I live in the Chicago area and have brought up 5 DCs here, and I love it.
I actually live in a suburb that abuts the city limits. It has been a really wonderful place to bring up children. It is walkable and bikeable (there are Divvy bike rental spots all over the place), there are lovely public facilities (parks and rec department that maintain great playgrounds and parks, including tennis courts, basketball courts, skate park, and run classes in all sorts of areas from sports to arts for all ages) libraries to die for, two public swimming pools, an all year rink, playing fields and volunteers who coach t-ball, baseball, softball, soccer, volunteer organisations that run children's sports leagues. The schools are great in those places. Access to Chicago is fast and convenient by rail or car.
A previous poster mentioned Evanston - there are other places of similar ilk: Riverside, Oak Park, River Forest to name some obvious choices. Skokie is also very nice. All are very middle class, with Oak Park, Evanston and Skokie also very diverse in terms of income levels, and ethnic and racial integration. Oak Park, Evanston, Skokie and River Forest also have both local and regional rail links to Chicago itself, Oak Park with two local rail lines going all the way through is especially blessed. Riverside has a regional rail link. Oak Park, Skokie and Evanston have borders with Chicago.
Within Chicago itself there are many areas that are single family home-style residential, that are nice, and have solid local schools. Beverley/Morgan Park spring to mind immediately, on the SW side. Hyde Park is a gorgeous area with lots of apartments and also single family homes, a very lively arts scene, restaurants, and the lake at your doorstep. Lakeview is nice (apartments for the most part). Edgewater, Near South Side/South Loop/Printers' Row (proximity to Shedd Aquarium and Adler Planetarium), Lincoln Square and North Center are also nice, and maybe Portage Park. Roscoe Village is nice, as are Ukrainian Village, Sauganash, Edison Park, Bucktown, Mount Greenwood, Rogers Park...
You do get cold winters in Chicago, but obviously millions of people survive and thrive. Kids walk to school - for the most part there are no uniforms except for private schools (in the burbs anyway) so dressing for the weather is possible. Winter sports are very popular. The streets are cleared in both city and suburbs, fairly fast, and people do not for the most part miss school or work because of winter weather. People shovel the sidewalks in front of their houses and will often do their neighbours' sidewalks too. My experience of winter is obv different from that of 24balloons. Dress appropriately and nothing will stop you ime. For me, appropriately means a down filled 3/4 length jacket, jeans and a pair of snow boots for snow, and other boots for cold. It is a dry cold. My DCs walk to school with jackets, jeans, hats.
Summers can be hot and humid. The lake moderates temps right along the shore (including the eastern half of the city) to a certain extent, but by mid July it is definitely hot everywhere. AC is a necessity - most apartments and houses will at least have window units. Evanston is on the lake and has public beaches and communities elsewhere have public pools. There is lots to do indoors all over Chicagoland.
You can also get away to Wisconsin or Michigan or Indiana very easily for lovely holiday spots - Door County and Washington Island in Wisconsin are very affordable and easy to get to, Wisconsin Dells is pretty, the Indiana Dunes can be accessed by train from the city, Michigan offers a multitude of lovely sandy beaches and other attractions for family getaways. Summer fests of various stripes can be lively events in Chicago and Milwaukee. Chicago offers endless night life, restaurants, a cultural scene that features everything from the Chicago Symphony Orchestra and the best classical music station in the world to a very active avant garde rap and rock scene, and of course Chicago blues. There are incredible opportunities for children and adults to get involved in music and the arts. The Art Institute is a fantastic resource, as is the Old Town School of Folk Music.
It is easy to be misled into thinking that the gun violence that makes the headlines affects the whole city and suburban areas. I leave my door unlocked more often than not, and rarely lock my car. My mum (in Dublin) is horrified at my casual ways. Most areas of the city are unscathed, and most of the suburbs too - there is not even graffiti where I live. If it appears anywhere it is cleaned off by the police.
In terms of attitudes, Chicago is a Democrat-voting area. It grew as a blue collar, RC and Jewish town, very Irish, German, Italian and Polish in terms of ethnic mix of the majority of settlers, with protestant fundamentalism not much in evidence at all. A birds' eye view of the city and near suburbs will reveal many of the old RC churches built by the communities they served. It currently has a huge hispanic population and of course the Great Migration meant a huge influx of African Americans from the Delta (hence the Blues). The Great Migration brought the black Baptist church to the city. The suburb where I live is known for being very progressive.
Some of the inner suburbs were founded by fairly uptight members of straightlaced churches (Evanston, founded by Methodists, was once jokingly known as Heavenston; Oak Park was described by native son Ernest Hemingway as a place of wide lawns and narrow minds) but the influence of the more relaxed European (Jewish and RC) immigrants changed all that. Oak Park and River Forest were for a while during the 60s and 70s known as Toke Park and Reefer Forest...
Chicago has several major universities - Loyola, Univ of Illinois at Chicago, DePaul, and the U of Chicago (