I'd really like to do a move that goes something like:
When you do your best to evade the city guard, roll+Int. On a 12+, count d6 spaces - this is where you find a safety. On a 10+, count d6 spaces - this is where you get a bit ahead of them but you can still hear them searching. On a 7-9, count d6 spaces - this is where they've almost got you. On a miss, count d6 spaces - this is where they've cornered you.
Whenever you roll, cross that place off the list.
1. A narrow alley ending in a short wall
2. A melon cart making it's way through the crossroad
3. A covered market filled with tent stalls.
and so on...
That way once the guard starts chasing you you get to describe the character of the city right off the bat. You could also use it to draw out the path of the chase and then use that as a seed (roads, squares, this is where you run through a house to the next street over, etc.) for mapping the city.