It actually is very difficult in Chicago. There is a lot of politics at play.
I mentioned before that my church is the largest property owner in Washington Park. We own probably up to 50+ properties from Garfield to 63rd st. I'm talking about large apartment complexes. That tall apartment tower on 63rd Michigan is even owned by us. We have built a lot of new construction as well. We have a separate redevelopment corporation that manages all the properties. Our priest is the CEO of the organization and he is one of the most powerful and connected black men in the city. Because we own so many properties, naturally, we would want businesses in the area for our residents. But even with our priest's connections (he's like a Father Pfleger but with more connections and money) it's still very difficult to get businesses in the area.
At best, with partnerships with the University of Chicago, we've been able to attract a few businesses along Garfield Blvd in Washington Park. But most of Washington Park is zoned for residential use. There's not many places where you can setup businesses within the actual neighborhood because of the fact.
But like I said, it's very difficult, even with all the connections and money. I'm not even sure what the process is when our priest, whose on the board of the Obama library and the University of Chicago Hospital as well as other prestigious institutions around the city, can't even get the type of businesses we need in the neighborhood.
Its not difficult if you're already zoned for it.. Im sure its a issue of you have to build from the ground up. Plenty of wards on the southside have ready to go buildings that would be zoned for grocery stores. Washington Heights just isn't one of them.