opportunities. Time and money.

In all the years up to this point, I had never really been offered the free time to journey off and explore new places. Whether it was baseball tournaments, long nights studying, or weekend-consuming jobs to pay for college, travel was never an option. Besides, what college kid has enough money to spend on anything other than books these days anyways?

That said, with my newly found “big-boy” salary and liberal vacation policies at my disposal, travel would soon become my new obsession.

First stop, Chicago.

Leading up to my trip out, I was truthfully nervous about the journey. Not having been to an airport in almost 10 years, I had a strange sense that things were going to be much more complicated and confusing than what I remembered. They weren’t. I made it to my gate with an hour to spare…Ironically, as I look back now, I’m convinced I was more worried about navigating through the airport than actually getting on the plane.

Nevertheless, I had succeeded in step one — and as I sat in my seat, looking down onto the foreign city below, soon to be home for a week, I couldn’t help but anticipate the adventures ahead.

Exiting O’Hare (a little intimidating for a first time traveller), I was quickly greeted by my old friend Chris, who had graciously offered for me to sleep at his place for the week. We hit the ground running, immediately.


Quick pause for a soapbox.

Many people have asked me over the past year about what goes into my travel “plans.” More specifically, what plans do I make before heading off? Conveniently, the answer has relatively stayed the same, “Nothing.” Aside from the necessary sleeping arrangements and transportation components, I tend to leave my days open to chance.

While people travel for all sorts of reasons, including business, a break from reality, running from something at home, looking for a fresh start, experiencing new cultures/environments, or simply wanting to check things off the old bucket list, I tend to travel for something a little different. Direction. Every time I travel, and choose to “fly by the seat of my pants,” it never fails that I learn something new about myself. Whether it be a new passion, a new perspective, a new skill, or simply something I should never do again, I tend to walk away with a sense of accomplishment. For this, the urge to travel never really subsides.

Off soapbox.


After spending the first night in Chicago bar hopping a few of the local spots with my host and his friends (which I always recommend doing), I ventured out on my own for the next three.

Carrying nothing but a laptop and camera on my back, I hopped on the public transportation system (CTA), and started hitting the “must-sees” — googling all along the way. During those three days, as typically true for most of my travels, I stuck to a steady dose of yelp’d coffee shops and Thrillist restaurant suggestions. I can’t say for certain which shops or restaurants I liked the most, but I can say with full certainty that each one had its own Chicago flare — robust flavors, eclectic sports memorabilia, and a touch of class (except for the hole-in-the-wall pizza joint of course; it was strictly sports memorabilia). I sprinkled in a few obligatory sightseeing excursions as well.

Day four and five were mostly spent with Chris. He had taken both days off and wanted to show me “his side” of city. Apparently him and his girlfriend love shopping, eating, and dancing, because between the two days, we went to three separate shopping centers, bought more clothes than my trip home allowed, ate enough food to feed an army, and danced at multiple local hot-spots each night. Looking back, some of the most memorable moments were made during those two days. Not only did we explore different districts and local dive-bars that I would have otherwise never experienced, but I also felt like I got a sense real for the people of Chicago.

Surrounded by “Southern Culture” my entire life, I had little experience for something different. What I found in Chicago was just that, different. And I liked it. Chicago was fast and the people were even faster. While I do appreciate the occasional small talk here in the South, I found the contrasting efficiency in speech and action rather appealing. Unfortunately, I think this business-like behavior often gets misunderstood by people on the outside looking in, as rude or arrogant. Although I think some of this may be true, the core motivation seems far-less vain than perceived. Regardless, I throughly enjoyed my time spent connecting with the locals.

With only one day left, I had one thing on my mind; Wrigley.

For a former player like myself, Wrigley has become somewhat of a baseball mecca — especially in the age where new stadiums are the norm. That said, the Cubs happened to be in town for the week and on my last full day, they had a double header. I had to go.

I was able to pick up a ticket for a seat behind home plate for game one and set aside time to bar hop Wrigleyville for game two. Now there was only one thing left to do beforehand…

On my way up on the red line train, I googled the best place to grab a “Chicago-style” dog and quickly found myself at a trailer-like structure just blocks from the stadium — eating an authentic Chicago dog just minutes before the first pitch at a Cubs’ game. If bucket lists were something I kept, go ahead and check that off.

After finishing, quite possibly the best hot dog of my life, I headed for the stadium entrance. Accompanied by a sea of blue and red, I walked under the famous Wrigley sign and through the gates. As I journeyed up the stairs, past the rows of people, and to my seat, I was immediately met with chills (weird, I know). For a brief moment, I had stepped back in time and couldn’t help but picture the legends who had once played on the field below. Surreal.

Poetically enough, it was a great game, with the Cubs winning on an 8th inning rally and an Aroldis Chapman 103 MPH fastball to seal the deal. (They would eventually go on to to win the World Series later that season; their first one since 1908.)

The following morning, I hopped on the CTA train one last time and headed for O’Hare —luggage in hand. Exhausted and drained, I boarded my flight. I was headed home and my first solo travel journey was in the books.


It has been almost a year to date since I made that trip to Chicago and yet I still think about it pretty regularly. I’m not sure if it was the initiation to travel or the personal journey I was on that made it so memorable, but something was unique about that trip. When I look back, I see it as somewhat of a starting point. A starting point for a new journey; a journey of exploring the new.

Chicago is a special place to me for that reason and I can thankfully say I have made it back twice since…