I noticed the Chicago market has changed quite a lot since I started back in 2018. I have seen interest rates change from four to two to seven percent from 2018 to 2023. One thing that did really well during this time is multi-family properties. However, finding these properties at the right price is close to impossible. They are there, but they get snagged quickly. The multi-family properties I have been able to snag are due to some decent amount of work needed (negligent owners), not TLC. Even with an FHA, the work needed can creep upwards of similar or more than the closing costs, so you're looking at doubling your cost to own a multi-family property.
Any good news? Well, the rents in Chicago have been raising, even in the Southside, which is mainly coming from one particular neighborhood: Pilsen. The closer a property is to Pilsen the more you see the rent and value appreciation take affect. For example, I have bought a property in an undesirable area, and noticed that the rent and value hasn't changed much. While one which is very close to Pilsen increased by 50% in both rent and value. In any case, understanding the neighborhood is important to investing in Chicago. Drive around, ask people that live there how they feel about the area, and, if you can, live there for a year. I have done that with all of my properties (except one - I am sure you can guess which one), and it has helped me gauge the market.
Cheers!