Originally Posted by donnde

This assumes you really like to walk, also. Start at Willis Tower then walk north on Wacker to the river where it bends east and continue on the north side of the street to Michigan Avenue (this sort of checks off the river walk). Take a right on Michigan and you'll be on your way to the Chicago Cultural Center. Across the street is the north end of Millennium Park. Meander south towards the Art Institute then south-easternly towards Buckingham Fountain. Look for a place to crossover Lake Shore Drive to get to the lakefront path and then head south towards museum campus. After your museum visits you may wish to take a bus or cab north to Navy Pier. When done, walk west on Grand to Michigan (Mag Mile) and then head north which will take you past shopping and to the John Hancock Building (if you didn't do Willis) and Chicago Water Tower. Head back south towards the Orange Line (Randolph / Wabash station) and you've done your list. I would construct this on Google maps to see what the walking time is to determine how much museum time you have and adjust accordingly.