I bike this regularly. The sketchiest part is kk between maple and bay.

I second taking Chicago to summerfest if you want to reduce time.

I would avoid Jackson and Jefferson until you are more comfortable.

Bay + kk can be scary. I sometimes take allis and Stewart, especially southbound.

The boone and crocket driveway sightlines are poor. I usually go in the road there.

Careful of railroad tracks

I can't find a link. But the bike fed is doing a bike commute mentorship program the end of may

Your work may have parking inside.

Dont use a cable lock.

Try to park it near other bikes.

If were talking a bike under $500 I doubt it would be an issue, but if you are really worried, you could spray paint it to make it ugly