A traincation I took with friends in 2006:
Monday morning-Took an early Southwest Airlines flight from Midland, TX to Chicago...took an elevated TRAIN to downtown...left our bags at CUS and walked to Lou Mitchell's for lunch...departed on the Southwest Chief at 3:00pm...CB&Q Racetrack, cross the Mississippi at Ft Madison, bedtime after KC Union...Tuesday-see railroad "hallowed ground" of Dodge City, LaJunta, Raton Pass, ABQ, and the red cliffs of Gallup, and Winslow before bedtime. Wednesday morning: Barstow (if you get up early), SanBernadino, Cajon, and LAUPT...take a TRAIN to Bob Hope airport in Burbank...fly back to Midland, TX...home in my own bed Wednesday night.
Best 3 day break from work I can think of.