Chicago to Milwaukee 4 day Tour by Intrepid Trails offers a chance to seek adventure and scenery from along the Chicago Lake Front Trail, Illinois’ McClory Trail, Wisconsin’s County Bike Trail, Milwaukee’s Oak Leaf Trail as well as lake front roads, historical towns and beaches. We start out in what we consider one of the most fabulous cities on Earth, where some 50 million people visit annually. Riding along Chicago’s Lake Front Trail is something everyone should do; the spectacular skyline, people and attractions make the start and end of our tours most unforgettable. As we continue north on our ride through the Gold Coast, Northwestern University and Glencoe Beach the first day ends right on the harbor in Kenosha. Each Thursday, while in town, sailboat races entertain us will we enjoy a cookout on the deck of the Breakwater Bar and Grill.