Chicago’s Lakefront trail is without a doubt some of the best biking in the city thanks to the spectacular views, beautiful beaches, and ample opportunities to explore the various neighborhoods of the city. The middle, centered around Grand Ave/Navy Pier, is busiest, so if you are looking to get away from the crowds, stick to the northern or southern portions of the path. For the best views, start at your southernmost point and head north!

Located in the vibrant and proud Puerto Rican neighborhood of Humboldt Park, this open space gained notoriety in 2019 when an alligator dubbed Chance the Snapper found his way into the lagoon. These days the park is gator free, but there is still plenty to see. Rent paddle boats, take the free audio tour to learn about local history, or take a stroll around the peaceful lagoons. There are also areas for fishing, playgrounds for the little ones, and dogs on leashes are welcome to join in the fun.

The Chicago Riverwalk is widely considered one of the star attractions of the city, and it is easy to see why. The path is an ideal spot for a date night, local history tour, or a jog. There are plenty of viewpoints where you can relax and picnic, piers where you can fish or birdwatch, and numerous companies renting boats of all sizes if you feel inspired to hit the water. Try it in the evening and watch the glittering lights come on illuminating this unique blend of nature and urban life.

Walk along the south branch of the Chicago River taking in views of Chicago's skyline and historic bridges from this gorgeous Chinatown park. The loop walk features a blend of Chicago’s industrial buildings, Chinatown’s unique architecture, and the midwestern prairie landscape. The nearby water taxi station makes it easy to get to the park from downtown without fussing over parking. There are also play areas for the little ones, numerous murals to admire, and kayak rentals available onsite.

Located at the site of the old US Steel Plant, Steelworkers Park is a great place to take a stroll along Lake Michigan and the Calumet River. Part of the old steel factory has been converted into a large rock climbing wall where you can test your skills. The park is a peaceful oasis that is rarely crowded, making it a great place for a quiet, short walk on the South Side.

Located on the South Side, with one of the best views of the city, Rainbow Beach Park is a natural gem with an amazing diversity of plant life and 10.2 acres of dune habitat. As you walk through the area, you will see new panne wetlands forming in response to the restoration efforts by volunteers. Playgrounds, a community garden, a fitness center, basketball, tennis, and handball courts are also within the park.

After the Great Chicago Fire of 1871 decimated much of Lincoln Park, the residents got to work rebuilding. Today, Lincoln Park is a fabulous display of Victorian architecture. Visitors to the park can also take advantage of numerous free attractions such as the Lincoln Park Zoo, Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Alfred Caldwell Lilly Pool. Those looking to take a dip should head to North Avenue Beach.