Best century rides in Chicago, IL
Feeling ambitious? These are 100-mile centuries from Chicago — kept flat and paved so it's the distance, not the climbing, that makes the day. Not exactly casual, but a heck of a ride.
‹ Back to casual rides in Chicago
Chicago century out & back ride — 103.83 mi
You're heading out on all pavement with nearly 104 miles and about 529 ft of climbing ahead—a solid endurance loop on quiet roads with minimal traffic. This is a long day in the saddle, so fuel up accordingly and pace yourself for the return journey.
Chicago century loop ride — 115.11 mi
You're looking at a big 115-mile paved loop heading west, with about 1,157 ft of climbing spread across the day—manageable but steady. All pavement, mostly quiet roads with just a short stretch that touches some moderate traffic. Settle in for a long one, but the consistent grade and surface make it a solid all-day ride.