You can take a train from Chicago to Alton, IL then ride to the East end of the Katy at Machens, MO. You could get a hotel room in St. Charles, MO or Alton the first night. Research will tell you where camping and lodging places are along the trail. Chicago to Alton is probably a 4-5 hour train ride. You could be on the trail the same day you leave Chicago. The Katy would be excellent in late October. If you haven't been along the river bluffs you should see them. Much more scenic than dead trees and cornfields. I wish I could get time off in the fall, but I am lucky enough to be able to take day trips on the Katy. One of my favorite times to go is mid-winter when the high for the day is below freezing and there isn't much or any snow on the ground.
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