Hotels near The Lakefront Trail

The Lakefront Trail runs 18.5 miles along Lake Michigan from Ardmore Avenue in the north to 71st Street in the south, entirely on public land, because Chicago's 19th-century planners kept the shoreline out of private hands. It was separated into parallel cycling and pedestrian paths a few years ago, which removed the main reason people used to avoid it. The stretch from Oak Street Beach south to the Museum Campus is the classic one.

October is when this becomes the best walk in the city. The skyline view from the curve at Oak Street Beach works better in clear autumn air than in summer haze, the trail empties out, and the trees in the parks alongside turn through the second half of the month. Divvy bike share docks sit along the length of it. Take a windproof layer, because the lake wind is a real thing and there is no shelter.

Pro Tip: Walk or cycle north to south in the late afternoon. The skyline sits in front of you the whole way rather than behind, and finishing at the Museum Campus around sunset gives you the postcard view of the city from the Adler Planetarium point.