things to do in South Barrington, IL

Eat your way through Uptown’s immigrant neighborhoods in 2.5 hours

See Chicago landmarks from the water on a private sightseeing outing

Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water

Sail Lake Michigan with Chicago skyline views

Look beyond the brickwork to uncover a neighborhood's surprising stories

Paddle the Chicago River past the Wild Mile and downtown skyline

Take the wheel on a 22 ft pontoon cruise on the Chicago River

Build sourdough skills and take home starter, bread, and dough for your next bake

Sail Lake Michigan on a private day charter with skyline views

Stretch, cuddle, and play with rescue kittens in a 1-hour indoor class

See Chicago landmarks by helicopter with a 5-passenger twin-engine aircraft

Explore Lake Michigan’s quieter shore, from lakeside towns to grand mansions

Taste Vietnam, the Middle East, and Sweden while exploring Argyle and Andersonville with a guide

Photograph Chicago's skyline from a US Navy-built boat

Private Lake Michigan fishing with an expert crew

Share a peaceful Lake Michigan sail with Chicago skyline views

Discover the many lives of Wicker Park through its bricks and buildings

Paddle the Chicago River and learn downtown architecture in 3 hours

Taste Mexican cuisine and discover Pilsen’s mural-covered streets

Take to the water on a 21-foot pontoon

Watch Navy Pier fireworks from a private yacht

Host a private kitten yoga party with playtime at The Arboretum of South Barrington

Private 6–8 hour fishing charter for up to 6 on Lake Michigan

Explore the history, neighborhood culture, and presidential ties of Chicago's South Side