Thanks for the replies, everybody.
You memorize the main streets.
Despite the grid that my city generally follows, that is what you have to do here too, because the minor streets don't always continue all the way without being interrupted, especially when they meet the new car-centric neighborhoods on the edge of the city, where they are discontinued, and only the major (arterial) streets on the sides of the neighborhood are continued.
We have a numbering system, so if you're going to a new place that's not on a main street, you only need to learn the street it's on: the other coordinate is given by the street address.
Indeed, my city's street address includes that too.
Also also, we actually have a public transit system, which I generally prefer... city driving gets old.
Unfortunately, my city (like many American cities) has very poor public transit, so I'm basically forced to drive. The buses come to a stop only once per hour, so if you get off at a stop to shop and it takes you only 15 minutes to shop there, you're forced to wait for another 45 minutes for the next bus, which is very inconvenient and wasteful of time. Also, there are no trams, and certainly no subway.
* West of Pulaski, streets are alphabetized, for some reason going from L's to N's only.
Looking at the map, it looks like they go up to P. (But maybe that's technically not Chicago anymore?) Also, some streets, but not all, seem to be in alphabetical order, and there's some outright exceptions, like
Sayer Ave, but at least generally if you're looking for a street that starts with N, you know that you've overshot it if you hit the O's.
i have to say i'm surprised at your surprise that streets hace names instead of numbers!! i don't know that i've ever been to a city where moat streets were numbered, that's a new one for me
If it makes you feel any better, the new car-centric neighborhoods of the city are doing their best to undo this, by filling their unwalkable neighborhoods with streets that break the grid, are shaped as loops, courts, and dead-ends, and have name names instead of number names.
different cities will follow different patterns. the fact that the pattern in one city is different from the pattern in another doesn't mean either is "illogical". part of learning to navigate is learning which patterns are local and which patterns are more broadly applicable
Yes, I was a bit crude with how I used the words "logical" to "illogical" here. Anyways, I just assumed that because grids lend themselves to a 2D numbering system so well, that every city with a grid layout would use one (the coordinates being split between the numbered street name and the block part of the address), but I was wrong.