I rolled into sunny Chicago after a full day of driving. I was exhausted. I’m no fan of driving or parking in that city (trust me, it’s no worth it! You’ll go crazy), so my first challenge was where to drop my car. I’m very fortunate that my friend Erika Napoletano happened to live a neighborhood with an easy parking solution. So I dropped the car and my bike off with her. Then, the task of carrying a carry-on suitcase, backpack and yoga mat through public transportation during rush hour. This may very well have been the hardest part of my journey. I mean, worst than going through city traffic, which affording me the glorious blue water view of Lake Shore Drive.
Two trains and a half mile walk later, I arrived at my friend Megan’s condo in West Loop, where before collapsing on her comfy sofa I demanded with my last breath that everything hence forward be easy.
And it was :). We dined at a delicious mediterranean tapas restaurant right around the corner that had a 7 course tapas special at $33/person. In order to keep our bill at $33/person, we decided not to drink. Then I happily took my sleepy self to bed. My friend’s condo has beautiful natural light, is spacious, and offers great views of the city. With fast wifi, it’s an easy base for work and play.
I had the pleasure of syncing up with another friend and fellow graphic designer, Josh, who relocated from Baltimore to Chicago just a couple months prior. We enjoyed lake side strolls, rooftop views, and connecting with one of my clients at PinStripe Bocce Ball & Bowling Restaurant. The flatbreads here were amazing.
In one of my days of wandering, I had the absolute pleasure of stumbling upon Eataly Chicago, and what a great find. My tastebuds were super happy, and I enjoyed sitting by the bar, watching the chefs prepare pizzas (stretching the dough, sprinkling ingredients) before placing them into the fiery oven. Good times.
My last evening in Chicago included delicious latin fare with my friend Megan at Fiesta Mexicana, followed by seeing Erika Napoletano perform in Washer Dryer at Victory Gardens Theater (go see this, it’s super funny). The following morning I stopped by Erika’s to pick up my car (best believe I took a Lyft!) and then on to my next adventure, a tiny house in Omaha, Nebraska.
Jess Watson is the CEO & Creative Director of Points North Studio. She's the co-organizer of Baltimore Womxn in Tech, a big believer in Baltimore city, and a pioneer of working remotely while traveling the globe.
