House hacking in Chicago neighborhoods

Depends on what your buying criteria is - budget, ROI, neighborhood class, etc all need to be considered. The quality of each of those neighborhoods is block by block. Niche.com is a great tool for gauging the quality of a neighborhood and South Shore, Woodlawn, and Chicago Lawn are all considered C class. I've sold a few buildings in those areas and you can find decent opportunities.

South Shore in particular has very large 2-4 unit buildings from what I've seen. They often have units with well over 1000 square feet and oftentimes 3-4 beds/2 baths per unit which is great for getting stronger rents. I analyzed a few house hack deals there recently though and the numbers didn't look promising post move-out. But if you analyze enough deals you can probably find the right fit.