Grew up in the northwestern burbs that butt up against the city. It was great and we'd ride our bikes to Fullerton Ave beach every now and then. It was an all day outing and our parents would've killed us had they known. But that was when a kid went out and played and you just had to be home by dinner. I don't miss Illinois per se, but I do miss my family and the fun parts of Chicago so I go back about every six weeks or so.
If you haven't seen her street photography yet, check out photos by Vivian Meier. There is an interesting movie about her as well. She captured the downtrodden parts of the Chicago in the 60s and 70s as well as the north shore beaches. She was a nanny for some folks along the north shore but took the kids into the city for outings....like Maxwell Street! She developed her film but never showed the results. She lived in New York for a while as well. She had a storage locker full of undeveloped film and someone bought the contents after she stopped paying on it after she died. He developed the rolls and found a treasure trove! Movie is FInding Vivian Meier and its worth the time.
www.vivianmaier.com/