A Love Note to Chicago


Wayfaring Rachel: A Chicago-based blog
Exploring Chicago sometimes and the whole world the rest of the time – that’s my current Instagram bio. It pretty much sums up my life, a balance of getting on planes and walking around my city in an effort to know it better.


After over a year in Chicago, there’s still so much to discover. Which museum is the best way to spend a frigid winter day? Which rooftop gives you the best skyline view? And, of course, which coffee shop can I sit in for 6-8 hours and not go crazy?


Getting to know Chicago is a task I’m happily undertaking. In fact, getting on those airplanes has become a little tougher when there’s constantly something amazing happening at home. Travel is part of who I am, but Chicago is the first city the I’ve truly missed while I’m out exploring the world. Coming back here finally feels like coming home.


Here’s a dirty little secret – I didn’t want to move here. I did it for the bigger city, for the opportunities, and yes, for a guy. But I never wanted Chicago, exactly.


Every step of the move was a tug of war between clinging to the people and places I loved before and stepping into the newness. And for someone who is comfortable spending lots of time alone, I was really lonely at first.


Like a lot of relationships, my love affair with Chicago developed from a hundred tiny moments:
    • – The explosion of people onto patios and rooftops on the first nice day of the year. It’s like an unspoken rule that no one goes to work.
    • – Walking through a crowd of tourists and being equal parts annoyed with their sidewalk etiquette and happy I live in a place that people love to visit.
    • – Hearing a cacophony of different languages around you – something I rarely experienced when I lived in other places in the US.
    • – The Chanel-clad woman who slapped away the hand of a pickpocket while he was reaching in my bag on the El.


    • Chicago makes you stronger. There’s a toughness here, paired with that famous Midwestern kindness. I notice the changes in myself the most when I visit other places in the US. I expect more from people now, because Chicago requires you to give more of yourself. It might not be the crushing pace of NYC, but the city is big and cold and not necessarily a place for the naive.


    • Chicago also ruined me. It’s beautiful and full of character, with every convenience you could ever need. I can fully appreciate other kinds of places, and still be really glad to get back to a city with DoorDash and Uber that will pick you up in two minutes or less. Will I one day get tired of cramming into an El car with a hundred drunk Cubs fans headed to Wrigley? Perhaps. And when the city makes me jaded, when I’m more irritated than invigorated by the energy around me, that’s when I’ll leave.


  • Chicago likely won’t be my home forever. If I’ve learned anything in my 26 years, it’s that I’ll always chase the next experience, the next opportunity to grow. But I’m a better person for having been here. When people ask me “Where are you from?” on my travels (and I want to skip the long explanation of my nomadic existence), a simple “Chicago” is my answer. And I’m proud to say it.