Any long distance trip on AMTRAK seems to end in Chicago (at least for us West Coast types). If you are changing trains, chances are you will do it in Chicago.
This is actually a good thing. Union Station Chicago is right in the loop, so you are close to public transportation (if needed) and hotels. Food can sometimes be a problem (especially on the weekends) so I suggest if everything is closed, head to Giordano's Pizza at 223 West Jackson Blvd. It is about 3 blocks from the station at the corner of Franklin and Jackson. We have actually used it when we are between train arrivals and departures. It is not cheap, but it is always available and the food is great.
The reason why trains depart and arrive in Chicago is because of the history of our rail transportation. Most rail was built in the late 1800's after the Civil War. The Great Lakes, stockyards and grain were in Chicago and neighboring states and so moving things around the rest of the Country hinged on Chicago.
A hint if you are scheduling a transfer in Chicago. If you are in a sleeper car, either Roomette or Bedroom, you can use the Metropolitan Lounge at Chicago, to rest between trains, get a snack or check your bags so you can explore the station or the downtown area adjacent to it.
We have walked to our hotel, but it is very easy to get a taxi outside the station. Follow the signs inside the station to the Canal Street exit. You will see a whole line of taxi's and an attendant to help you. The cost is fixed at $3.25 plus tip.
A true blessing after a tiring trip.

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