Portland vs Chicago

[marothisu]

Originally Posted by phalanx

- Portland is not cheap. Chicago isn't cheap either and Illinois is ridiculously taxed, especially property taxes.

Property taxes in the Chicago area are pretty high. Though consider that the income taxes in Oregon are a lot higher than Illinois. Currently, there is a 4.95% flat tax for income in Illinois. Oregon on the other hand, you'd basically be taxed at 9% at a minimum for your income (5% if you almost made literally nothing all year). All things considered, if you owned property in either with the income tax differential things could basically become a wash.

For the type of city that it is, Chicago is not that expensive all things considered - compared to other places of similar type of capabilities (i.e. public transit, walkability, culture, etc).

Of varying levels of price...
* Portland - $330K for a 1 bed/1 bath 734 sq ft condo downtown. https://www.realtor.com/realestatean...5_M22451-64497

* Chicago - $330K for a 1 bed/1 bath 840 sq ft condo downtown. https://www.realtor.com/realestatean...1_M75618-49022

Around $750K
* Portland - $765K for a 2 bed/2.5 bath 1798 sq ft condo in Nob Hill. https://www.realtor.com/realestatean...0_M10061-14952

* Chicago - $750K for a 3 bed/2.5 bath 2500 sq ft condo in Wicker Park. https://www.realtor.com/realestatean...2_M79306-88948


Over $1M
* Portland - $1.388M for a 2 bed/2.5 bath 1909 sq ft condo on the river. https://www.realtor.com/realestatean...-94197?view=qv

* Chicago - $1.2M for a 3 bed/2 bath 2150 sq ft condo on the lake across the street from a beach (with the lakefront view) essentially downtown. https://www.realtor.com/realestatean...0_M81651-21472

[Minervah]

Originally Posted by simon22

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.

May I ask why you don't see Portland being like that and Chicago as being so? Are you going from personal experience or hearsay?

I can only say that, going by my experience, as one who has lived in both, I believe the opposite is true. I am not knocking Portland but one must be strong to survive there especially the first few years. It can be more lonely than many other places including Chicago.

In Chicago, due to its much larger size, it is not all that difficult for someone to find others with similarities enabling them to fit in, and people are more friendly in general. In Portland, if you don't fit one or two fairly standard molds, you could wind up becoming lonely and depressed.

If you do choose Portland, just be prepared to work hard at making a satisfactory social life for yourself.

[CityPlanning]

I have lived in both and overall tax burden is probably a wash. Cost of housing I do feel is slightly higher in Portland for comparable neighborhoods. If you compare River North Condos Vs. Pearl District condos you will notice that price per sf is higher in Portland's Pearl District and not a single building there has a swimming pool!

They are very different cities due to size and with Chicago having much more dense/vibrant neighborhoods, but I guess here are comparable neighborhoods:

River North (Chicago)- Pearl District (Portland) - Actually Peal District is a hybrid of River North and West Loop. This is where the snobbiest Portlanders live and many of the new developments there are selling for million +. Even some residents there compare that area to a Manhattan neighborhood, which is laughable. The area is very quiet after 11:30 pm even on weekends. I hear its the NIMBYs there that complain about noise which I don't understand if they want to live in downtown? Nightlife there is in adjacent Old town/Chinatown, which is a gritty area with very bad homeless problems and the scene is trashy suburban kids going "downtown". It Lacks upscale nightlife venues that River North offers. https://www.kgw.com/article/news/inv...51796491599416

Gold Coast/Rush/Division (Chicago)- NW 23rd/Nob Hill (Portland)- NW 23rd is considered the sport where Portland's wealthy from the West Hills shop and dine. The area is very dead 10pm on weekends since there are very few bars on 23rd. Bars are on 21st, which has a weird scene of hipster meets post OSU/UO
frat boys, however after 2012 the nightlife there is pretty much died.

Wicker Park (Chicago) - Inner SE (Portland)- Kinda....Inner SE Portland is much more granola, white, and extreme hipster than Wicker Park.

Logan Square/Bucktown (Chicago)- Inner NE and Nopo (Portland)- Well over 10-15 years ago some would say that NE and N Portland would've been comparable to the Southside or Westside....but in reality they were never ever that dangerous, but for Oregonians it was considered very scary because that was the only area in entire Oregon where you would see black people. The area rapidly gentrified in 2000s and now now its one of the hippest place for hipster transplants.

I think Portland these days is very overrated and insanely overpriced, while Chicago is undervalued for being a world class alpha city. If you value urban/cultural amenities, nightlife, vibrancy, Chicago is a clear winner. If you value outdoorsy things, want a slow pace of life, then Portland wins. Also another factor is that besides tech, wages in Portland are lower than Chicago, especially in finance/accounting/marketing fields.

Originally Posted by marothisu

Property taxes in the Chicago area are pretty high. Though consider that the income taxes in Oregon are a lot higher than Illinois. Currently, there is a 4.95% flat tax for income in Illinois. Oregon on the other hand, you'd basically be taxed at 9% at a minimum for your income (5% if you almost made literally nothing all year). All things considered, if you owned property in either with the income tax differential things could basically become a wash.

For the type of city that it is, Chicago is not that expensive all things considered - compared to other places of similar type of capabilities (i.e. public transit, walkability, culture, etc).

Of varying levels of price...
* Portland - $330K for a 1 bed/1 bath 734 sq ft condo downtown. https://www.realtor.com/realestatean...5_M22451-64497

* Chicago - $330K for a 1 bed/1 bath 840 sq ft condo downtown. https://www.realtor.com/realestatean...1_M75618-49022

Around $750K
* Portland - $765K for a 2 bed/2.5 bath 1798 sq ft condo in Nob Hill. https://www.realtor.com/realestatean...0_M10061-14952

* Chicago - $750K for a 3 bed/2.5 bath 2500 sq ft condo in Wicker Park. https://www.realtor.com/realestatean...2_M79306-88948


Over $1M
* Portland - $1.388M for a 2 bed/2.5 bath 1909 sq ft condo on the river. https://www.realtor.com/realestatean...-94197?view=qv

* Chicago - $1.2M for a 3 bed/2 bath 2150 sq ft condo on the lake across the street from a beach (with the lakefront view) essentially downtown. https://www.realtor.com/realestatean...0_M81651-21472

[Radical347]

Based on your criteria, Chicago is better for everything except cosplay community. In Chicago it’s still pretty decent and you’ll find what you need, but for cosplay and general geekery Portland absolutely slays and no other place is close (Seattle would be 2nd.)

[Shakeesha]

Easy place to make friends: Chicago
-Affordability: Chicago
-Settling down and getting an organized balanced life (would ideally live there for 10 years minimum): Chicago
-Easier to live without a car: Chicago
-Steady work in the sound and video field (I have experience in both events and permanent install): Neither are media meccas, but Chicago is moreso.
-Better place for dating: Chicago
-Cheap dive bars: Chicago
-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.- Portland

I would definitely choose Chicago. Chicago offers the best of both worlds. There is a large working class as well as upscale wealthy areas. Most Chicagoans are very sociable. They are extroverted, but not in an annoying or pretentious way that you might find some other midwest metros. Chicago is diverse and offers many opportunities for career development (if you are serious and work hard).