It All Began with Chicago: My First Solo Travel Experience


I dreamt of Chicago for years. Mostly in the way we dream of places we’re not so sure we’ll get to go. While working with Air Jamaica (for the uninitiated, that’s the former national airline of Jamaica), Chicago was one of those destinations I always yearned to visit but never made it to, mostly because no one else seemed to want to go and back then I wasn’t one for picking myself up and adventuring solo.

John G. Shedd aquarium - Chicago, Illinois

Photo op in front of the John G. Shedd aquarium

My how things have changed! Fast-forward to 2015 when I decided to shake things up and visit Chicago for my birthday. I was in North Carolina with friends of a friend when I thought, ‘Why the hell not?’ Without overthinking it I went online and bought my ticket on Delta then I proceeded to secure a room at the Chicago Getaway Hostel. Sure hotels were an option, but here’s how I rationalized it. I didn’t know anyone in Chicago so staying in a hotel would mean leaving the same way I came, more or less. And I didn’t want that. I figured a hostel would mean meeting people, and right I was!

Now I wasn’t brave enough to stay in one of those large shared dorms with 10 or 16 beds (yes, my bravery had limits) so I booked a double that I would share with 1 other complete stranger. And that is perhaps one of the greatest examples of serendipity I’ve ever experienced in my life (of course there’ve been others, but this one is worth talking about).

Chicago City Skyline

Posing with Shethal in front of the city skyline

My roommate turned out to be an amazing young woman of Indian descent living in Dubai, and the rest, as they say, is history. She had encountered a Jamaican couple en route to Chicago and we bonded over the tale she told of how exciting it was sharing a flight and a taxi with them (we Jamaicans tend to get that a lot, particularly regarding our personalities. I think there’s something in the water).

Upon learning why I was in Chicago she began planning the weekend’s activities, which started with a sojourn (I call it that because it’s the longest I’ve ever walked in the blistering cold – about 7km). Neither of us was dressed for crazy, schizophrenic Chicago weather, but we didn’t care. It was fun!

We’ve been friends ever since, having visited each other in our respective home countries and we’re currently planning future rendezvous in unfamiliar countries. In addition to that friendship, I celebrated my birthday weekend with random strangers who became friends by the end of the trip. And that, for me, is the greatest pleasure to be found in solo travel – the friendships formed and the thrill of the unknown.

While I have not been back to Chicago since and don’t know when I’ll return (though I seriously need a decent Bean pic – if I don’t have one was I even there?), it will always be the city that nurtured and set fire to my wandering spirit.

Hi, I’m Anna

A girl who traded in her cushy 9 to 5 to pursue a life of travel and passion. Words are my superpower (and also how I pay the bills these days). I love pasta, binge watching Grey’s Anatomy and anything that allows me to flex my creative muscles. I talk travel, dream chasing and living on purpose here on the blog.

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  1. Andrene

    Live in your purpose and enjoy all it has to offer you. Stay strong, and remember you’re not alone, be brave while you fight to live and embrace your truest you.

    • Anna

      Thank you 🙂


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Hi, I’m Anna.

I traded in my cushy 9 to 5 to pursue a life of travel and passion. I talk travel, dream chasing and living on purpose here on the blog. Hope I can inspire you to chase a dream of your own!

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