It can be easy to live somewhere and never really understand its scale. I had always felt that way about Chicago. Living on the north side of the city there was a 3-5 mile radius where I spent 95% of my time. That other 5% might have been in obscure corners of the map, but they were all trips made by train. Even if I was 10 miles south and within the city limits, it never felt like I had travelled that far.
One of the only sensible ways to understand the city from this perspective seemed to be to bike it. In my head this felt feasible, I had heard of people who had done the same with New York, which is much less linear, full of creased inlets and bays and so broad stretching across 5 boroughs. Chicago in comparison is straight lines, nearly perpendicular to the lake with a rectangle formed by connecting the south, west, and north sides. After some route estimating on Ride with GPS (which is excellent by the way), I realized that an abridged version of the city route that was optimized for bike routes was entirely possible. So plans were made and a date was set.