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What are Chicago’s biggest transit mistakes and missed opportunities?

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The city likes to boast about its robust public transit system, but where does it fall short?

Curbed Chicago Flickr pool/Frank G.

Happy Friday dear Curbed readers, it is once again time to have a discussion about Chicago transit. In previous open threads, we’ve discussed themes such as dream transit projects, bike friendliness, whether the Green Line should be extended to Jackson Park, the merits of an O’Hare express line, and just general changes residents would like to see made to the ‘L’ system.

During our first-ever Transportation Week, we focused all things transit and highlighted a number of subjects such as light rail innovation via the Yellow Line, the importance of rail and water to Chicago’s growth and success, getting to and around O’Hare, transformative ideas for Chicago transit, and a walk through the underground Chicago Pedway system.

But let’s take today’s open thread as an opportunity to discuss where the city has fallen short. There’s always going to be room to improve, but there are certainly some key mistakes and missed opportunities that we’re all aware of. What do you think are some of the biggest shortfalls or missteps in Chicago’s urban planning and transit structure?