I parked my bike by Grant Park, right near the boat dock and began running. Soon I was flying by tourists braving the cold weather at Navy Pier. Took the underground tunnel onto Oak Street and ventured into Old Town. Few things are more enjoyable than multi-tasking. Accomplished a lot of window-shopping while on my run! The high-end stores, like Harry Winston's & Prada, were tastefully decorated for the holiday season. Overall, a very enjoyable run which is arguably why I accidentally ended up running more than I wanted to. Five miles later I was back to my bike.
I, unfortunately, forgot to account for the early sunset. The sun set around 4 and I was left to ride back in the dark. Luckily, my bike is equipped with a light (fun fact: Chicago law requires a light-device on all bicycles after dusk). Although it was a bit chilly, the ride was fairly pleasant. Not a lot of people on the path after October..
Highly recommend taking an "adventure run" sometime. I love Old Town but got to explore so much more on my run. Colorful leaves adorn the quaint townhouses, a true depiction of the beauty of fall. Plus a little window-shopping never hurt anyone..