There's a few things I want to get into, some of which are require a separate post, such as my recent visit to San Antonio. But for this one, I want to turn your attention to Chicago.
The first bit of news is the fact that the mayor is setting a policy that requires city employees to take transit instead of city vehicles where possible. This may seem like a policy set to increase transit use, and to degree it is. However, it is primarily a direct response to employees over billing for car reimbursement forms. Things like car washes were being charged to the city.
I really can get behind things like this. For no added expense for the city (unless it does not offer a transit pass as a benefit) or the employee, we find a way to lower city expenses and increase (albeit marginally) CTA's reach.
The other bit of news from the Windy City is they are trying to join the ranks of those cities with congestion pricing. San Francisco instituted an on-street parking program that adjusts rates to demand, a far cry from flat-rate, all-day rate. The region also adjusts toll rates to correspond with demand. London charges a fee to enter downtown by car, something New York considered, but declined to implement.
Chicago is charging a two-dollar surcharge on all public parking. This will increase demand for alternative transport, primarily transit, but also walking biking and a possible land-use change.
I like the principle. I just don't think this is the best way to go. Private parking is completely ignored here, which is usually in abundance and city codes (I don't know Chicago specifically) usually require a large excess. By ignoring the private and regulatory aspect, the effect is blunted. Unless all people are effected equally, the policy will be ineffective at best and useless at worst.
When it comes to congestion pricing, I usually think something is better than nothing, and this is certainly better than the status quo. I just would approach it differently to increase the effect. Maybe that's why it failed politically in New York. Too much change can also be ineffective.