B&O CT and SCAL had adjacent bridges (built over dry land as the river was being rechanneled in 1927-29) and ran side-by-side from there west to at least Halsted (with a team track in between). With the railroad ROW at both ends now sold off, I'm not sure what will become of the B&OCT bridge.
As for the SCAL, I've never gotten a satisfactory answer as to why the city feels the need to move the railroad off of it. Bill Wendt sneers at "yuppies" complaining about it, but I've never been to a meeting where it was even brought up. Perhaps the trains squeal on the curve at South Y Junction, next to Central Station, and those folks complain to their mayoral neighbor.
I think the intent would be to keep it as an elevated greenway, like the Bloomingdale Trail. But the connection (further south) that would allow the railroad to abandon it is part of the still-unfunded CREATE plan. I wouldn't make plans to bike there next summer.
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Imagine how many would-be commuters would opt for bike transit if they were given a straight-shot means of commuting
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Oh, about 120 more than do so now. The north and south lakefronts already have such a path, and the modal split for bikes is less than rounding error.