Tourists and even Northside and Westside Chicagoans forget or don't know how far South they can ride on the Lakefront trail. Start at the Lake Front Trail across the street from Buckingham Fountain. Head South (trust me it is 75% less crowded than heading North). Pass by the Planetarium. Ride under the viaduct and get your peddle on. You'll pass the beautiful fountain and feel the mist at McCormick Place on your left and the lake is steps away on your right. Pass the beautiful 31st street beach or stop for a jet ski, paddle board or snack. Continue past 57th Street Beach then past the gorgeous historic voluminous 63rd St Beach House ( it is a stop for pics moment) and continue until you reach the South Shore Culture Club. Stop for a swim or snack. 16 miles roundtrip.