I loved staying in Jermaill's place because I had a boutique hotel experience at a fraction of the expense, truly luxourious bedroom, private bath, easy access to public transportation. I bought a 7 day unlimited trip Ventra card and wore it out, used the bus/subway mere blocks away to explore south, central (Loop) and north Chicago with ease. If you are not familiar with navigating bus/train services perhaps Uber in the evening. Google maps was not accurate many times and I mapped my own way via CTA and a paper map of system the night before or for a bit before I left for my excursions. Exploring Chicago from Jermaill's place was a breeze.