Check the weather the day before you come in to see. Usually tennis shoes would be fine, but if it's recently snowed, boots might be better in case of snow and ice

Metered parking isn't too hard to find in neighborhoods in the North or Far North Side.

Where have you gone in Chicago in the last year or two outside the loop that it was difficult to find a meter? That's the side effect of our bad meter deal, rates are high enough that people won't pay them.