The Chicago Department of Transportation has a cool tool you can use to request new bike racks.
Racks need to be on a concrete surface at least 10 feet wide. CDOT also won’t install them in purely residential areas either.
This is just a picture. Click here for the actual site.
You can see where people have requested new racks, and also where CDOT has rejected new rack requests.
More important, you can see the human drama of the rack request process.
A sad story from a lady who keeps hitting her head on the racks at 95th (on CTA property, unfortunately):
Lake Point Tower illegally threatening people who lock their bikes to street signs:
Sleazy stuff.
You can also report abandoned bikes using a similar tool on the Complete Streets site.
Chicago Bike Report 