I disagree with some of the above posters that living for free is not possible in Chicago anymore. Its definitely more difficult and probably impossible in the popular and rapidly gentrifying areas though.
I'd say your best balanced area to look in general is the SW side of the city. Prices are high but they are less pricey than the north side or the south lakefront neighborhoods. They are relatively stable and there's also potential for growth. Bridgeport has high prices. Down archer there's McKinley park which has growth potential due to proximity to the orange line EL Station. There's also some redevelopment in planning stages in the former CMD district on pershing road. Those reasons and the demographic changes already occurring there lead me to be bullish on that area. With proximity to Chinatown and Bridgeport, the demographics of the neighborhood are changing.
https://mckinleypark.news/news...
Southwest of there you have Brighton Park which is a working class neighborhood with a stable tenant pool. There has also been some demographic change there to a smaller extent with some Hispanics moving out and Chinese moving in. Further southwest there's Archer heights which has a similar purchase price to brighton park and a stable tenant pool of working class families. The amount of house hackable 2-4 unit multifamilies drops off as you go SW of midway Airport.
In these neighborhoods you have the most likelihood to live for free in a relatively safe neighborhood by househacking. I bought two househacks in McKinley Park in 2021 and 2022 and after small cosmetic improvements, I live for free in the second property and bring in about $700 monthly cash flow from the first.My purchases were before the interest rates rose. I have found great renters in the neighborhood with good incomes and credit scores above 750.