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Well, I worry that Chicago will be too much of a stressful hard city and chew me up and spit me out, BUT I don't see Portland being like that.
I'm a transplant from Iowa going on 17 years in Chicago. The spirit and lifestyle in Chicago is definitely NOT one to chew someone up and spit them out. Certainly not like the stereotype might be for New York. There really isn't this competitive drive to succeed in Chicago and compare yourself to your peers and everyone else. There's a drive to have fun, party, meeting people and relax. Going to parties and bars you focus on having fun, not what to wear. It's more a city where you try to be you and be fine with whatever that might be, not really as much trying to fit in.
There's that uppity class and group who certainly thinks like that in the city, but they don't control the entertainment or bar scene. If you don't feel like being a part of that scene and mentality, just go focus on the majority of the city and social scene that doesn't bother for any of that. Life and let live, no one cares what you do. I've never found it to be a very judgey city.
Factors to consider:
-Easy place to make friends
-Affordability
-Settling down and getting an organized balanced life (would ideally live there for 10 years minimum)
-Easier to live without a car
-Steady work in the sound and video field (I have experience in both events and permanent install)
-Better place for dating
-Cheap dive bars
-This one is a long shot but a bigger cosplay community. I cosplay Kylo Ren so the city with more events to do that would be nice.
never been to Portland or the Pacific Northwest but I'd probably love it as the scenery looks so gorgeous and the weather stats are phenomenal, so these comments are exclusively about my 12 yrs in Chicago.
-friends -- yes -- you can meet a lot of friends in Chicago but at the same time it can also be very transient. Most of my closest friends I've met here have actually moved elsewhere, but the flipside to that is that Chicago is centrally located so travel to just about anywhere is amazingly easy. I'm going to be going to LA in a couple of weeks to visit 4 of my closest friends, 3 of them I met here. As I finish grad school and have to navigate the whole career question, I myself may/may not stay here but 12 years does meet your barometer.
-affordability -- super affordable, especially without a car. If you really want to get insanely affordable, keep it to studio apts. Also low-key check out Rogers Park/Edgewater. They are transit connected, but more travel time. However they are affordable, diverse, and surprisingly scenic as they are right along the lake. Super intellectual/creative vibe also.
-steady work in sound field -- IDK about that specifically but in general Chicago is an economic powerhouse with many strong sectors. People move here for the combination jobs + affordability.
-dating -- this for me has been the surprisingly toughest aspect, though I may be the outlier. Commenting on gay dating only but many of the same dynamics such as a ton of activities, bars, events, volunteer opportunities, etc to meet people are the same regardless. I've met quite a few guys but have had the worst dating luck ever . . . but a lot of people do quite well here. Another theoretical plus is that this is a decent logistical place from which to distance date -- my former boss dated someone who lived in LA for like 4 years and they just flew back and forth; another person I know dates someone who lives in Atlanta, which is like an hour to an hour and a half flight. No need to drive + high concentration of people + affordability theoretically should = lots of opportunity. LOL I should be out now but my bball league starts tomorrow so I need to be sober!
-Cheap dive bars -- ABSOLUTELY YES! All over.
-Cosplay -- IDK but there is a huge C2E2 comic book fest so that may be up your alley.
Even though this is a huge city, large swaths of it have a mainstream Americana/midwest vibe/feel FWIW.
As someone who has lived in Portland before and now living in Chicago. Making friends in Chicago is easier, compared to Portland, which has a very introverted, cliquey, vibe. Look up "Seattle Freeze" as it applies to Portland. Chicago is more affordable than Portland. Cost of housing in Portland is higher, while wages are lower (except for maybe tech?). Chicago is easier to settle down in as it has more affordable housing options and much more career opportunities. Chicago is much easier for car-free living. Portland's buses and street car are very slow. Their MAX light is more like a commuter train. Dating scene is better in Chicago, unless you are into the very grungy, gronola, hipsters. Also due to the passive aggressive nature of Portland, dating has many challenges. Not many attractive women in Portland, so many 5s-6s act like they are supermodels and the few 7s there....oh man really bad attitude.
Quote:
Originally Posted by simon22
I'm a 33-year-old single heterosexual male.
Factors to consider:
-Easy place to make friends
-Affordability
-Settling down and getting an organized balanced life (would ideally live there for 10 years minimum)
-Easier to live without a car
-Steady work in the sound and video field (I have experience in both events and permanent install)
-Better place for dating
-Cheap dive bars
-This one is a long shot but a bigger cosplay community. I cosplay Kylo Ren so the city with more events to do that would be nice.
As someone who has lived in Portland before and now living in Chicago. Making friends in Chicago is easier, compared to Portland, which has a very introverted, cliquey, vibe. Look up "Seattle Freeze" as it applies to Portland. Chicago is more affordable than Portland. Cost of housing in Portland is higher, while wages are lower (except for maybe tech?). Chicago is easier to settle down in as it has more affordable housing options and much more career opportunities. Chicago is much easier for car-free living. Portland's buses and street car are very slow. Their MAX light is more like a commuter train. Dating scene is better in Chicago, unless you are into the very grungy, gronola, hipsters. Also due to the passive aggressive nature of Portland, dating has many challenges. Not many attractive women in Portland, so many 5s-6s act like they are supermodels and the few 7s there....oh man really bad attitude.
nice to have the perspective of someone that has lived in both cities
For me the obvious choice is Portland, if only because of the summer weather.
Portland will be beautiful, sunny and only in the low 80s, with little or no humidity, and no wind.
Chicago will be a bit higher to much higher, 80-92, but averaging 68% humidity.
Portland does have dive bars, and in fact, the 2nd most strip clubs per capita in the country, behind Houston.
... Except when it isn't. Portland usually runs about 5 degrees warmer than Seattle in the summer and always seems to be 85-90 when we go to visit. I went and looked back at the temperature graphs for the last few years and it turns out that wasn't just my imagination.
... Except when it isn't. Portland usually runs about 5 degrees warmer than Seattle in the summer and always seems to be 85-90 when we go to visit. I went and looked back at the temperature graphs for the last few years and it turns out that wasn't just my imagination.
Thanks for this. When I was in Portland it was hot as well, and really didn't know if that was normal or just a fluke. I do know that Chicago summers are great by the lake, and the comment that Chicago summer's aren't is really untrue.
LOL I don't think strip bars are cheap ..... Nor strip mall bars ....
Portland has a ton of cheap dive bars that are neither strip clubs or in strip malls. Obviously Chicago is on another scale and is probably the best dive bar city in the country, but Portland is a great dive bar town. (Also worth noting that many “strip clubs” in Portland are just dive bars with a stage and strippers.)
Factors to consider:
-Easy place to make friends
-Affordability
-Settling down and getting an organized balanced life (would ideally live there for 10 years minimum)
-Easier to live without a car
-Steady work in the sound and video field (I have experience in both events and permanent install)
-Better place for dating
-Cheap dive bars
-This one is a long shot but a bigger cosplay community. I cosplay Kylo Ren so the city with more events to do that would be nice.
- The PNW is not known for the best place to make friends. I lived in Seattle for four years and I enjoyed it but the Freeze is real. Chicago is better to meet new people.
- Portland is not cheap. Chicago isn't cheap either and Illinois is ridiculously taxed, especially property taxes.
- Portland has often been known as a "Bring your own job" city. Although I have heard tech has been doing pretty good there the last couple of years.
- Chicago is a better place for dating.
- You can live without a car if you live in the downtown area of Portland especially the west end, although I would still want one. Chicago hands down in the comparison.
I like your last question, Portland has brought down some of the cool "Portland Weird" vibe, it's been heavily gentrified, although I would say it would be better than Chicago in that category.
Why those two cities? They are totally different and Chicago is huge in comparison. At your age I would consider Austin, it will not have the live without a car condition you want. But if you want to go were the "Hot Girls" are it's miles above Portland. I hope I am not offending anyone, there are pretty women in Portland as well but in terms of quantity Austin slays it.
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Nor strip mall bars .... 
