I Fell in Love with Chicago

Have you ever visited a place where you just know that you’re going to fall in love with? Almost like it was just waiting for your arrival like a puppy waits for its human? Yeah. That was me. I fell in love with Chicago from the moment I stepped off of the airplane.

I have wanted to visit Chicago for years and years, and finally the stars aligned.

Well, maybe not the stars.

But the price and weather certainly did. And that was enough for me.

It’s really hard for me to pinpoint the exact moment that I realized that I needed to visit Chicago. Some destinations are easier to recall the spark that ignited the wanderlust – and it usually stems from discovering the location or some other exciting aspect surrounding it.

As an American, I’ve known about Chicago for as long as I can remember. It’s engrained into our brains as naive school children, embedded into our country’s history (both the good and bad), and plays a major role in pop culture.

And maybe that’s where my desire to visit Chicago stemmed…crediting Miss Johnson (my awesome 5th grade teacher), Mrs. Saffle (my unique high school US History teacher), and movies such as The Fugitive and While You Were Sleeping.

I remember studying the city of Chicago while in college, specifically during a post reconstruction-era course (late 1800s). We read the historical non-fiction-turned-novelist-style book, “The Devil in the White City,” which subconsciously rooted a deeper desire to visit Chicago.

Add to that a near-obsession with the board game Ticket to Ride, and you’ve got a recipe that spells: MUST. VISIT. CHICAGO.

the bean - I fell in love with Chicago

For the last few years…well, really ever since I ventured into the world of solo travel…I’ve been dreaming of Chicago. I learned how to search for cheap flights, figured out the secret to navigating new cities for the first time, and taught myself the appropriate amount of research and prep needed to enjoy a new location.

Finally, after years of searching and trying to make schedules work out, I managed to snag a steal of a deal for a weekend solo trip to the windy city.

I was going. I couldn’t believe it.

I was ready to fall in love with Chicago.

fountain - I fell in love with Chicago

Not everyone is ready to fall in love with Chicago the way that I did. And the questions I received about my safety prior to my trip confirmed that thought.

I’ve realized that I am drawn to cities and countries that are a little rougher around the edges. They’re not polished and glamorous in the conventional sense. They’re deeply rooted in their local pride and history. When you visit them, you feel like a true adventurer.

Chicago fit that bill to a T.

It wasn’t even a question. I knew that. I was going to fall in love with Chicago as soon as I deplaned.

And I can’t wait to tell you more about it!


Have you ever been to Chicago? Is there another city that you fell in love with immediately?

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