I recently read Richard Lanyon's Draining Chicago, about the North Branch and the North Shore Channel. Interesting book if you want to learn about the early days of sewage disposal. It deals with the north side exclusively and there are lots of old pictures of the Mayfair Division being built in the area of the Channel as well as the narrow gauge RR used to move the fill from the digging of the Channel.
One of the things that caught my eye was the Chicago & West Ridge Railroad. In this post and the comments below I've attached some maps and the description from the Appendices of the book. Interestingly enough, there is still evidence of this line, as there is rail embedded within Channel Road. Here's a link showing the streetview:
https://www.google.com/maps/@42.0177812,-87.7092957,3a,75y,223.53h,70.22t/data=!3m6!1e1!3m4!1sR0CrWQLZ7Tp4l2_wfaUMEg!2e0!7i16384!8i8192Also in the final PDF is a brief description of the MILW swingbridge onto Goose Island being dislodged and falling into the river.