Share 'Visiting Chicago, would love advice, rent or bring, saftey, bike culture, ridability...food'

Hello Gang! I am visiting Chicago the last week of September into the first week of October for the first time. I am staying at what I believe is a central hotel, The Blake. I am traveling with my wife who has health issues that require her to walk with a cane, can't be on her feet the way i can, meaning i am going to have some free time on my own. I was thinking about bringing my bike so that wh…