8 ms·

It has always surprised me that Chicago's tech scene never really took off. I recently left (for a tech job), and it saddened me - Chicago is the best city in t

It has always surprised me that Chicago's tech scene never really took off. I recently left (for a tech job), and it saddened me - Chicago is the best city in the world from June-Sep. I really wonder why tech doesn't thrive there. Common diagnoses (crime, taxes, regulation) all undoubtedly make an impact - but none are as bad as SF/NY. And frankly, crime and taxes aren't really as bad as the news make them seem. Meanwhile, it has 3 top-20 tech universities, major employers, huge population, low COL, and so many things to do. What gives?

xhkkffbf 4y ago
It is a great city, but the tax rates are outrageous and they're going to get worse. Just look at the funding of the pension plans. Illinois and Chicago have some of the worst funding ratios. They've promised too much to workers and never set enough aside. There's a reason why companies like Boeing or Citadel are fleeing.
- colinmhayes 4y ago
  Boeing left because their tax break ended for what it's worth.
  - tptacek 4y ago
    Boeing was barely here to begin with. They consistently missed their job targets, despite being allowed to count contractors towards the anemic targets they were meant to hit. Citadel is a body blow, but Boeing? Who cares.
  - Kon-Peki 4y ago
    A few years ago the Citadel CEO went through a very public and extremely acrimonious divorce, during which the wife and kids left Chicago for the east coast and refused to come back. So now, he's all alone, and seemingly getting angrier by the day. His politics are increasingly distanced from what people in the area are interested in, etc. Moving to a location where he might see his kids more often might just make him a lot happier and less angry. If so, that's good for him.
- closeparen 4y ago
  In what way is Chicago’s tax situation worse than SF or NY?
  - eschulz 4y ago
    Illinois is generally in the bottom three of states for pensions being underfunded, and Chicago is normally the city with the highest or second highest sales tax in the US. As an Illinois resident I'm concerned about the high percentage of taxes over the next several decades that will go to service debt, and therefore not provide other services. I think this causes issues which scare away established employers as well as entrepreneurs (high crime rates, struggling public schools, etc). This will then drive away young people who are looking for good jobs, and therefore Illinois misses out on the taxes those people would pay over their careers and thus the situation spirals down further. https://taxfoundation.org/state-pension-funding/ https://taxfoundation.org/state-pension-funding/ https://www.taxjar.com/blog/cities-and-states-have-the-highest-sales-tax-rates https://www.taxjar.com/blog/cities-and-states-have-the-highe...
- curiousllama 4y ago
  This is a fair point. Long term tax issues could def be a factor. Even beyond the abstract potential bankruptcy: who wants to buy a house when 90-110% of appreciation will be eaten by the inevitable tax increases?
- tptacek 4y ago
  The tax situation is not great, but for tech workers, it ultimately just means that Chicago is not as advantaged over NYC and SFBA as it could be; the cost of living here is so much lower that it's hard for me to think of a scenario where you wouldn't come out substantially ahead. My kid brother is buying a starter home, in a relatively (obnoxiously) expensive part of Chicagoland, and to get the same house within an hour's drive of San Francisco he'd be looking at 4-5x the outlay. The property tax situation does mean that Chicago houses aren't mortal-lock speculative investments the way SFBA houses are, so there's that to contend with.
1123581321 4y ago
The venture money in Chicago is too conservative. It’s not a great city during the winter. There aren’t enough large, innovative employers in silicon hardware, or software. The state has latent brain drain due to taxes and a few other things. Source: have spent years trying to make it better. Edit: want to be clear that the money isn’t conservative in a good way, encouraging small, sustainable businesses. It’s reluctant to support those at a reasonable price as well.
- curiousllama 4y ago
  This is a new interesting point to me, which makes total sense. All the big $ in Chicago seem to go to prop trading, not VC. Combine that with a big industrial base, not tech, and all the STEM talent just becomes mechanical engineers, not software engineers, and half those who do become SWEs end up at trading firms.
fengb 4y ago
Mostly anecdotal opinion as a Chicagoan — Our tech scene has been largely driven by fintech and a few unicorns. And our unicorns tend to be much more bust than boom — Groupon being the highest profile one. Not sure if it's correlation or causation, but VC investment tends to be more conservative, and the ones I do hear about are mostly fintech. On top of which, Chicago wasn't all that tech friendly. Pay has been rather stagnant, and promotions above senior engineer didn't exist before Covid/remote stretched everything out. The exception to comp has been prop trading firms, which make oodles of money but... trader culture dominates over eng.
- cs137 4y ago
  I lived in Chicago and, when I was there, there were a lot of good people but the overall technical culture was mediocre--probably not worse than anywhere else, but not befitting what was once (and could be) among the greatest cities in the world. The presumption, except in high-frequency trading, is that the talented people go to the coasts (which is bullshit, because I've spent a lot of time on the coasts, and it's all socioeconomic) and so a certain fratty culture dominates. If WFH is permanent, it could be one of the best things for Chicago in a long time. It really is a great place to live--if you can find a good company. I also didn't find the weather to be that bad. April-November is a slightly cooler (nicer, in summer) version of the same thing we have on the east coast, and the winter tends to be mostly fine with only an occasional -20 cold blast. In my view, Chicago's biggest negative is its 1-2 hour drive radius. The city's beautiful. Northern Illinois, not as much. Starved Rock is nice, and the Indiana Dunes are alright, but most of the cool stuff in the Midwest is 3-5+ hours away. The flat landscape also suffers due to billboards and powerlines; the topography makes the city itself so much more more compelling, but it means the outlying areas get really ugly--because if there's any garbage within a mile radius, you're going to see it. On the other hand, it has one of the cheapest and most connected airports in the world, so that might make up for it.
UkrainianJew 4y ago
>Common diagnoses (crime, taxes, regulation) all undoubtedly make an impact - but none are as bad as SF/NY. SF/NY's tech scene gained momentum up before the surge in crime and corruption and is currently mostly coasting on inertia, driven mostly by ambition to tap into that abundant capital from previous cycles. The new frontier is currently in China.
- doublescoop 4y ago
  Aside from theft from motor vehicles, other forms of crime have been on the decline in SF over the last decade. (1) There is no surge in crime. (1) http://www.cjcj.org/news/12756 http://www.cjcj.org/news/12756
bedhead 4y ago
Former Chicagoan here. Grew up in Evanston and lived in Lakeview area for almost 20 years. We moved to a small town in Colorado a few years ago. Chicago is just constantly running against the wind. Violent crime is a game-changer (property crime is one thing, violent crime another), public schools are dysfunctional, taxes are bad and only getting worse, weather is terrible the majority of the year, and there's nothing particularly interesting to visit within a few hundred miles (though I've always loved western Michigan). Chicago has a culture that's gotten progressively uglier and makes a lot of people generally not want to live there. I could go on, and I'm not saying anything unique. It's just running against the wind and prevents Chicago from ever really taking off and reaching escape velocity. It would take a real unicorn to jumpstart things more. Btw you ask any former Chicagoan and they'll say the same thing: their only regret was not moving sooner.
- turndown 4y ago
  I've also lived in Chicago/Chicagoland >20 years. Obviously there are crime issues in certain parts of the city but most of the people I hear loudly complain about it are old white people that don't live here anymore. I have no idea what you mean by uglier culture. Also, for anyone not from around here, Chicago has a significant crime delta between neighborhoods that, if one were to read about it, can only be thought of in terms of extreme racial injustice. 0: https://upload.wikimedia.org/wikipedia/commons/7/7c/2013_Chicago_Homicide_Map.png https://upload.wikimedia.org/wikipedia/commons/7/7c/2013_Chi...
  - helloworld11 4y ago
    >Obviously there are crime issues in certain parts of the city but most of the people I hear loudly complain about it are old white people that don't live here anymore. So you've spoken to a large number of the hundreds of thousands of African Americans who live in the neighborhoods most plagued by crime and know that they don't complain about it? It just has to be some derogatory classification of subgroup such as "old white people", As if the hundreds of murders per year were little more than something for them to whine about? >Chicago has a significant crime delta between neighborhoods that, if one were to read about it, can only be thought of in terms of extreme racial injustice. "Only" in terms of racial injustice? So those violent crime numbers by neighborhood are entirely the fault of the aforementioned white people? The people actually committing them in these neighborhoods have no agency or fault in what they do to their own neighborhoods? This logic just keeps getting more twisted in the absurdities it has to push to sustain itself. Doubtless there is racial injustice in a U.S. city with a famously corrupt police/civil administration like Chicago, but in recent decades Chicago has had multiple black mayors and a large percentage of its government and police are staffed by African Americans or people of color in general. Yet they somehow have had no say or co-responsibility for anything that has remained problematic?
tptacek 4y ago
June-September is a weird range. We're the best city in the world from April to early June, for sure. Then we're too humid to sustain human life until the end of August. Then we're the best city in the world again until early December. Then we're so cold we have to hibernate with our increasingly vegan bratwurst stashes until April again. I don't think startup-friendliness has all that much to do with city greatness, or vice versa. San Francisco is smaller than Columbus, Ohio, both by population and by square mileage. Columbus isn't even in the conversation! It's just a network effect thing: SFBA was the right place at the right time, got a critical mass, and it became a received truth that if you're thinking about funding a company, that company should in SFBA, so it can interact with and recruit from other successful companies. If you're not looking to get funded, being in Chicago can be a big advantage. It was for Matasano, the company I co-ran for a decade in the '00s. The cost of living is low, every major city has a reservoir of talent that's going to stick around for reasons other than career development (family connections, just loving the city, &c), and, maybe most importantly, a diversity of real businesses that aren't part of the tech ecosystem, which is a customer base you need to learn how to support either way.
- throwaway894345 4y ago
  > We're the best city in the world from April to early June, for sure. Lol if you hate the sun and love the mud, then yeah that time of year is fine. > Then we're too humid to sustain human life until the end of August. Then we're the best city in the world again until early December. Agreed, although I don't mind December if only because things still feel festive in the city, and we don't get properly cold until January anyway. I don't mind bundling up for ~30° days when the city is at its most charming. But when decorations come down after the new year, temperatures plummet, the city becomes collectively depressed, etc then it's a pretty miserable place to live (though surely there are worse places).
  - tptacek 4y ago
    Deep winter in Chicago is pretty miserable. I grew up with it and value the changing of the seasons (California has only two seasons: yellow season and wet grey season), but not wanting to gut out February here is a perfectly cromulent reason to avoid the place. If you don't have a pretty healthy social system with indoor stuff to do during the weekend, it can feel a little like living through 2020 did, but for a couple months every year. I'm happy to hang out with the whiskey list at Delilahs, seeing a concert or two, and snagging tables at Publican, Juno, and Duck Inn during those months, but if that's not your thing, I can see how this place would get bleak.
throwaway894345 4y ago
> Chicago is the best city in the world from June-Sep I'm a Chicagoan who works for a successful Chicago startup, and I'm planning to leave this year precisely because I strongly disagree with "Chicago is the best city" (at any time of year). There are things that I appreciate about the city (which can be gained from occasional visits rather than residence), but here are some of the things that are driving me out (I'm not sure the extent to which these things have a bearing on its success as a tech hub): 1. There's virtually no nature within a 2 hour drive (you can hardly get past the suburbs in 2 hours after work). There are a few decent state parks (e.g., Starved Rock) that one could do in a day or two, but it's not like Seattle, Denver, or Phoenix where you can be in the mountains in ~40 minutes during rush hour. It seems like Chicago is a great city if you're big into sportsball and clubbing, but for those who want more from life, it leaves a lot to be desired. 2. Chicago has a few charming neighborhoods and the architecture downtown is beautiful, but in general most of the city is kind of ugly (lots of trash blowing around the streets). I particularly hate all of the vomit-yellow brick buildings that plague the north/north-west sides of the city. The more charming neighborhoods are also pretty unaffordable for most Chicagoans. 3. Even with respect to the weather, Chicago is hot and humid from June through August, which makes it pretty unpleasant to be outdoors for most of the day unless you're on the lake (which is invariably crowded). And of course from January through May, Chicago is either cold and bleak or muddy and bleak. If Chicago has a peak time, I would argue that it's September through December. 4. Chicago is deeply politically dysfunctional with respect to fiscal policy, policing, prosecution, etc (and things at the state level aren't much better). I'm happy to pay more in tax to a government that uses that money effectively, but Chicago's taxes are steep and it doesn't seem like that revenue is efficiently used. It's also extremely segregated--when people talk about "Chicago", they're almost always talking about the north side specifically. South and west sides may as well be in different states (if not countries) to most of us north-siders except for the overflow of crime (which admittedly isn't as bad as the news makes it out to be--we're not the worst city in the US for violent crime, we're "merely" the tenth worst of the largest 100 cities). 6. The city lacks any prominent sense of community. Most people don't know their neighbors (although I'm sure there's the odd building or block for which this isn't true). It seems like the overwhelming majority of people are transient and isolated ("alone in a crowded city"). A lot of people seem depressed as a result. 7. Chicago's COL is only low by coastal standards. It's still quite high compared with most of the country. Of course, the present inflation crisis and likely recession are probably going to make these comparisons a bit messier until things reach a steady state.
ruh-roh 4y ago
Is it really not thriving? Surely it's relative vs SF/NYC, but when I got here in the 90s, it was all just banking & insurance. Also advertising, but very little tech there. It was super frustrating at the time, but the last decade has shown quite a bit of growth of "modern" startups, imo. It may not be those other hubs, but as Mr Bourdain would probably say, Chicago doesn't care. On the weather... "A nice day in Chicago is a nicer day than anywhere else in the world." -- Anonymous. 75 degrees with no humidity is heaven here, and _everyone_ you see feels the same way. Outdoor dining, festivals, parks, etc. People grind through January just to see June, and it shows. 75 degrees with no humidity in San Diego is just another Tuesday.

xhkkffbf 4y ago

It is a great city, but the tax rates are outrageous and they're going to get worse. Just look at the funding of the pension plans. Illinois and Chicago have some of the worst funding ratios. They've promised too much to workers and never set enough aside. There's a reason why companies like Boeing or Citadel are fleeing.

colinmhayes 4y ago
Boeing left because their tax break ended for what it's worth.
- tptacek 4y ago
  Boeing was barely here to begin with. They consistently missed their job targets, despite being allowed to count contractors towards the anemic targets they were meant to hit. Citadel is a body blow, but Boeing? Who cares.
- Kon-Peki 4y ago
  A few years ago the Citadel CEO went through a very public and extremely acrimonious divorce, during which the wife and kids left Chicago for the east coast and refused to come back. So now, he's all alone, and seemingly getting angrier by the day. His politics are increasingly distanced from what people in the area are interested in, etc. Moving to a location where he might see his kids more often might just make him a lot happier and less angry. If so, that's good for him.
closeparen 4y ago
In what way is Chicago’s tax situation worse than SF or NY?
- eschulz 4y ago
  Illinois is generally in the bottom three of states for pensions being underfunded, and Chicago is normally the city with the highest or second highest sales tax in the US. As an Illinois resident I'm concerned about the high percentage of taxes over the next several decades that will go to service debt, and therefore not provide other services. I think this causes issues which scare away established employers as well as entrepreneurs (high crime rates, struggling public schools, etc). This will then drive away young people who are looking for good jobs, and therefore Illinois misses out on the taxes those people would pay over their careers and thus the situation spirals down further. https://taxfoundation.org/state-pension-funding/ https://taxfoundation.org/state-pension-funding/ https://www.taxjar.com/blog/cities-and-states-have-the-highest-sales-tax-rates https://www.taxjar.com/blog/cities-and-states-have-the-highe...
curiousllama 4y ago
This is a fair point. Long term tax issues could def be a factor. Even beyond the abstract potential bankruptcy: who wants to buy a house when 90-110% of appreciation will be eaten by the inevitable tax increases?
tptacek 4y ago
The tax situation is not great, but for tech workers, it ultimately just means that Chicago is not as advantaged over NYC and SFBA as it could be; the cost of living here is so much lower that it's hard for me to think of a scenario where you wouldn't come out substantially ahead. My kid brother is buying a starter home, in a relatively (obnoxiously) expensive part of Chicagoland, and to get the same house within an hour's drive of San Francisco he'd be looking at 4-5x the outlay. The property tax situation does mean that Chicago houses aren't mortal-lock speculative investments the way SFBA houses are, so there's that to contend with.

1123581321 4y ago

The venture money in Chicago is too conservative. It’s not a great city during the winter. There aren’t enough large, innovative employers in silicon hardware, or software. The state has latent brain drain due to taxes and a few other things. Source: have spent years trying to make it better. Edit: want to be clear that the money isn’t conservative in a good way, encouraging small, sustainable businesses. It’s reluctant to support those at a reasonable price as well.

curiousllama 4y ago
This is a new interesting point to me, which makes total sense. All the big $ in Chicago seem to go to prop trading, not VC. Combine that with a big industrial base, not tech, and all the STEM talent just becomes mechanical engineers, not software engineers, and half those who do become SWEs end up at trading firms.

fengb 4y ago

Mostly anecdotal opinion as a Chicagoan — Our tech scene has been largely driven by fintech and a few unicorns. And our unicorns tend to be much more bust than boom — Groupon being the highest profile one. Not sure if it's correlation or causation, but VC investment tends to be more conservative, and the ones I do hear about are mostly fintech. On top of which, Chicago wasn't all that tech friendly. Pay has been rather stagnant, and promotions above senior engineer didn't exist before Covid/remote stretched everything out. The exception to comp has been prop trading firms, which make oodles of money but... trader culture dominates over eng.

cs137 4y ago
I lived in Chicago and, when I was there, there were a lot of good people but the overall technical culture was mediocre--probably not worse than anywhere else, but not befitting what was once (and could be) among the greatest cities in the world. The presumption, except in high-frequency trading, is that the talented people go to the coasts (which is bullshit, because I've spent a lot of time on the coasts, and it's all socioeconomic) and so a certain fratty culture dominates. If WFH is permanent, it could be one of the best things for Chicago in a long time. It really is a great place to live--if you can find a good company. I also didn't find the weather to be that bad. April-November is a slightly cooler (nicer, in summer) version of the same thing we have on the east coast, and the winter tends to be mostly fine with only an occasional -20 cold blast. In my view, Chicago's biggest negative is its 1-2 hour drive radius. The city's beautiful. Northern Illinois, not as much. Starved Rock is nice, and the Indiana Dunes are alright, but most of the cool stuff in the Midwest is 3-5+ hours away. The flat landscape also suffers due to billboards and powerlines; the topography makes the city itself so much more more compelling, but it means the outlying areas get really ugly--because if there's any garbage within a mile radius, you're going to see it. On the other hand, it has one of the cheapest and most connected airports in the world, so that might make up for it.

UkrainianJew 4y ago

>Common diagnoses (crime, taxes, regulation) all undoubtedly make an impact - but none are as bad as SF/NY. SF/NY's tech scene gained momentum up before the surge in crime and corruption and is currently mostly coasting on inertia, driven mostly by ambition to tap into that abundant capital from previous cycles. The new frontier is currently in China.

doublescoop 4y ago
Aside from theft from motor vehicles, other forms of crime have been on the decline in SF over the last decade. (1) There is no surge in crime. (1) http://www.cjcj.org/news/12756 http://www.cjcj.org/news/12756

bedhead 4y ago

Former Chicagoan here. Grew up in Evanston and lived in Lakeview area for almost 20 years. We moved to a small town in Colorado a few years ago. Chicago is just constantly running against the wind. Violent crime is a game-changer (property crime is one thing, violent crime another), public schools are dysfunctional, taxes are bad and only getting worse, weather is terrible the majority of the year, and there's nothing particularly interesting to visit within a few hundred miles (though I've always loved western Michigan). Chicago has a culture that's gotten progressively uglier and makes a lot of people generally not want to live there. I could go on, and I'm not saying anything unique. It's just running against the wind and prevents Chicago from ever really taking off and reaching escape velocity. It would take a real unicorn to jumpstart things more. Btw you ask any former Chicagoan and they'll say the same thing: their only regret was not moving sooner.

turndown 4y ago
I've also lived in Chicago/Chicagoland >20 years. Obviously there are crime issues in certain parts of the city but most of the people I hear loudly complain about it are old white people that don't live here anymore. I have no idea what you mean by uglier culture. Also, for anyone not from around here, Chicago has a significant crime delta between neighborhoods that, if one were to read about it, can only be thought of in terms of extreme racial injustice. 0: https://upload.wikimedia.org/wikipedia/commons/7/7c/2013_Chicago_Homicide_Map.png https://upload.wikimedia.org/wikipedia/commons/7/7c/2013_Chi...
- helloworld11 4y ago
  >Obviously there are crime issues in certain parts of the city but most of the people I hear loudly complain about it are old white people that don't live here anymore. So you've spoken to a large number of the hundreds of thousands of African Americans who live in the neighborhoods most plagued by crime and know that they don't complain about it? It just has to be some derogatory classification of subgroup such as "old white people", As if the hundreds of murders per year were little more than something for them to whine about? >Chicago has a significant crime delta between neighborhoods that, if one were to read about it, can only be thought of in terms of extreme racial injustice. "Only" in terms of racial injustice? So those violent crime numbers by neighborhood are entirely the fault of the aforementioned white people? The people actually committing them in these neighborhoods have no agency or fault in what they do to their own neighborhoods? This logic just keeps getting more twisted in the absurdities it has to push to sustain itself. Doubtless there is racial injustice in a U.S. city with a famously corrupt police/civil administration like Chicago, but in recent decades Chicago has had multiple black mayors and a large percentage of its government and police are staffed by African Americans or people of color in general. Yet they somehow have had no say or co-responsibility for anything that has remained problematic?

tptacek 4y ago

June-September is a weird range. We're the best city in the world from April to early June, for sure. Then we're too humid to sustain human life until the end of August. Then we're the best city in the world again until early December. Then we're so cold we have to hibernate with our increasingly vegan bratwurst stashes until April again. I don't think startup-friendliness has all that much to do with city greatness, or vice versa. San Francisco is smaller than Columbus, Ohio, both by population and by square mileage. Columbus isn't even in the conversation! It's just a network effect thing: SFBA was the right place at the right time, got a critical mass, and it became a received truth that if you're thinking about funding a company, that company should in SFBA, so it can interact with and recruit from other successful companies. If you're not looking to get funded, being in Chicago can be a big advantage. It was for Matasano, the company I co-ran for a decade in the '00s. The cost of living is low, every major city has a reservoir of talent that's going to stick around for reasons other than career development (family connections, just loving the city, &c), and, maybe most importantly, a diversity of real businesses that aren't part of the tech ecosystem, which is a customer base you need to learn how to support either way.

throwaway894345 4y ago
> We're the best city in the world from April to early June, for sure. Lol if you hate the sun and love the mud, then yeah that time of year is fine. > Then we're too humid to sustain human life until the end of August. Then we're the best city in the world again until early December. Agreed, although I don't mind December if only because things still feel festive in the city, and we don't get properly cold until January anyway. I don't mind bundling up for ~30° days when the city is at its most charming. But when decorations come down after the new year, temperatures plummet, the city becomes collectively depressed, etc then it's a pretty miserable place to live (though surely there are worse places).
- tptacek 4y ago
  Deep winter in Chicago is pretty miserable. I grew up with it and value the changing of the seasons (California has only two seasons: yellow season and wet grey season), but not wanting to gut out February here is a perfectly cromulent reason to avoid the place. If you don't have a pretty healthy social system with indoor stuff to do during the weekend, it can feel a little like living through 2020 did, but for a couple months every year. I'm happy to hang out with the whiskey list at Delilahs, seeing a concert or two, and snagging tables at Publican, Juno, and Duck Inn during those months, but if that's not your thing, I can see how this place would get bleak.

throwaway894345 4y ago

> Chicago is the best city in the world from June-Sep I'm a Chicagoan who works for a successful Chicago startup, and I'm planning to leave this year precisely because I strongly disagree with "Chicago is the best city" (at any time of year). There are things that I appreciate about the city (which can be gained from occasional visits rather than residence), but here are some of the things that are driving me out (I'm not sure the extent to which these things have a bearing on its success as a tech hub): 1. There's virtually no nature within a 2 hour drive (you can hardly get past the suburbs in 2 hours after work). There are a few decent state parks (e.g., Starved Rock) that one could do in a day or two, but it's not like Seattle, Denver, or Phoenix where you can be in the mountains in ~40 minutes during rush hour. It seems like Chicago is a great city if you're big into sportsball and clubbing, but for those who want more from life, it leaves a lot to be desired. 2. Chicago has a few charming neighborhoods and the architecture downtown is beautiful, but in general most of the city is kind of ugly (lots of trash blowing around the streets). I particularly hate all of the vomit-yellow brick buildings that plague the north/north-west sides of the city. The more charming neighborhoods are also pretty unaffordable for most Chicagoans. 3. Even with respect to the weather, Chicago is hot and humid from June through August, which makes it pretty unpleasant to be outdoors for most of the day unless you're on the lake (which is invariably crowded). And of course from January through May, Chicago is either cold and bleak or muddy and bleak. If Chicago has a peak time, I would argue that it's September through December. 4. Chicago is deeply politically dysfunctional with respect to fiscal policy, policing, prosecution, etc (and things at the state level aren't much better). I'm happy to pay more in tax to a government that uses that money effectively, but Chicago's taxes are steep and it doesn't seem like that revenue is efficiently used. It's also extremely segregated--when people talk about "Chicago", they're almost always talking about the north side specifically. South and west sides may as well be in different states (if not countries) to most of us north-siders except for the overflow of crime (which admittedly isn't as bad as the news makes it out to be--we're not the worst city in the US for violent crime, we're "merely" the tenth worst of the largest 100 cities). 6. The city lacks any prominent sense of community. Most people don't know their neighbors (although I'm sure there's the odd building or block for which this isn't true). It seems like the overwhelming majority of people are transient and isolated ("alone in a crowded city"). A lot of people seem depressed as a result. 7. Chicago's COL is only low by coastal standards. It's still quite high compared with most of the country. Of course, the present inflation crisis and likely recession are probably going to make these comparisons a bit messier until things reach a steady state.

ruh-roh 4y ago

Is it really not thriving? Surely it's relative vs SF/NYC, but when I got here in the 90s, it was all just banking & insurance. Also advertising, but very little tech there. It was super frustrating at the time, but the last decade has shown quite a bit of growth of "modern" startups, imo. It may not be those other hubs, but as Mr Bourdain would probably say, Chicago doesn't care. On the weather... "A nice day in Chicago is a nicer day than anywhere else in the world." -- Anonymous. 75 degrees with no humidity is heaven here, and _everyone_ you see feels the same way. Outdoor dining, festivals, parks, etc. People grind through January just to see June, and it shows. 75 degrees with no humidity in San Diego is just another Tuesday.