There are many reasons to run on the Lakefront Trail: the great views of the lake and city, the calm and peaceful atmosphere, the fresh air, and the motivation brought about by sharing the trail with many other runners and cyclists. Stretching for over 18 miles (28.9 kilometers) from Edgewater to South Shore, mile markers make it perfect for tracking both short and long distance runs, and it’s so long that you can mix up which sections you use each time.
The Lakefront Trail, Chicago, IL, USA, +1 312 742 7529
The North Shore Channel Trail is quieter than many of these routes due to its location further out of the city, and there are many other reasons to try it. Starting in Ravenswood and running all the way to Evanston, 6.7 miles (10.8 kilometers) in total, woodland-surrounded sections of the path provide shelter from both the sun and the wind, and there are plenty of water fountains in parks along the way.