If you don't have eyeballs on your bike at either end of your commute, don't buy a new bike. Plenty of good used bikes in Chicago. No lock will defeat $40 worth of cordless tools.
If the secure storage issue is solved and iF a bike is your only means of transit, other than public, don't skimp too much.
I looked at the Sirrus Sport specs and don't find the Altus/Acera rear derailleurs compelling.
As far as the Trek FX line, I think the $200 up charge for the 7.3 is worthwhile for a more robust component group. Also, when time comes to let go of the bike voluntarily, you'll get at least half the upcharge back.
Last edited by oddjob2; 05-03-16 at 03:42 AM.