Bike parking at the bottom of Marquam Hill, where the Portland Aerial Tram meets the Portland Streetcar. I think Portland is one of the most multi and inter-modal cities in the United States.
To get to this spot from Chicago, without a car, I would:
1. Ride a bicycle to Union Station in Chicago and lock it up.
2. Take the Amtrak from Chicago Union Station to Portland Union Station.
3. At Portland Union Station, board the MAX light rail, Green or Yellow line.
4. Transfer from the Green or Yellow line to the Portland Streetcar at Portland State University (PSU) Urban Center stop.
5. Take the Portland Streetcar south to South Waterfront District.
I could then hop on the Portland Aerial Tram and head up the hill to Oregon Health Sciences University. You might be a researcher at University of Illinois at Chicago and you need to give a presentation at OHSU.