Portland and Chicago: Observations After Living In Both Cities

Alisa Hauser
Feb 21 · 11 min read
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l-r: Blu outside Lubinski Furniture in Chicago, December 2018, and in Forest Park in Portland, December 2019

PORTLAND — I relocated from Chicago to Portland in December 2018.

If you’re thinking of making the same move — or are curious to know some differences between the Pacific Northwest’s “City of Roses” and the Midwest’s “Windy City” — here are a few observations.

Feel free to add your own insights.

  1. No one honks in Portland. Drivers are tentative. They will stop their cars if a pedestrian is spotted even at the last second.

In Chicago, pedestrians and cyclists don’t expect any moving vehicle to stop for them. And if you’re driving, the driver behind you will honk if you don’t turn fast enough or are moving too slow. Are people not in a hurry here? Are they worried about being impolite? I live with a former Chicagoan who shows no qualms about honking — though the frequency has subsided the more he realizes no one else is honking here.

One local man says he can tell the “domestic foreigners” because they press down on their car’s horn for more than a few seconds… and use umbrellas. (It does rain a lot in Portland, though the true locals prefer hooded raincoats).

A Portland native talks about how to tell if a driver is not from Portland.

2. Hand Car Wash ‘Desert’. Unlike Chicago, where there seemed to be a hand car wash every few blocks, there is only one place that I know of within a short drive, and it’s usually very busy.

Perhaps there are fewer hand car washes here because there is no salt on the road, to gunk up exteriors? Or people just like the satisfaction of washing their own cars? There also seems to be a lot of single-family homes in Portland, increasing the likelihood of having a driveway to wash a car in.

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Armando washes his car in his family’s driveway in Portsmouth, a North Portland enclave.

3. Love Thy Bridges. Though Chicago actually has more bridges than Portland (42 operable bridges vs. 12), you don’t seem to hear about bridges as much in Chicago unless you have a bridge fetish.

Portland calls itself “Bridgetown” and its bridges are part of the city’s fabric, as well as directional icons to navigate Portland’s five quadrants (Northwest, Southwest, North, Northeast, and Southeast). Update, per someone on Reddit there are six quadrants now. Hello, South! Source: Willamette Week.

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The St. Johns bridge as viewed from Forest Park’s Ridge Trail.
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The Broadway Bridge over the Willamette River in Downtown Portland.
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The Tilikum Crossing Bridge opened in 2015 and is for public transit, pedestrians and cyclists only.
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The Hawthorne Bridge is one of the city’s busiest- just not on a Saturday night during a pandemic.
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How long will it take my friend Jessica White in Chicago to notice I lifted this pic from her Instagram? (Update: an impressive 10 minutes!!)

Whereas the bridges to get over the Chicago River are short in length and narrow — and not usually bike or pedestrian friendly — the bridges in Portland take a longer amount of time to get across and tend to accommodate more than just cars. A new pedestrian and bike bridge over Flanders connecting Portland’s NW District and The Pearl was installed at the start of 2021 and is expected to open in the spring, per a KATU report. (thank you Marc Thayer for the correction).

4. Strip Club Central. If you enjoy strip clubs, Portland offers many types of clubs, from those that strictly serve vegan fare (Casa Diablo) to clubs geared for tourists (Mary’s) and the local fave (Sassy’s).

Portland, which is much smaller than Chicago, boasts 54 strip clubs as compared to four in Chicago. According to research by Priceonomics, Portland has the highest number of strip clubs per capita in the U.S.— one for every 11.286 residents. That is mainly because Oregon’s constitution protects “obscenity” under the first amendment.

Portland’s fully nude strip clubs also serve full alcohol and food. In Chicago, if a strip club such as VIPs, serves alcohol, then the dancers cannot take off all their clothes. If a strip club in Chicago does not serve alcohol, it can offer full nudity and be open 24/7. Hmm. (Update: VIPs is now Rick’s, thanks for the fact check, @bMartini5 on Twitter).

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The Dancin’ Bare in Kenton is for sale; the owner blames the pandemic and forced closures. A sign in January 2021 apologies for clothing.

5. Bike Commuters Everwhere. Perhaps because the roads often have bike lanes and the weather is usually pleasant and the air feels clean, Portland ranks №1 in the country for having the highest percentage of bike commuters.

When I bike commuted in Portland pre-covid, I’d never seen more kids being toted home from school by parents riding fancy cargo bikes.

According to a 2019 Move analysis using U.S.Census data , some 6.3 percent of commuters in Portland ride their bicycles to work as compared to 1.7 percent of Chicago’s commuters. Without stating the obvious, Covid has likely dramatically altered these numbers.

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A commuter and his dog Shasta wait to turn left at the Broadway Bridge, winter 2019.
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This commuter rode his unicycle to the MAX station.
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A worker cleans a BIKETown kiosk, Portland’s Sponsored-by-Nike equivalent to Chicago’s Divvy.

6. Portland’s Cultural Pockets are Tighter/Less Inclusive to Strangers. In Chicago there were so many Ukrainians that there there were two outdoor Ukrainian festivals, somewhat competing and a few weeks apart in the summer. There was also Greek Fest, Taste of Polonia and so many more cultural festivals and events.

A few summers ago I went to a Ukrainian festival in a Portland park and felt like me and my friend were the only two people there that didn’t know anyone else. The event felt more like a large church picnic than a public festival.

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Dancing circle at the Ukrainian festival in Portland, summer 2019

7. Riots, Fires Giving Portland a Bad Rap. A few Portlanders — who do not represent the whole — sometime win attention for destroying things.

Check out this footage of New Year’s eve 2021 in downtown Portland. The damage was so bad a Starbucks may not reopen. Several big name corporations have already pulled their headquarters out of downtown. Mayor Ted Wheeler said at a press conference, “There are some people who just want to watch the world burn. This is what we’re up against.”

Speaking of burning, the Air Quality is mostly better in Portland than in Chicago — except during wild fire 🔥 season.

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The fiery orange sunlight reflected on Blu in this no-filter shot.
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The air was very hard to breathe in early September when fires spread through the West Coast and PNW.

8. Beer, Bar Food Better. Though Chicago technically has more breweries than Portland (167 vs. 139 based on a 2018 report) the craft beer options in Portland seems more plentiful — and bars are likely to serve predominately craft beers.

Since Oregon law requires any bar that serves alchohol to have food, there tends to be good food even at dive bars. A friend said what you eat at dive bars in Portland is similar to the food at “gastropubs” in Chicago.

9. Portland Less Diverse Than Chicago. Walidah Imarisha, an educator and black history expert, told The Atlantic in 2016 that Portland has in many ways “perfected neoliberal racism” and that the state’s origins as a racist white utopia is an ideology still in effect today despite being a politically progressive city. Read more in The Racist History of Portland, the Whitest City in America” by Alana Semuels.

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A sign in the window of a tattoo shop in St. Johns.

According to Best Places, which draws data from various sources including the U.S. Census, 5.6% of Portland’s population is black as compared to 30.1% in Chicago. Whites make up 71% of Portland vs. 32.7% of Chicago.

There are fewer Hispanic residents in Portland than in Chicago (9.7% of Portland’s residents are Hispanic vs. 29% of Chicago’s).

The only minority that is more prevalent in Portland than Chicago are Asian Americans, who comprise 7.7% of Portland’s population vs. 6.2% in Chicago.

If you want to be around diversity in Portland you need to live in a diverse neighborhood, such as Portsmouth, ranked #1 in diversity of Portland’s 86 neighborhoods and among the top 5% of America’s most diverse neighborhoods . Some 18% percent of Portsmouth’s 12,039 residents are black, 20% are Hispanic, and 53% white. Seven percent of Portsmouth’s residents are two or more races and three percent are Asian, source: Niche.com)

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A sign in a window in Kenton, a neighborhood next to Portsmouth.

10. Portland Wins At Curbing Waste! Gyms, at least the one I used to go to, had stacks of washcloths and antiseptic spray bottles instead of disposable wipes for cleaning down exercise machines.

Manicurists at nail salons will ask if you remembered to bring “your kit,” which is a buffer and nail file, part of a hygiene law that also reduces waste.

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A kit from OPI Nails in North Portland.

In terms of “freecyling”, people leave all kinds of stuff at their curbs for others to take and there are more consignment and thrift shops in Portland than in Chicago. “Buy nothing” Facebook pages are very popular in Portland, along with Little Free Libraries. According to the Little Free library map, there are almost 40 registered libraries within a few miles of my Portland home and just 9 near my former Chicago apartment.

11. Homeless People Acknowledged/Respected/Supported in Portland.

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A homeless person sleeping just before sunrise in Old Town/Chinatown, winter 2020.
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Formerly a Rite Aid, this building is now a severe weather shelter.
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Homeless camp near Hayden Island in North Portland.

A former Rite Aid in Kenton recently was transformed into a warming center and shelter for homeless people. On Nextdoor a few months ago, neighbors were praying for a Trader Joe’s in that building instead (similar to Chicago it seems). Homeless people in Portland seem much more welcome than in Chicago, perhaps due to their critical mass or more visible numbers? Almost every neighborhood has a camp or two and some even have sleeping pods or villages.

13. Odd Laws in Portland. Can’t pump your own gas! No hard liquor sold in grocery stores, which only sell mixes… This law is explained by Ben Elstein, who works in merchandising for a bike apparel company.

“Oregon has controlled liquor sales, historically, out of a paternalistic sensibility of protecting the public from its own imbibing inclinations. The often unstated practical outcome of this stance is a near total monopoly on liquor bottle sales revenue (and thus an ability to set prices) in a state with no sales tax for generating funds for public services….Since the state operates liquor stores, the state captures 100% of the profits those stores generate,” Elstein says.

Oh, urinating in public is allowed in Portland. Some new laws in 2021 include decriminalization of small amounts of recreational drugs as well as approving psilocybin or mushrooms for therapeutic use.

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Portlanders love putting out benches.
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If you like bumper stickers, Portland is a good place for you to drive around and express yo’self.

15. We’ll All Go Down Together. Portland and Chicago share one not so great fact: both cities are on the decline when it comes to the 2021 PWC Emerging Trends in Real Estate report.

Four years ago, in 2017, Portland was ranked the third most desirable real estate market in the nation. This year Portland ranked 66th of 80 cities. Read more in Willamette Week.

The decline of Portland is attributed to investors lack of confidence, media fixation on protests, and insurance costs rising as much as 50 percent due to repeated Downtown vandalism.

For its part, Chicago took a fall, though not as dramatic as Portland’s.

In 2017, Chicago was ranked 19th of 80 cities in desirability and for 2021 it dropped to 44th place. Sources, the 2017 PWC report, (page 57) and 2021 PWC report (page 36).

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Read the fully alarming story HERE.

16. Nature! Nature! Nature!

I wince when I think of how much I loved The 606 (recently renamed back to its original Bloomingdale Trail) and how magical it was for me, having no car and no way to escape busy streets unless I was on that 2.7-mile-long elevated oasis. While Chicago residents have The 606, as well as day trips to Starved Rock or the Michigan Dunes, in Portland there are mountains within a 90-minute drive, trails nearby including one a little longer than The 606 that I’m about to walk on if I ever finish this post. The concrete city of Chicago will never match Portland’s natural beauty.

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Snowboarding at Mt. Hood.

17. Chicago Skyline Forever. Portland has no Jeanne Gang. The goosebumps you feel while driving into Chicago from the Dan Ryan expressway and seeing the glittering buildings and lights, none of that really happens when you look at Portland’s skyline which is beautiful too, just jumbled and random with a mountain looking over it. I don’t think anyone moves to Portland for the architecture, but I could be wrong!

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Chicago in winter 2021. Even snow can’t damper this amazing skyline. [Photo by Susan Anderson]
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Audrey Wennink has been cross country skiing in Chicago. (Source: Twitter)
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So that’s about all I’ve got in major differences that stick out!

Some random photos of Portland are posted below.

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A bustling downtown, December 2019.
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Forest Park- one of the largest forested public park in America- is in Portland.
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Sauvie Island at sunset, summer 2021.
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Indigo Girls concert at the zoo, June 2019.
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Low Bar Chorale’s Holiday Show, December 2019, at Mississippi Studios.
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A barge carrying goods near Kelley Point.
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Smiley happy car.
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Heather’s fave place for Karaoke.
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Fall colors, November 2020.
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Oregon coast/Rockaway Beach.
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Rockaway beach.
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Blu on the beach.
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Proxy Falls.
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Mt. Hood as seen from the Interstate Bridge.
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Kenton’s iconic lumberjack statue all masked up.
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Mt. Hood
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Kelley Point Park, January 2021.
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Forest Park, February 2021 (photo by Dan Meier)
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Walking home through Forest Park…
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Columbia Park, February 2021.

The Pipeline

extremely sporadic posts from a former Chicagoan in Portland

Alisa Hauser

Written by

Portlander since December 2018. Former Block Club, DNAinfo and Chicago Pipeline reporter.

The Pipeline

in the space between journalism and blogging

Alisa Hauser

Written by

Portlander since December 2018. Former Block Club, DNAinfo and Chicago Pipeline reporter.

The Pipeline

in the space between journalism and blogging

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