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I split my donation money evenly between LIB, Active Trans, and my own advocacy projects.
On your stated criteria I'd have to say that Active Trans would edge LIB out by a narrow margin.
I immediately thought of Westtown Bikes as the best bang for the buck in terms of contributing to an effort that's making good things happen before our eyes, but it doesn't really relate to your criteria.
Blackstone Bicycle Works. If you ain't been, put it on the to do list. I'm a tad biased since I worked there for a bit, but these folks are doing so much good in their community. Kids can earn a bike, learn mechanic skills, get real experience in a small business, get homework help, & etc. Not a single day passes without Chris, Aaron, Ty Juan, or their volunteers going above and beyond for these kids. They also sell refurbished bikes and are a full service shop.
I only heard about World Bicycle Relief recently -- I think from a link someone posted here on CL -- but it seems to be doing fantastic things. It's a national/international organization that has given away more than 90,000 sturdy, cargo- and transportation-oriented bicycles to students, healthcare workers and entrepreneurs in sub-Saharan African countries. It was founded and continues to be heavily supported by SRAM, which you probably know is a local company doing great things for bike advocacy in Chicago and far beyond. On the WBR website, check out the inspiring videos.
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