Requesting your thoughts that may help me decide between moving to Chicago or Portland (Oregon)?

rip_rike
2026-03-28T23:35:39Z

hey there tildes. i’m moving out of texas in august no matter what and am trying to decide between chicago and portland. i was wondering if anyone here has lived in either (or both) locations and could help me decide by sharing their experiences.

i’m currently in texas and by the time i move, i will have only been here 1 year but this was always supposed to be a temporary stop for a job (that is very much not working out due to the owner of the company — i’ve posted about it a few months ago and struggle with it in my mind to this day).

i’ve moved around a bit, both in the same cities and across several states, over the past 5 years. im tired of moving and starting over, so im really going to focus on making the next place work for at least 5 years. the world is too chaotic for me to pretend to see farther out than that.

i had been reading and watching a lot of videos about chicago over the past month or two and now wondering if i should give it a try? i just assumed i would move back to portland by default because i liked it well enough and now im not sure if i should fall back to something familiar or try again somewhere else.

just want to say that i know moving wont magically make my life great and i know i will have to put in a lot of work to make everything work regardless. greener grass and all that.

portland

i’ve lived in portland before (2 years) and visited many, many times in the 7 years before moving there. i liked it for the most part.

things i didn’t like (mostly my opinion/experience)

PNW gray, dreary weather for many months. im prone to bouts of severe depression and it’s a lot of work to keep healthy during the dark months. was in for seattle for 7 years prior to living in portland so i was maxed out with the gray perhaps.

cost of living is kind of high for the size of city and offerings

it’s a very slow, sleepy city that feels more like a very big town than a small city. sometimes i liked this about the city (less traffic, crowds) and sometimes i didnt (less “things going on”, especially later at night)

the sheer amount of unsheltered people and seemingly no solution or even progress. when i lived there, it was really, really bad (2021-2023) and i’ve read that it’s actually gotten worse since ive left. it’s heartbreaking.

things i did like

green year round, even if it’s gray and winter. beautiful outdoors/hiking, swimming in the river

proximity to seattle (i have friends there)

much more agreeable politics for me (Leftists everywhere)

great food options, fun bars, interesting shops

very bike friendly (newly into biking, was not when i lived there)

decent public transit

relatively friendly people though i did struggle with making deeper connections

very positive towards folks who are queer or generally nontraditional. that’s important to me

seems like a lot of creative folk live here

why i moved away from portland originally

i moved away because i was deeply unhappy with my work life (had two awful jobs in a row because my freelancing work (audio/video editing) dried up completely), had to get a roommate for the first time in like 10 years because of pay decreasing with new jobs, and tried to change up my medication for depression (for reasons i can no longer recall) that backfired and i fell into a massive bout of depression.

i backed away from all of my friendships and spent all of my time dreaming about greener grass. instead of focusing on getting a better job and fixing my medication, i chose the “easy” route of moving away again and starting over.

i went to denver chasing better weather and had two new clients lined up but two months after moving, they stopped paying me. had to take one to court and everything. only other job i could find was awful with a really toxic manager and a huge pay cut (again) but had no other job options. i did fix my meds and other lifestyle changes so all was not completely lost.

the owner of the company i was working for (and before i knew what kind of person he was) offered me a new job in texas so i jumped on it. my family was there so figured it’d be nice to be nearby for a year or two. unsurprisingly, san antonio sucks (for me) and job sucks, so as soon as my lease ends in august, im out.

chicago

i’ve never been to chicago. i’ll visit in june to check it out. i also don’t know anyone there. this isn’t a huge deal since i have done this kind of move (only visiting right before moving and not knowing anyone) i guess 3 times now.

reasons i think i will like it

liberal city

great public transit

big, dense city

diversity

seemingly decent cost of living

people say midwesterners are friendly (?)

job opportunities just by the fact that it’s such a huge city

things that are/may be negative

brutal winters. i am not used to real winters. seattle/portland had very mild winters and even denver’s were honestly not bad at all. i hear lots of talk about chicago winters.

crime. no, i don’t think i will be regularly mugged or killed like the US media makes it sometimes seem, but compared to everywhere i’ve lived before, it’s has a higher violent crime rate.

friends/community. i’m in my mid 30s and it’s harder to make friends the old i get and that’s sort of my number one goal each time i move to a new city. also never really had “community” and would really like to have that in my life.

politics. i know that portland is generally much more left and chicago is more generic democrat. this isn’t the end of the world and i don’t expect everyone to be as far left as i am but i want to be able to live in the same reality as my community.

huge wall of text, i know, so thanks for those that read it. i’m not great at organizing my thoughts in these posts, but i’m just tryin’ to figure stuff out!

if anyone has anything they want to share based on my likes/dislikes and your experience, please do! i really enjoy reading what the folks here have to say about things.

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