Unless it has additional force added, anything in LEO will eventually fall back to earth. There is enough atmospheric drag to cause it to slow down.
For a really good description of Low Earth Orbit, see What’s So Special About Low Earth Orbit?
The question is, where and when will it eventually fall?
See this for a discussion on de-orbiting time frames.
If you want it AIMED at a city, then the applied force to de-orbit it would have to be precisely calculated and methodically applied. It would have to be a controlled reentry. And even then, it would not be a sure thing. However, the time frame could be in hours, if enough thrust were applied to slow it sufficiently. The orbit would effectively be changed from that of an orbiting object to that of a ballistic object - that is, a parabola, as if it were shot like an ICBM from earth. Their targeting can be very precise, but the applied maneuvering thrusts are very carefully controlled.
In point of fact, when vehicles are returning from the ISS, they are sometimes deliberately placed into a steep parabolic ballistic trajectory from their orbital trajectory. See this very technical description, complete with graphs, from NASA, for re-entry trajectories. See particularly figure 2 for a 'Skipping reentry trajectory' - basically, puting it into a parabolic trajectory.
However, if you wanted it to accidentally hit a city, then introduce fate into your story. It is highly unpredictable as to where something will fall. The upper atmosphere is highly unpredictable. But the steeper the descent (the more velocity it looses) the quicker and more predictable the impact point. The more like a ballistic (parabolic) trajectory and less like an orbiting (circular) trajectory. The time frame can be anything from a week to decades, depending on the initial orbit and how much atmospheric drag it comes under.
As for the damage it would cause, it also depends on the impact trajectory and angle of approach. However, if it started from a stable low earth orbit, it would not have gained enough energy to be anything greater than a very big accidental localized collision. It would be similar to a similar sized airplane falling to the ground. It might take out several city blocks, and even leave a trail of destruction if the angle of impact were really shallow, but it would not be a city-buster.
TL;DR
Think of the impact damage of the planes that hit the World Trade Center. They hit under full throttle, and the towers survived initial impact. Scale up the size of the aircraft to match the size of your generation ship, and you have some idea of the scale of the collision. The speed of the falling space ship would actually be somewhat less than the speed of these planes, since the ship would be under free fall, and the planes were under powered flight. And given that generational ships would probably not be aerodynamically shaped, atmospheric drag would be significantly greater than a plane.