Directions are easier with grids. Numbering systems that ascend and descend from a particular central point make sense. State and Madison is zero. Anything else

Directions are easier with grids. Numbering systems that ascend and descend from a particular central point make sense. State and Madison is zero. Anything else is a higher or lower number in the direction you are relative to that intersection. 100 numbers is one block. All streets have numbers, even if they also have names. Most of the South side also uses numbers for names of east-west streets... so 30th street is 30 blocks south of Madison, and addresses will be 3000 S. North-south streets you can memorize, and would likely get by with only knowing a half dozen main ones. North side has a bunch of main through streets that you can orient around. You can get a rough sense of how far north or west you are. Or you can fall back to the numbers. 5000 north is 50 blocks north, which is pretty far north. If you don't have google maps you can usually go in two straight lines to just about anywhere. Just keep going until you are at the right east-west spot, and then do the same until you are at the right north-south spot. And use the handful of diagonal streets to be fancy.