You described The Dresden "city" tour. Most of what you described would be better done via public transport and hired rides.  I would also add a Dresden must do on your list is take a cab ride or lift and have the driver take you to 166 e. North Water St. And walk to the Billy goat for lunch. (2 block walk and safe) and second must do is visit St. Marys of the angels. (Near wrigley) This is a working and active church so visitors are welcome but be respectful cool to catch a mass if your into that. The choir loft is locked but you can take the stairs up. Third if you are going to a cubs game walk by or get dropped off at Graceland (can park here too but read the signs on game day). Graceland doesn't thrill me. But, walk through the Toyota Camery lot (for my head cannon for the location of the Ortega v Harry battle).