Sketchup has what I believe is one the better/most user-friendly sun shading modelers, for a reasonable $599. I've used it twice now, for two separate mid-rise projects, and it's a great tool.
That being said, 2pm shadows are one thing, but I don't think they will be much of a concern in the afternoon, whether in May or in October, since the shadows will fall more towards the east and not as directly in the park. Late afternoon and early evening shadows cast in Grant Park from along the Michigan Avenue side are more dramatic because the sun is much lower at that point in the west, so even a 15-25 story building can cast a pretty dramatic shadow at 5pm.
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Don't be shy. Step into the light.
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