Depends on the structure. As you said, a grain silo is a cylinder. A grain silo is certainly not tall enough to support it (based on my loose guesstimation).

What you're really describing is the various ratios between gravity, buoyancy, and tension required to "pop" a balloon. In the simplest model, you could put each balloon directly on top of the other. Imagine a cylinder which is the perfect width of the balloons. Also imagine, in this special world, that we have an infinitely tall cylinder which is impacted by Earth's gravity regardless of distance. The only thing in the universe is balloons, the cylinder, and Earth. Assuming the cylinder has no mass, the only thing that holds us back is the weight of the balloons. If the "popping" height of balloons is greater than the gravity of earth by some ratio of the weight of each balloon, the air, and the distance from the earth , then it fails to pop. But if it's lower than that, then we can theoretically pop it using the weight of the balloons above it.

I'm just going to guess that - yes - you can pop balloons filled with regular air.