Jobs are pretty slim in Chicago and rentals are at an all time high due to the poor housing market, so people are renting not selling.
The funny thing about Chicago is you can live in a nice area, walk two blocks and it’s awful. Also Chicago neighborhoods can change quickly, like in two years, it can go from good to bad or vice versa.
The best way to get a flat in Chicago is simply to find an area you like and then walk around, Chicago is well known for a city that doesn’t advertise its apartments. I can’t tell you the number of people who say, “Mark I wish I had taken your advice and walked around, 'cause now I’m overpaying.”
If you’d like a “house and small yard” you’re going to be pretty much on the NW side or the south side, which is mostly African America, but it does have nice areas too. Inner suburbs like Oak Park and Evanston tend to be overpriced, but the southern “inner suburbs” like Evergreen Park and Oak Lawn are nice with much more affordable housing.
It depends on what you have. Parking is outrageous in Chicago, so if you must have a car, you have to find a flat with that or you’ll be paying not only your monthly rent but an equivilent cost to park the car, or in parking tickets.
Chicago has a lot of nice neighborhood parks where kids can play. So you may need a yard.
In April when the whether gets nice, definately plan on a weekend trip to Chicago. Go online to the “Chicago Reader” and Craigslist and get an idea of what flats go for online.