Promontory Point

Promontory Point is the Chicago skyline viewpoint that locals keep to themselves. This man-made peninsula juts into Lake Michigan from Hyde Park, and the panoramic view of downtown Chicago from across the water is genuinely spectacular — arguably the best skyline view in the city, and it is completely free. While tourists pack Navy Pier and the Skydeck, families who discover the Point get an uncrowded, natural setting with views that rival any paid attraction.

The point was built in the 1930s as part of the Burnham Park lakefront improvements. Its defining feature is the limestone block shoreline — large, flat-topped rocks that step down from the grassy hillside to the water's edge. For kids, these rocks are irresistible.

They scramble, climb, hop from rock to rock, and explore the crevices where the stones meet the water. The rocks are stable and large enough to be safe for older kids, though parents should supervise young children near the water. This kind of unstructured, natural play is increasingly rare in urban settings, and kids respond to it immediately.

The sunset experience is the real draw for families. Arrive an hour before sunset, spread a blanket on the grassy hillside, and watch the sky change colors behind the Chicago skyline. As daylight fades, the buildings begin to light up — first a few office towers, then the whole skyline glowing against the deepening sky.

It is the kind of simple, no-cost experience that becomes a core vacation memory. Bring a picnic and make an evening of it.

In summer, the Point has a designated swimming area with a stone beach. The water is Lake Michigan — cold and fresh — and the rocky entry requires water shoes. There are no lifeguards at the Point itself (the nearby 57th Street Beach has lifeguards), so swimming is at your own risk. For many families, wading and splashing along the rocky shoreline is enough water play without full-on swimming.

The Point is in Hyde Park, one of Chicago's most interesting neighborhoods. The University of Chicago campus is a few blocks west. The Museum of Science and Industry — one of the best science museums in the country — is a 10-minute walk north along the lakefront path. Combining a morning at MSI with an afternoon picnic at the Point makes for a perfect full-day itinerary.

Parking is free along DuSable Lake Shore Drive. The Point is a 20-minute drive from downtown Chicago. By CTA, take the 6 Jackson Park Express bus or the Metra Electric line to the 55th-56th-57th Street station. The area is safe and well-used by families, runners, and University of Chicago students.