I won't argue about the structure of segregation in Chicago. But in terms of the travel, I live in Bridgeport, which is on the south side, and take the Red Line downtown. I have never once heard a bad word from anyone on the crowded train, and I am often the only painfully white person in the car. I have no hesitation about walking around the neighborhood, or anywhere downtown.
My experience is vastly different from yours. I have lived in the Chicago area for many decades, and two years here in Bridgeport (not far from Sox Park).
I think in predominantly white neighborhoods like Bridgeport, you'll see fewer issues especially with its large police presence on duty and off duty.
I take it you've never been a victim of a "wilding" in River North like I've had. Nothing like getting targeted and getting swarmed while eating at an outdoor patio at State and Ontario or later that exact same night waiting at the Grand red line stop.
My experience is vastly different from yours. I have lived in the Chicago area for many decades, and two years here in Bridgeport (not far from Sox Park).