Things I Love

Moving to Chicago

August 29, 2016
chicago best city ever

I moved to Chicago because it seemed like the most obvious life option. I had moved back to the United States from Rome a few months earlier and was living at my parents’ house in Wisconsin. This was temporary, and becoming more unbearable each day. (I get along with my parents and love them very much, but living at home at 26 after living away for eight years was trying on all of us).

I quit my job in Rome kind of on a whim, with a few freelance clients and a desire to work from anywhere. That anywhere didn’t originally include Chicago. It included Asia, and more of Europe, and lots of Africa, and some South America. Anywhere meant anywhere but the US, especially the Midwest.

When it became clear my freelance clientele wasn’t growing quickly enough to sustain a life of travel, I got a job at a restaurant in Madison. After a few months I had saved enough money to travel or move, and for some reason moving seemed more feasible. I’m still not sure why, as someone who loves travel so much, I made this decision. I think I felt my income was still too unstable to leave for a long period, and that I should focus on getting more local clients and build a reputation in a city. I cancelled a backpacking trip through Asia (that part I still kind of regret) and debated between Chicago and New York City.

chicago flag

I LOVE New York. I always have. It was my dream city. Since high school I planned to move there. But when the time came, I chose Chicago. It seemed easier to break into freelance writing in a smaller, less writer-inundated city, and it’s a lot cheaper. I wasn’t unhappy about the decision, but I wasn’t super excited either.

chicago skyline

I moved into my tiny studio apartment on February 13, 2014. It was one of the coldest days of the year. The apartment looked so much smaller and sadder than it did in photos. The kitchen was practically nonexistent. The bathroom was old and falling apart. The closet smelled like mold. I cried, and didn’t unpack for a few days, running through every alternative option in my head. Was my (bright, spacious) Rome apartment still available? Could I afford a last minute ticket to London? Could I find work in Cambodia if I did go on the trip and run out of money? But I was here, and had spent a lot of money on a security deposit and rent, so I tried to make the apartment as livable as possible.

best coffee chicago

Slowly, the city grew on me. I always liked visiting, but I had never pictured making a life here. I started to work at my neighborhood coffee shop, learned to make the best of a kitchen that doesn’t have a counter, and realized that Chicago is one of the best food cities in the world. (Actually, I think it’s the best, but we can debate).

chicago best restaurants

Once summer came around I was smitten enough with the city that the warm weather, rooftops and patios, and lakefront barely had to show themselves for me to fall in love. Chicago in the summer is absolute perfection. If you live here, the thought of winter and piercing winds never really leaves your mind, so you savor every warm day. Chicagoans don’t take summer for granted, and it’s obvious in the endless events, water sports, neighborhood festivals, and outdoor dining options. These three or four months are so glorious we suffer the rest of the year with resilience and parkas and only a few grumbles.

chicago summer

But winter isn’t so bad either. It really isn’t. We have ice skating and cozy fireplace bars and the lake is beautiful even partially frozen. I’m starting to think we’re actually proud of how cold it gets, warning visitors and talking about the weather more than anyone in any city I’ve ever visited.

Photo Dec 02, 10 03 25 AM

Chicago stole my heart completely, but as you all know, the desire to travel can’t be contained. My freelance work picked up and I’m now able to travel many weeks out of the year. I still visit New York and love it. I still miss Rome sometimes so much I consider moving back for awhile. Last year I spent a few months in London and I’ll undoubtedly spend extended time in other cities as well. I still have a hundred places left on my travel list. But there’s nowhere else I can imagine calling my home base.

lake michigan chicago

That’s why I’m so excited about my latest freelance project! I’m writing the Moon Guide to Chicago, keeping me in town more often for the rest of the year, and enabling me to discover even more about each neighborhood. I am continuously blown away by quality of our local shops and restaurants, by our artists, by our stunning architecture, our beautiful and spacious parks, our fascinating and sometimes dark history, our diversity, and our enthusiasm for this city. I swear you cannot meet someone from Chicago who doesn’t go on and on about it. It’s infectious. I hope I can convey my love for this city and guide readers to the very best we have to offer in every neighborhood. Do you have a local restaurant or business you absolutely love? Please comment or message me. I always tell people Chicago is a big city with a Midwestern feel, and the people are what really make it special. I’d love any help or suggestions you have!

chicago architecture

Thank you Chicagoans for welcoming me these past two years. Expect more Chicago-related posts coming soon! And to all of you readers not from here – I can’t wait for you to visit. 🙂

summertime chi


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  • Reply Sarah G September 6, 2016 at 3:06 pm

    Love this! I agree, Chicago really has a lot of pride and the summers outweigh any sort of bad winter we could have. I have a few fave restaurants and secret spots, but I’ll have to consider sharing them since they won’t be a secret anymore 😉 haha!

    • Reply curiosityandacarryon September 8, 2016 at 8:03 am

      haha completely agree! And I’d love to hear your secret spots! But you’re right, we do need to keep some things from getting too crowded. 🙂

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