However, for live in owners, in terms of happiness with their neighborhood, minimal out of pocket expenditure (total price), and cap rates (maximized rent per investment) I have found clients most satisfied with, in order, Humboldt Park (the eastern pockets), sections of Logan Square and Avondale, and the eastern sections of Albany Park. Additionally, Bridgeport is providing exceptional value on multi-units right now despite the lower rents.
Chicago is full of incredible neighborhoods that offer something different for everybody, and if you have more money to invest, there are other options that will get you cap rates not much different than the above.
Take the other posters' advice, and rent for a year. You'll realize what works for you. And realize if you're going to become one of those Brick Snobs, and accept all buildings as equals!
I'm a big fan of Multifamily buildings and consider them a very good investment to buy in today's market, as long as you have the right location.
Most of the areas in Chicago are now affordable, but there's a few neighborhoods I'd like to point out where I've seen that prices have stabilized and demand is on the rise.
Feel free to contact me and we can discuss the options available.
Jose Hernandez, sfr
Coldwell Banker Residential
676 N. Michigan Ave.
Most areas have gone down in value. You have to find a home that not only offers good potential appreciation but also meets your budgetary abilities.
Work with a Lender and Realtor to assist you.