There's four spots on two different streets that cover all passenger trains in town:
1. Canal between Kinzie and Lake covers the Northwestern Station throat tracks and CUS-North throat tracks. (Hi, Builder, Metra MILW, Metra NCS, Metra UP)
2. Roosevelt between Canal and the south branch of the river covers CUS-South (most Amtrak, Metra BNSF, HCS, SWS)
3. Roosevelt between Clark and the south branch of the river covers LaSalle Street Station approach (Metra Rock Island line)
4. Just east of Michigan street, Roosevelt, Adams, or Van Buren cover the approach to Randolph (Millenium) electric terminal for Metra and South Shore trains.
Best to plot out your adventures with google maps using these four spots. When walking from 1 to 2, you can walk through Northwestern station, Boeing building (check the Boeing store), and CUS. Enter NW Station at the Lake overpass, exit the south doors - go back to the riverfront and walk south to the Boeing building. Continue south to the platform entrance for CUS-north, go down the stairs to the platform. Walk south to the waiting rooms, and exit to Canal. head for #2.
The new Acela: It's not Aveliable.