There were three of us hiking last Monday. We started from the Chicago Cultural Center, headed south on Michigan Ave to see the Hilton and the Blackstone Hotel Christmas trees. The weather was unseasonably warm, about 50°F and a bit overcast, but not too windy at the beginning. We then trudged north along Wabash Ave to the Palmer House to see its tree. We ate lunch at the renamed Sterling Food Hall, then headed north past Christkringlmarket (very crowded, even at 1PM), got back onto Wabash to see the Trump Tower tree.
We next stopped at the Peninsula Hotel with a marvelous Christmas tree and lavish Christmas decorations. Next stop was the Bloomingdale building's Christmas tree, then across Michigan Ave to the Drake Hotel, which had a nice tree and a gingerbread Christmas display featuring the Drake.
We walked back south along Michigan Ave, seeing along the sidewalk an interesting Day of the Dead statue and various Nature Museum butterfly statue exhibits, past the Apple Store with its outdoor tree, then back across the Chicago river to see the large, Christmas tree in Millennium Park.
The hike was 5.76 miles, taking 4 hours, including about a 1 hr lunch break.