Boston is much easier to navigate and get direction, go until you hit the triangular intersection, take the left branch, you’ll eventually find a rotary has brushed up on your road, take that etc etc. Each intersection should endeavor to be a unique, memorable point!
But you're not going to give directions as "pass 15 intersections." If you want to get to, say, 55th and Cicero from the south, you'd say get off I-57 at 167th street, turn north onto Cicero, and, well, you can watch the streets count down. A savvy navigator would know that Chicago has 8 blocks to the mile (outside of downtown), so 55th is 14 miles north of 167th, but you don't need to know that: every major mile street will have a stoplight, and the stoplight will inform you which street it is.
Of course, 55th and Cicero is a bad example, since it's the intersection of two major streets (and the business there is a really, really obvious one that you can't possibly miss). If you're off of a minor street, you might instead say something like "it's the second left after Pulaski"--Pulaski is one of the big north-south mile streets, so one would have a rough idea of how far away that is, and you don't need to start counting until after crossing the main mile street.
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.