I have lived in Chicago area my entire life and have been investing in RE for last 5 years with about 80 doors...My advise is FOR GODS SAKE DONT GO TO CHICAGO it sucks in so many ways! Appreciation is not near as high as other areas (I bought a Bonita Springs Florida 2 bedroom home in December of 2020 and sold in April of 2021 and made $95k, I did no work simply appreciation), ( I also bought a lakefront Lake of Ozarks home that I airbnb and make about $1000 a month true profit and it has appreciated over $100k in less than 2 years)
The city of Chicago also has laws and restrictions and building code issues that frankly suck for home owners and investors, you will be in for a lot or red tape if you buy IN the city or the wrong suburb. A good contractor to do the work is EXTREMELY hard to come by in this area.
Finally PROPERTY taxes here are the second worst in the country and NOT getting any better. While you are fixing to flip a property you will pay a fortune in real estate taxes and not have quick appreciation...in somewhere like South Carolina you will pay about 1/3 the taxes while you fix the property and see double the appreciation as well during that same time frame
I invest mostly for cash flow and buy in the FAR west IL area in small towns...no crime, good tenants, far less city oversight in how I run my business and much easier to evict a tenant... in short NEVER BUY ANYTHING IN COOK COUNTY, it takes MONTHS to get a court date to evict a tenant. You can also go to www.heyjackass.com and see the DAILY shooting reports for Chicago, we are really shooting a ton, breaking records every week... although we tend to not kill many people because we are bad shots, we still shoot a ton of people... the city is almost considered a war zone
I am also moving to South Carolina this summer while my new home is being built... this state is bad enough that my family and I had to move! We have watched a ton of people leave mostly due to crime and taxes and a horrible political and union labor structure that cannot be fixed.
If you want to be in the Midwest look toward central IN (places like Carmel IN and surrounding areas) and also Iowa (areas like the quad cities can be good)...but, as another member mentioned, people are heading to the sunshine states...if I was FLIPPING then I would buy in those markets. The younger generations want turnkey on trend homes, most dont know that things can be fixed, so you can likely find beat up properties that the younger buyer wont even consider, fix them on trend with what they want in a home, and then sell them at a nice profit...in the HOT areas the properties that dont sell quick need work, if you can do that work you can make a great profit