It would not be fair to have a discussion about investing in Chicago single family homes without covering the negatives also.
Every investment has some drawbacks, no investment is perfect .
There are more headaches involved with real estate than with simply putting your money in a money market account or mutual funds. Chicago single family homes are more difficult in some respects because they are spread out. This makes it harder for showings and repairs versus an apartment where all the units are in one location. There is also more paperwork, because each house has its own mortgage, property taxes, insurance, etc. Management takes some time, but if you develop a system and stay on top of it, it is not all that hard.