not really. I grew up in chicago, graduated college there, have my family in austin now and go back frequently. anything that makes chicago a better city is all downtown, and not very family friendly aside from a few museums. Almost everyone I know who has families there have moved out to the far suburbs and rarely take advantage of the things that makes it stand out. It does have huge parks, a beach, world class museums, greats zoos, professional sports teams, a beautiful aquarium, but most of those are filled with long lines of tourists, expensive or can't be taken advantage of because of weather. A big portion of the beaches get shut down mid-summer because of ecoli, and frozen 6 months of the year. millenium park is probably the most family friendly addition in recent years and is great, but if you don't live downtown its not like you just skip over there in 15 minutes like you can in Austin. Want to Ice skate in front of the beautiful skyline, yeah thats gonna take about 4-5 hours and $60 after parking and fees, unless you want to bundle your kids up in winter coats and drag them on the brown line and walk about 2 miles in snow and ice.

The city is also surrounded by huge areas of industry and blight. The Chicago Public Schools are shit holes. Most well to do families have kids in very expensive daycares and private schools, or move out to the near suburbs like Oak Park, Evanston, Naperville, Lake Forest, Shaumburg - and those suburbs make Round Rock seem quaint.

And as far as affordable. Its not. It has very high taxes and several regional transit systems that bleed money and constantly raising prices. And most of the suburbs in cook county have high taxes as well, since the whole city is in the county and they share a lot of the resources.

However, the drinking water is some of the best on the planet, snow days during school are epic, the amount of ethnic diversity is amazing, and growing up walking every where or using public transportation is great for kids. Its helps realize life is more than just driving everywhere like they do here in texas.