u/looneybabyblue

hi all! i am looking at booking a trip on the empire builder in early october heading eastbound from seattle - chicago. currently, all tickets show this route arriving around 4:45pm in chicago. in general, would booking a flight from ohare for 9:15pm be possible, or should i spend the extra money for a hotel for a night in chicago and fly home the next day just to be safe? thank you in advance!