My favorite way to see a place is usually to just wander in, get lost, and see what you run into. Having all the information in the world at easy access makes it easy to forget that having no plans and discovering somewhere on your own is a totally legit option.
On our second day of exploring Chicago, we opted to check out everything outside of its central downtown area. We spent a fair part of it on the South Side, around Hyde Park enjoying a walk alongside the snow.
This area was also full of Secret Service. It so happened to be Obama’s old neighborhood and they still own the house on the block. Every restaurant nearby throws out the ‘Obama ate here’ claim. He and Guy Fieri have to be the most frequently braggged about customers.