Chicago Lakefront and Route 66 Loop

While the route combines the iconic Chicago Lakefront Trail with the beginning segments of historic Route 66, it is not a formally designated single loop trail. Touring cyclists typically start with the Lakefront Trail and then transition to Route 66. A return to Chicago to complete a 'loop' would require planning a separate return journey or using alternative transportation.

The route effectively begins along the Chicago Lakefront Trail, offering immediate scenic views. The official starting point of historic Route 66 is nearby, at Adams Street and Michigan Avenue in downtown Chicago, which is easily accessible from the Lakefront Trail.

The Chicago Lakefront Trail section is an 18.5-mile paved path that is predominantly flat, with only occasional slight inclines. The Illinois portion of Route 66 also features mostly flat to gently rolling terrain, typical of a prairie landscape, often utilizing dedicated bike trails or quiet rural roads.

Along the Lakefront Trail, you'll enjoy stunning views of Lake Michigan and the Chicago skyline, passing landmarks like Navy Pier and Museum Campus. You'll also cycle past the View of downtown Chicago from the Shedd Aquarium and the Field Museum. The Route 66 segment offers a nostalgic journey through Americana, with open farmland, quaint towns, and classic roadside attractions, including the Beginning of historic Route 66.

Yes, this route is generally considered easy. Both the Chicago Lakefront Trail and the Illinois segment of Route 66 are characterized by mostly flat terrain. The main challenge on the Lakefront Trail can be congestion, especially on weekends, but dedicated lanes help manage this. The Route 66 portion is relaxed and rewarding due to its gentle terrain and often lightly traveled roads.

The best time to cycle this route is typically from late spring through early autumn (May to October). During these months, the weather is generally pleasant for cycling, and all attractions are usually open. Summer weekends can be busy on the Lakefront Trail, so consider weekdays or earlier mornings for a quieter experience.

No, you do not need any special permits or pay entrance fees to cycle the Chicago Lakefront Trail or the initial segments of Route 66 in Illinois. Both are publicly accessible. However, individual attractions you might visit along the way, such as museums, may have their own admission fees.

Dogs are generally allowed on the Chicago Lakefront Trail, provided they are on a leash. For the Route 66 segments, rules can vary depending on specific towns or parks you pass through, so it's best to check local regulations if you plan to bring your dog. Always ensure your dog is well-behaved and you clean up after them.

The Chicago Lakefront Trail can get very busy, especially on weekends and during peak hours. To avoid congestion, consider cycling during weekday mornings or early evenings. The trail has separate lanes for cyclists and pedestrians, which helps, but being aware of your surroundings and riding defensively is always recommended.

Yes, the route incorporates sections of several official trails. Notably, it utilizes significant portions of the Lakefront Trail and also passes through segments of the Grand Illinois Trail - Maywood to Lansing and the historic Route 66 itself. Various city bikeways like Dearborn Street Bikeway and Harrison Street Bikeway are also part of the overall experience.

Yes, Chicago offers numerous bike rental services, particularly in the downtown area and near the Lakefront Trail. You can find several shops that rent touring bicycles, and the city's Divvy bike-share system also has stations conveniently located throughout the area, including near the Lakefront and the start of Route 66.

Along the Chicago Lakefront Trail, you'll find numerous facilities including restrooms, water fountains, and concession stands, especially near popular beaches and parks. As you transition to Route 66, you'll encounter cafes, diners, and local businesses in the small towns, offering opportunities for food, drinks, and restrooms. It's always a good idea to carry some water and snacks, especially on longer stretches.