A Tale of Three Cities: Choosing Between Portland, Chicago, and Columbus

Photo credit: John Mueller, CC BY 2.0.

Last July, I packed up my stuff in my Cavalier in Chicago and headed out west for Portland. In the months before I left, I carefully planned my move and made arrangements to keep my day job from afar. I even documented my last 100 days of living in Chicago in immortal, indie movie montage form.

Today, I’m planning the logistics of going back to the Midwest. The week before Halloween, I’ll be driving my car and my stuff to Columbus, Ohio, the city I left for Chicago six years ago. This move wasn’t planned the way the one that brought me out here was, but life doesn’t always go the way you expect, right?

I’ve written before about my complicated feelings about my move to Portland. (TL;DR? Rain! For many months! Seasonal Affective Disorder, nooo. I know, I’m a jerk to act shocked about dismal weather in the Pacific Northwest, but here we are.) I didn’t expect to feel this way a year later, but as it stands now, while I had a good year of living on the West Coast and met a ton of awesome friends, I miss my family. The distance between us has been more felt than I anticipated.

What I Wanted From My Move to Portland and What I Got

I’ve dreaded telling Portland friends about my move, but it’s even harder to explain when I talk to my friends in Chicago. If I’m going to leave Portland, why wouldn’t I just go back to the Windy City? I worry that my choice makes it look like I’m passing judgement on Columbus as a better city, but it’s a lot more complicated than that.

Chicago, Portland, and Columbus are three very different cities, with different things to offer. But I am here to compare some of the many attributes I’ve considered as I’ve contemplated my future. With that in mind, a tale of three cities, and what each brings to the table.


Writer Dana Norris recently wrote a piece comparing Chicago and her new home, Cleveland. One of those factors, she wrote, was what people say back to you when you tell them where you live. Cleveland gets an unfair rap in that regard. But Chicago has the name recognition, for sure. Unlike Columbus or Portland, you’re not going to confuse anyone with the nonexistent Chicago, Georgia or Chicago, Maine. Illinois all the way, son — the one, the only. Whether I want to admit or not, there’s an appeal to that.

Cleveland vs. Chicago, a Scientific Breakdown

Cost of living

According to CNN Money’s cost of living calculator, having a $50,000 salary (the default search setting) will get you less in Portland than either Chicago or Columbus. $50K in Portland is the equivalent of $45,249 in Chicago and $35,280 in Columbus.

Since I am keeping my remote marketing gig, my current Portland salary will carry me farther in Columbus than it would in my other options. Groceries go for 17 percent less there than in Chicago, comparable to 19 percent less than in Portland. Oddly, utilities in Columbus cost 16 percent more than in Portland (but still 6 percent less than in Chicago). Why are utilities in Portland so cheap?


I’m about to get priced out of Portland, and man, I just got here. I can’t afford a house here or in my old Chicago neighborhood, but swinging a mortgage in Central Ohio could be doable. Maybe. I’m not sure, I’ve never bought a house before and have no idea what the first step is. But according to that CNN calculator, the cost of housing in Columbus is an astounding 53 percent less than Portland, and 43 percent less than Chicago.


I didn’t realize how spoiled I’d been by the Chicago Transit Authority until I got to Portland. Portland is hugely progressive in terms of biking and pedestrians! And they’ve got lots of transit options. They just don’t necessarily run as frequently as Chicago’s busses and trains do. Columbus has a bus system, but it’s still a city in which I would feel like I’d need to own a car. I’ll be keeping my Cavalier and running it into the ground, but also continuing to pay $70/month in car insurance. Once I hit town I’ll start spending a lot more in gas since I’ll be using my car more. I know once I get back to Columbus I’ll miss Portland’s streetcar, not to mention its frequent bike-friendly events.


Midwest winters are not for the faint of heart. The winter before I moved to Portland, I would constantly check the weather app on my phone, furiously comparing the temperatures between Chicago and Portland. It would be in the low 40s in the Pacific Northwest and, like, negative five outside my Chicago ‘burbs office.

The thing is, even though it rarely dips below freezing in Portland, you still don’t want to be outside. It’s raining. It’s been raining since November, and will continue to do so until May or later. Even as I write this, the first day of summer has passed and it’s been raining all day. It snowed once here this past winter, and the city shut down in a panic. I was surprised by the joy I felt at the sight of it. I took my Texas-raised friend out in it and delighted in her amazement. Still, because the temperatures didn’t dip, my skin was flawless all winter and I don’t think I used lotion twice. Major summer weather bonus: Portland lacks the humidity from which the Midwest suffers.

Desirability in terms of things I, a 30-year-old woman, enjoy

A testament to all three cities I’ve lived in — they all have amazing beer and artisans. A guy I once dated tried to insist that Ohio had more state pride than any other state when it came to crafts handmade in its image. However, having lived in Illinois and Oregon, I feel like maybe that dude just didn’t see the same state pride fervor having grown up in Arizona. Hey-oh!

Anyway. All three cities and states are filled to the brim with awesome artists, and with great breweries. Chicago’s Ravenswood and Lincoln Square neighborhoods have seen a beer renaissance in recent years, and Portland is, well, Portland. That said, Columbus is holding its own. Take a look at this National Geographic article from June that mentions a slew of microbreweries that have cropped up in Central Ohio recently.

Why All the Cool Kids Love Columbus, Ohio

I find myself looking into local roller derby rec leagues and coworking spaces in Columbus — the exact same things I was doing just a year ago, in preparation for getting to Portland. I just made a Twitter list of Columbus writers and creatives I want to meet up and work with. I can’t believe how excited I am to go back to a city I left six years ago. I don’t know how long I’ll stay there, but I know I need to be there for now.

Meanwhile, I’ve got about 100 days left of living in Portland, and I’m going to make them count. And yes, there will be a video.

Meryl Williams is a Portland writer who is chronicling her life as a roller derby girl via her awesome TinyLetter. She loves Rilo Kiley and most cheeses.

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