Low quality of life. City & state broken.
I was unfortunate enough to live in Chicago for several years. First of all the weather is horrible. People know the winter is bad but the summer is the worst season, disgusting humidity combined with many 90+ degree days.
Chicago is known for it's violent crime which is true but there are parts of the city that have very little crime. I'm not sure where I heard this & can't take credit but here is a great summery of Chicago: It's like Detroit and San Francisco had a baby. Similar to Detroit with horrible climate all the rust belt problems like violent crime, outdated infrastructure, old pollution/remnants of heavy industry, corrupt government. It's like San Francisco in that there are some great urban neighborhoods with access to transit, parks, culture, grocery stores but only people in the wealthiest 5% can afford to live in these neighborhoods. Chicago has a relatively diverse economy even more diverse than strictly tech based SF or auto based Detroit.
It's odd, in neighborhoods like Lincoln Park, Wicker Park, Bucktown that have access to mass transit and where you can live an urban lifestyle the people that live there live a suburban lifestyle with two cars(usually oversized SUV's).
The city has some nice parks mostly along the lakefront but if you live in the western parts of the city the lakefront is not easy to access for daily or regular use despite being only a few miles as the crow flies. If you like access to nature & outdoor sports there is none here. You can go on a nature walk in one of the forest preserves in the burbs but nothing close to an actual hike. In fairness Chicago is not known for outdoor sports or nature.
The police department is just a taxpayer funded organized crime syndicate. You will be disproportionately impacted by this if you are black or hispanic. The city has paid out hundreds of millions of dollars for settlements for their inept police force. This is the same police force that used to have a torture site from 1972 to 1991 to force confessions from people to say they "solved a crime". This is absolute fact: see John Burge. The police are not much better now.
The city has a lot of food options from low cost to ridiculous expensive. In fact eating is like a form of recreation in Chicago & it is reflected in a significant portion of the population is obese.
Architecture is something people in Chicago brag about but really if you have seen one glass skyscraper you have seen them all.
Another negative is that Chicago is located in the state of Illinois which is also corrupt and broken, probably broken beyond repair. This is a reflection of the population, you will here "It's just the way it is." over & over. They accept this backward political system and do nothing to change it.
The traffic is horrible & there are super aggressive angry drivers. The mass transit is ok if you live near metra or cta trains. Mass transit is just a problem everywhere in the US. Our automobile centric transportation is a complete waste of time & money.
I have been fortunate to live in many places and I can say with great confidence Chicago has the lowest quality of life and at a high cost. I would certainly never recommend moving here and I don't even think it's worth visiting.
Eric | Denver, CO