The 25-mile bike path primarily follows the route of the Chicago North Shore and Milwaukee Railroad, which expanded all the way to Milwaukee in 1919 as an electric interurban freight and passenger railroad. It ceased operations in 1963 after ridership declined. The trail also uses low-traffic city streets. A Metra commuter railway connects Chicago to Kenosha, Wisconsin, on Union Pacific Railroad tracks that parallel much of the trail.
Start the day with a cup of coffee in hand and your feet in Wisconsin, just a short hour drive from Palatine. You start your ride into the dark knowing the sunrise is minutes away. Pass through or by Winthrop Harbor, Zion, Illinois Beach State Park, as you make your way to the Green Bay Trail. Continue south, Sheridan Road to your left, The Botanic Garden to your right. Ride from Glenco to Kenilworth with shops, parks, restrooms all the way. Next The North Shore Channel Trail, Some may think this is the best park of your journey. About halfway you'll pass through Lincolnwood Centennial Park the perfect place for lunch. Finally pick up the Chicago Lakefront Trail at Montrose Beach. 19 miles of lakefront and many amenities. North Avenue Beach, OakStreet Beach, Navy Pier, Millennium Park, Buckingham Fountain, Grant Park, The Shed, The Field, Solder Field, you'll see them. Keep going, your day is almost done. 31st Street Beach, Burnham Park Fitness Station, Morgan Point, Promontory Point, 63rd Street Beach and end at South Shore Nature Sanctuary.
The 9-mile Green Bay Trail runs parallel to Chicago's Metra commuter rail line north of the Chicago city limits. Stretching through North Shore towns such as Kenilworth, Winnetka, Highland Park and Lake Bluff, the corridor is flanked by restaurants, shops, community parks and beautiful homes. Because the trail stays generally within a mile of Lake Michigan, you can take any number of on-road side trips for beachfront views of the lake.
The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago and passing many cultural and tourist attractions throughout the city.
The North Shore Channel Trail extends from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in Chicago. All but the last 0.25 mile runs alongside the North Shore Channel, a drainage and aeration canal built in 1909; the last 0.25 mile follows the North Branch of the Chicago River.
For most of the way, a trail occupies both sides of the North Shore Channel.