Many consider Chicago’s lakefront one of its greatest attractions.

The lakefront has a lot to offer, including many beaches, nature reserves and sporting amenities. Some of Chicago’s most venerated cultural institutions and museums also reside along the shores of Lake Michigan.

For the bicycling enthusiast, the significance of the lakefront cannot be overstated. Over twenty miles of lakefront pathways connect the south and north sides of the city. This also makes it easy and enjoyable to discover a wide variety of Chicago’s unique neighborhoods.

Additionally, many bike lanes connect directly to the lakefront pathway or lie in close proximity to it.

While there are many popular places to visit along the lakefront, the following is a guide to some of the more tucked away and interesting places. Other listings are significant works of architecture or sculpture.

Northside

“I Will” by Ellsworth Kelly | Fullerton Avenue
Just off the lakefront trail, the Ellsworth Kelly sculpture is situated just to the west of Lake Shore Drive. The sculpture by the renowned modernist is a tribute to the development of the Chicago skyscraper.

In the shadows of the field house is the Clock Tower Café that serves lunch and cocktails. The restaurant is a perfect place to relax after a long day of riding.

Montrose Harbor

The Sanctuary is nestled in a wooded alcove at the outer point of Montrose Harbor along the edge of Lake Michigan. Many acres of the natural prairie reserve and wetland area attract a wide variety of interesting and unique bird species as well as bird watching enthusiasts.

Montrose Dunes is a newly cultivated protected area and bird sanctuary that restores a small part of the Lake Michigan shoreline to its natural setting. It should be noted that bicycles are prohibited in the Dunes area and bike racks are located close by.

The Changing Room structure is a wonderful architectural relic from the Art Deco age that draws its inspiration from streamlined ship designs.

Osterman Beach (AKA Hollywood Beach)



Hollywood Beach, especially at non-peak hours, offers a quiet lakefront retreat with a lot of robust wave activity and a sweeping view of the far northern edge of Chicago’s skyline.

Lincoln Park Conservancy and the Alfred Caldwell Lily Pool | 125 West Fullerton Parkway

Just beyond the Kelly sculpture, the Conservatory and Lily Pool offer great escape from the busyness of the lakefront on weekends and holidays. A beautiful lily pool and surrounding landscape make this one of Chicago’s best tucked away places.



Also, several shelters designed by Caldwell are superb examples of Chicago Prairie School architecture at its best.

Downtown

Several of the following buildings in the downtown area along the lakefront are some of the most icon and important structures of 20th Century design and architecture.

860 and 880 North Lake Shore Drive
Designed by Ludwig Mies Van der Rohe, these International Style towers are the first modern steel and glass skyscrapers in the world.

Lake Point Tower | Grand Avenue and the Lakefront

This curvilinear International Style residential building takes its inspiration from an earlier Mies van der Rohe designed, but unbuilt, structure. Architects John Heinrich and George Schipporeit are the architects of this Modern edifice.



McCormick Place

McCormick Place is another steel and glass architectural masterpiece along Lake Michigan. Designed in the early 1970s by architect Gene Summers of C. F. Murphy and Associates, McCormick Place is one of Chicago’s most important works of modern architecture.

Southside

Lakefront Prairie | East 47th Street and Cornell Drive
A beautiful and tucked away prairie and wetland area with trails and observatory areas.

Jackson Park | South 56th Street to 67th Street and the Lakefront

Once the site of the 1893 World’s Fair, The Columbian Exposition, Jackson Park offers endless amounts of interesting things to discover, including Japanese gardens.

South Shore Cultural Center | 71st Street and South Shore Drive
Once an Edwardian Age country club, now part of the Chicago Park District, this is a place not to be missed. The former clubhouse and pleasure grounds offer a glimpse into how the elite and upper classes of a bygone era once lived.



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