Requesting your thoughts that may help me decide between moving to Chicago or Portland (Oregon)?
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.
Not helpful noise: come to Minneapolis and split the difference!
Further unhelpful noise: just leave the United States altogether and come up to Canada, where you'd have smaller cities and fewer opportunities, brutal winters anywhere outside of Greater Vancouver, and ridiculous housing costs from coast to coast to coast!
Minneapolis/Saint Paul is basically Edmonton with a slightly smaller ridiculously big mall.
Ours is about to get bigger though not sure it’ll beat Edmonton still though. We are adding an indoor water park and convention center
Where? That gravel parking lot north of the mall and east of IKEA?
Yeah, north side between the current mall and the highway. Big surface lot there. I don’t know all the specifics though.
In the past decade they did also build out an extension to the mall in that direction, too. Added the first directly connected hotel and an office tower. And a bigger food court. That food court is largely empty though— kinda just waiting to be connected to something larger.
Sorry for late response, didn’t notice I had something in inbox.
That partially explains why the Twin Cities is up there on my list to visit / move to, in an alternate universe.
i spent a few hours a few weeks ago pretending i’d move to montreal, actually! i’ve been watching a lot of youtube on urban cycling and public transit…
hey, this was actually a city on my list! i’ve actually been there once for work. but isn’t it even colder than chicago??
Here’s my favorite tool for comparing weather between different cities: Weatherspark
But the answer is: yes, Minneapolis has colder & longer winters than Chicago.
Personally, that’s not a big deal to me having grown up in the Twin Cites. I similarly moved away for a year and faced a similar choice of “I want to leave where I am and want to stay where I go next for a while.”
I couldn’t be happier that I moved to Minneapolis. But I understand the weather isn’t for everyone. And I do wonder about Chicago sometimes.
oooh thanks for the link, that’s very handy!
I love Chicago and I love Portland. I am a Cubs fan through and through, I grew up a few hours away, and I now love living life in the Willamette Valley.
The thing I always tell folks before they move here is that the grey is not as bad as you've told, but it's the biggest thing to complain about. Chicago (and the rest of the Midwest) are as grey for as long and colder. Now me, I miss the cold and snow, but I get why people don't like it. In general, if you didn't like the grey winters in Oregon, you'll have difficulties most places north of Texas and east or the Rockies, because those places will be similar, they're just depressing enough in other ways that folks don't complain about the skies!
However.
You've tried Oregon. It has not captured your soul. That's okay. My experience in the Midwest was flavored by rural isolation and incredible flatness of landscape and societal perspectives. Maybe it's not as gray as I remember? Certainly, Chicago is an AMAZING city for summer and autumn, incredible food, and abundant options for culture and travel that you may find in parts in Portland, but which will be fully at your beck and call in Chicago.
You can't always get things right when you try something new, but what you can do is make new mistakes. That's growth. Go make a new mistake. Go live life and love Chicago. You can always move again :)
i like your perspective and that’s actually a bit comforting to read so thanks for that!
i always thought (and still think!) i’d “end up” in portland again, i just don’t know exactly when that will be. i love the PNW, even if i don’t live there the majority of my life :)
I haven't lived in Chicago but I did go to university in Illinois, visited Chicago plenty of times, and have friends that now live in Chicago. I do think it's smart to visit Chicago to see if you'd like the city. If you've got the time + money, getting an Airbnb for ~2 weeks to a month would help you get a feel for things. I'm pretty biased here but I do think Chicago would be a great choice. Chicago is in a great place for American cities at the moment. You get a lot of the density + public transit that people adore about NYC and other real dense cities but you also get much lower cost of living compared to other big cities. It's also extremely walkable and bikeable (perhaps moreso than Portland) as the city is as flat as a pancake and in a nice grid.
I do think weather is Chicago's main weakness. Winters are pretty cold and summers are hot and humid. Even now, as we're supposed to be exiting winter and entering spring, Chicago weather is all over the place, bouncing between mid 30s to mid 60s in temperature and going from sunny to rainy. Given that you're moving out of Texas, you might've experienced similar summer weather so it won't be too much of an adjustment but the winters can take a while to get used to. Just make sure to layer up and wear proper snow boots.
Within downtown and adjacent neighborhoods connected to the L, crime should be fairly low. My friends have lived in Chicago now for 3 years and have never really had any issues with it, they're in the River North area though. Even in my many visits, the city has felt safe, including the L. There'll almost certainly be some characters on your trains in the late evenings but if you apply common sense, you'll be fine.
I can't speak on making friends and finding community in Chicago since I never lived there but I can speak a bit on the politics there. Chicago, in my limited experience, is more pragmatic and coalition-based in its political culture. It's certainly still a left-leaning city but it is more politically diverse and you'll find more variation in viewpoints even within left-leaning groups. I think people are more willing to compromise on certain things to get other things done. From my experience being from and living on the west coast, the west coast cities (SF/LA/SEA/PDX) do tend to be more ideologically cohesive and culturally progressive. Portland especially is ideologically consistent as you noted and very activist-driven, which is why certain news outlets like to focus on it so much. Values around social justice, climate change, identity, etc. are widely shared and openly emphasized in your day-to-day.
I love Chicago and have visited many times, but I grew up in the Midwest and so I'm used to the summer humidity and the brutally windy winters. I echo that the weather can be really rough if you're not used to it, especially if you're coming from Texas! Illinois does not have a lot of trees generally, and so it can be brutally windy and cold, and there's not much refuge from the sun in the summer. I strongly recommend a visit before choosing to live there - I love the look of Rust Belt cities (feels like home), but it is definitely not for everyone.
Another consideration that I haven't seen mentioned yet - Chicago has some of the worst traffic in the USA. The city is huge, and I have had friends living in the suburbs that had a two hour commute one-way. People also drive like total maniacs, but that's true of a lot of places. If you are planning to move there, you'll want to think pretty hard about what neighbourhood you want to move to and the COL - I was looking potentially at working in the city and a lot of housing has extra fees that drive the rent up a bit.
the traffic situation was something i thought about but just assumed id get rid of my car.
the rent prices vary an extreme amount depending on what part of Chicago im looking at, so it’s been a wild ride trying to pick out neighborhoods. i haven’t found a job there yet and would be working remotely initially/temporarily at my current job so it’s hard to plan what area i’d live right now this far in advance.
i’ve lived away from texas for 12 years minus this year so i did get accustom to milder weather. i’m a glutton for heat though
wow thanks for taking the time to write such a lengthy reply! i appreciate all the info and definitely agree about staying there for say 2 weeks to get a feel for things — i think that’s what i’ll do in july.
no problem, glad to help!
one risk of chicago is that the city is in a super fucked-up financial situation due to previous mayors doing stupid things for short-term gains, e.g. they sold off all their street parking and have massive unfunded public pension liabilities. From what I can see online the general consensus is that there will be a crisis of some sort in the near-term future, which could lead to mass strikes. If they don't figure out a way to declare bankruptcy there might just be very high taxes for poor services. OTOH these problems are all solveable, see e.g. NYC in 70s and 80s
Not sure how relevant this is over the next 5 years but might be useful to be aware of
this is good info to know and look into further. thanks for pointing it out!
I've lived in both but not sure the details matter too much, it sounds like you want Chicago. If you don't like the rain, and your love of the color green doesn't dramatically outweigh your dislike of grey, you don't want to live in the PNW.
Climate change might change things up, but that would be a gamble.
i’m interested in the details if you think it’s worth sharing!
Alright, a few details... Portland is significantly more liberal/progressive than almost everywhere. If that's a major factor Portland wins.
Portland is arguably a more beautiful city, especially in terms of the setting. Chicago never struck me as a particularly aethetically pleasing city. At the same time Portland has spent most of the last 10 years losing the battle with homelessness and public drug use in downtown. It's finally starting to turn around but it will be a while before downtown has fully recovered. Portland had a crime wave that's breaking to some degree. Despite that it's still the safer of the two cities statistically. Once upon a time it was one of the safest cities in the country, time will tell if that will come back.
Chicago wins in most of the "real city" ways. Bigger, more options for most things, denser, better walkability. Cost of living is comparable, housing in Portland is a bit more affordable but Portland has been catching up fast. I personally think Portland is very walkable/bikable but the river and bridges do spread things out. Public transportation is just ok in Portland.
If you like weird, Portland wins. If you like the traditional city vibe, Chicago wins.
i agree with everything you said about portland but also have always wanted to live in a big dense city. its so hard to choose!
Assuming you're planning on living within or close to the Loop and not like out in the suburbs, I'd go with Chicago. Bigger, denser city, with more residents who walk. If you're looking for community, IMO people are much more receptive to hanging out after work when they don't drive through miserable traffic both ways, and when entertainment and restaurants are another miserable drive in traffic away.
the quality public transit and hopefully living car-free for the first time in my life is an exciting thought.
It certainly is freeing to live car-free. No more having to worry about registration, gas/charging, parking when you go somewhere, parking at home, driving in traffic, etc. You just check the train schedule and work around it accordingly. Chicago is very easy to live car-free in. The CTA (local subway) and Metra (regional commuter trains) do have their issues but it's a solid system all in. If you ever do need a car, it's far cheaper to rent one through ZipCar.
I grew up in the Chicago suburbs and now live in the PNW. After living here for almost 10 years, I can safely say I'm never moving back to the Midwest. Primary reasons:
Given what you described in your post, it sounds like you have a different set of priorities that may better suit you for Chicago living than it did me. If you're planning on living in Chicago proper rather than the suburbs, like any major city, there's good areas and bad areas. You'll be able to find a spot that suits you and there's much better public transit, especially if you want to live in the city proper. Chicago has a great food scene (though I've also always loved Portland's food as well), and there's no shortage of activities in the city proper.
I think while Chicago/Midwest isn't for me, it might be worth a try for you. Maybe give it a short stint and see how you vibe with it and then decide if you want to be there long term.
thank you for the lengthy reply!
the outdoors/mountains/green will be hard to leave behind… like someone else said, i think portland is a beautiful city. while i sometimes hated the gray and drizzle, i did love that it never got below freezing often or mountains of snow. i love the heat so that doesn’t matter in either location (though i was around for that heat dome in the PNW and that was truly crazy. 114F!)
it’s really weird, some days i’ll be dead set on moving to chicago then ill read something or see a video about PNW/portland and i’ll get a homesick (i guess?) feeling.
so hard to choose!
Where did you grow up originally? And did you like where you grew up?
i grew up in and around houston. i’ll likely have to move back in the next 10 years for aging parents but otherwise would not ever want to move back. i liked the food options and museums but otherwise did not like houston at all. i also haven’t lived there in 12 years so im sure things have changed.
Gotcha. Some follow-ups:
before covid, i traveled within the states pretty regularly and internationally every other year. since then, i haven’t travelled internationally at all and only travel around the country maybe twice a year
i’m not an outdoor enthusiast (never hiked growing up in texas, didn’t in denver either) but at the same time i did hike nearly every weekend in the summer in the PNW for the last 3 years i lived there.
thinking based on my financial situation right now i’d put the limit at $1800 right now, may wiggle to $2k if it was a dope location and i could for sure sell my car.
don’t know if this matters to your advice but i have a cat and would like to get a dog very soon.
Initially, I was going to say Chicago might be a better option (bigger airport, cheaper housing, better transit), but given your responses elsewhere, and your friends in Seattle, I think Portland might be a better option for you.
Here’s a follow-up hot take: Could your parents move to Portland? Do they have an existing house in Metro Houston they could sell and use to purchase a place in Portland with you in the main house and then in an ADU on the property?
I’ve thought about having them move to me but they’ve stayed in texas so long because of my brother’s kids. Though in 10 years they may live elsewhere either for college or otherwise.
Chicago beats almost everywhere in the world for food and museums. It really is great. Not everything is perfect, but it really can be very nice. You definitely miss out on the great outdoors of Portland, but Portland misses out on the beaches and weather of Chicago, reportedly.
food is really important to me so that is something i’ve been paying attention to!
I've never been to Chicago and while I never lived in Portland I have family and interests there so I stay very connected with the city, even considering it a second home at times.
But I don't want to comment based on the locations, most other people here have already done very fair comparisons, however I do want to address your life situation and some of the things you've said you wanted.
I just turned 40 and spent my late twenties and thirties making big moves. I'm finally five years in at one spot, the longest I've lived anywhere since I left my home town and it's both comforting and restless at the same time.
You say you want friends and a community. You have friends already in Seattle and that is a very easy and convenient train ride from Portland to Seattle, to indulge those car-free desires a little bit. Since you already lived in Portland do you maybe have social connections there still or were you able to get a grasp on how the social scene is, where to maek friens or find ways to cnnect with people?
Both you and I are the same age demographic and, like you already said, it does get dramatically harder to maek friends in your thirties, especially once people start having babies. You have to ask yourself if the potential for friends and community outweigh your desire to live in a really big city and if Portland makes having that easier then I would safely say it outweighs Chicago.
If you are going to move back to houston in the next ten years then it makes more sense to me to choose which city will give you the most return in those ten years, whatever that return may actually mean. If Portland offers you a more stable base then it might be the worthwhile location. Not to give you a complex but time is short so make sure you choose wisely, I'd hate to try a new city and find that I wasted five years of my life looking for the wrong things. Having said that (!), life is short so if the idea of trying that big city life is something you think you'd regret later on, then go for it and don't look back - even if it didn't work out at leat you tried.
Sorry those two messages are so contradictory but if you can figure out what you want and what's important to you then one of those choices will clearly win out over the other.
When I was in my twenties and very early thirties I really wanted to live in a big city. I now find myself in a city very not unlike Portland in landscape, size, and entertainment opportunities and I'm very happy to be here at this age. A part of me regrets not having lived the big city life but I realistically know that that was a dream for a younger me, I still like to visit the huge cities but I don't know if I'd want the stress that comes with actually waking up there every day. At this point in life the medium size of a city like Portland gives just enough of the big city flavor (just a taste really) to satisfy the day to day and the rest I make up for with visits. And hey, the big town feel that comes with a city like mine or Portland can often lend itself to a real sense of community.
thank you for the thoughtful reply. what you’ve said really resonated with me and i think i’m getting a clearer picture of what i want to do now.
i think i’ve just gotten used to chasing the shiny new thing (a new city/life) but am really just looking for Home. i love portland and think its as close to that as ive got so far in my life.
its so refreshing to see so many people actually read everything and give meaningful replies :)
I was born and raised in and near Chicago and lived there until ~5 years ago when I moved to California. I say that to give be upfront about my biases: I love Chicago and its people and if I have the opportunity with my career to move there again I absolutely would (giving up this beautiful California weather in the process)! I think it's the greatest city in the country. It seems like other people have responded to most of your points and I'm not sure I have much else to add, but I'm happy to answer questions if you have any. My only advice is that when you visit, make sure you get out into the neighborhoods and don't just stay in or around downtown! In no particular order, all of the following are beautiful and have their own unique character and vibe, some more than others:
Happy to get more specific. This list is heavily biased towards the north side but those are the areas I'm most familiar with; my impression is that they are also the areas most transplants move to.
Pilsen and Logan Square are my top picks to check out apartments!
I’ve lived in DC, NY, LA, Chicago, Denver and Austin.
Having friends or family in a place has always been the biggest determining factor for me in how much a place felt like home. So that’s a ‘plus’ for Portland. If you’re good at meeting people (or likely to meet a significant other and sort of adopt their group) I’d discount this a bit. But I lean introverted, and that being the case, in your shoes, I’d think hard about whether Chicago is going to be another city I don’t set roots in.
I’d also ask myself if earlier time in Portland promised enough community to make it worth returning to. (On that note, I’d consider Seattle if you already have good friends there. Sure cost of living is horrible, but I lived in New York in my 20s on a nonprofit salary and had a great time because I had a community of friends with similar circumstances.)
Agree that making friends seems tougher as one ages. An exception to this seems to be if you have kids. It’s an easy opportunity (though not guaranteed) to find a new community. So if this is in the cards for you regardless of destination, that’d be another factor to make me discount the Portland a little (as it implies solid community opportunities in Chicago).
All those issues aside, I really enjoyed Chicago. When I was there roughly 10 years ago, there were plenty of relatively affordable apartments on Lake Shore Drive with views of Lake Michigan. I can’t overstate how much I loved my view of Belmont Harbor. It made me feel a bit more connected with the outdoors just looking out that window. Plus it was easy to get across the street to the trail and run or walk. Even in bad weather. And as others have noted, there’s lots to do.
i lived in seattle for 7.5 years and while i did enjoy most of my time there, i don’t really have any interest in moving back unless i got some kind of “dream job”.
the first year of living in portland was truly the best time
of my adult life but then the last year, or really last 8ish months, was very, very bleak (job, money problems, mental health crash).
i’m pretty introverted but do enjoy trying to make friends as long as it’s one on one. friends/community is probably the most important thing for me nowadays. i don’t think ive really given it the importance it deserved in the past as i sort of just made friends without trying too hard but they weren’t the deep connections im actually seeking. i’m a single dude with no interest in having my own kids but am interesting in dating. i date all genders but it seems like that wouldn’t be a problem in chicago (i think?) and it didn’t seem to be in portland.
while it has been kind of nice being in close proximity, i’m not super close with my family, so visiting once or twice a year works for me.
honestly if money wasn’t a factor, i’d move to nyc or san francisco without hesitation. it’s just that money is absolutely a factor…
I don't know if this is meaningful for you, but Chicago has an extensive LGBTQ+ scene that's got more formal stratification than Portland. My friends say there's something for everyone, from cheap coffeehouses to leather and drag bars to posh clubs. [I make a point to visit the extravagant sex toy stores while I'm visiting.]
You'll find any cuisine you can name and some you've never even dreamed of. Like most big cities, Chicago is a wonderland if you're not short on funds.
However, there is a substantial homeless population, mostly chivvied away from the wealthy downtown areas. You won't drive through an underpass without seeing huddled humans in suffering and misery, taking shelter where they can.
If you're interested in occasional hiking, you can reach the best parts of the western Michigan shoreline within a couple of hours drive - forested state parks with good trails, moderate hills, and camping/biking/boating/snowmobiling/skiing amenities.