Chicago, Illinois

People who aren’t from Chicago tend to think of it as a big slab of a city - without the distinct boroughs of New York, or the famous neighborhoods of Los Angeles. But if you live in Chicago your neighborhood defines you in ways the whole city does not. 77 different neighborhoods, each worthy of celebration on its own: each filled with a unique vibe, culture, and history that longtime residents come to embrace.

What’s also cool though is that the other 76 neighborhoods are unique adventures for you to experience. You can live in the electric energy of downtown and in minutes scoot out to the warmth of a Cubs game in Wrigleyville, or the epicenter of cool on the West Side (sorry Wicker Park). 77 different neighborhoods, one that is your own, and 76 others all at your disposal.

Let's switch to what's tough about Chicago. Winters may not kill you but damn, they’re gonna hurt. Everyone knows about the cold, the wind, and of course, the snow, but the thing they don’t warn you about is how grey the skies remain for so long in winter. The Great Lakes cast a low, heavy layer of clouds over the city, creating a perfect storm of cold, wind, snow, and clouds throughout January and February. If you can survive that stretch though you’re home free.

Architecture and building types matter a ton in cities that get as chilly in the winter (and hot in the summer) as Chicago. Lifestyle here is driven more by your home or building than other cities so let's dive into that first. Chicago has every kind of place you can live -- high-rises downtown, bungalows, two-story flats, big brick single-family homes, and all the rest. Most unique to Chicago though is The Courtyard apartment building. These are distinct 3-story U-shaped buildings with grass courtyards, mostly built between the 1910s and 1930s when fire hazards and regulations prevented builders from going taller. There are so many other ways to live but everyone should get a chance to live in one of these sometime.

Beyond the architecture, you'll find beautiful beaches, and a silly number of music festivals, including Lollapalooza, Pitchfork Music Festival, and the Chicago Blues and Chicago Jazz Festivals. Chicago is excellent at bringing people together when the weather gets warm.

The city has a great food scene, seriously, watch The Bear. It has excellent transit, so not having to own a car makes it even more affordable. Many say it has most of the perks of NYC but at a fraction of the cost and a more favorable salary-to-cost-of-living ratio. That makes it attractive to couples and young families, aspiring to buy a condo or home and take advantage of the excellent public school systems in the suburbs.

Finally, Chicago has a much more relaxed vibe, people aren’t rushing or trying to get ahead quite as much. There is an ambitious and hard-working culture but the city moves at a less stressful pace than NYC or San Francisco.

Check out the calendar of events to see how jumping this city gets.

In terms of how schools are assigned, children are guaranteed a place in the neighborhood school to which your home is assigned as long as you fill out the forms to enroll them in a timely manner. If you don't fill out the forms in a timely manner and the classes fill up, your child may be assigned to another adjacent neighborhood school for a year until they can get staffing figured out for the school your child would have been assigned to. The assigning of homes to schools is done usually by distance but in the past had some political reasons to not always be. Under a new state law, all school catchments will need to be regularly re-assessed with the default assumption being that the nearest school should be the appropriate neighborhood school. This will not change the school assignments for currently enrolled students though unless parents opt into the new school they would normally be assigned to. Also, at any time if you are unhappy with your neighborhood school, you can apply to send your child to any other neighborhood school in the city. I'm unsure how that approval process works.

Beyond the neighborhood schools, you have the magnet schools which are admittance by application only. Some are special interest schools with a focus on STEM or the arts for example. Others are purely academic in how you get into them. In terms of the application process, they all require some form of test and sometimes ask for recommendations from teachers. They are not looking not only for top scores on the tests but for relative scoring position when compared against other similar students (that is to say, against your child's peers so being top 10% in the district doesn't help if they're only top 30% in their school). They do this as measurable intelligence and aptitude on tests is primarily driven by home life and school environment moreso than the student's natural aptitude. So the hope is that by using relative ranking within schools that they create an equitable process that manages to bring the students with the greatest natural or learned talent to the magnet schools without disadvantaging poorer communities in the city while still giving some advantages to wealthier households who can better prepare their children for the entrance exam.

What this ends up doing is that in the wealthiest parts of the city, up to 20% of students from their elementary schools get sucked up into the magnet schools while in the poorer areas, it is around the top 8-15% (roughly). This is often why if you look at standardized test scores for places like Lincoln Park High School or Lake View High School it looks like the school is bad but in reality the top 20% of students from the elementary schools feeding it were all admitted to the top magnet schools.

Basically, if you want "good" schools live in a school catchment with high income families as that's the best indicator of a student's success with the second being the number of books their parents had in the household (not owned, in the household so the library is fine) on average while they were a young child. But that said, even the lower income areas can be great. For example, my wife taught for an amazing 1+ rated elementary school in a middle-income Hispanic community where the parents were focused on their kids having an easier life than they did. That school sent around 16% of its students to the top magnet high schools.

Yes, CPS has a bad reputation because of fear mongering and people not talking about individual schools within the system separately. But overall, CPS makes up 5% of the top 100 high schools in the USA based on matriculation rates to top rated universities. If you expand to the top 250, CPS still is about 5% of the schools in the list. Please keep in mind that the City of Chicago is a bit less than 1% of the US population. So this indicates that CPS greatly outperforms expectations as an overall school district.