Best 194 things to do in South Barrington, IL

Take to the water on a 21-foot pontoon

Relax on a captain-led pontoon outing with room for your crew

Ride past Chicago’s lakefront landmarks by jet ski

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

Eat Chicago’s five classic dishes with VIP access in River North and Streeterville

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Eat your way through Chicago’s Chinatown with 5 seated tastings

Sail Lake Michigan for Chicago skyline views and Navy Pier fireworks

Sail Chicago’s lakefront on a private charter with time to swim and relax

Sail Lake Michigan with Chicago skyline views

Sail Lake Michigan at sunset for Chicago skyline views from the water

Build practical sailing skills aboard a 26-foot Chris-Craft on Lake Michigan

Choose your paddlecraft for a self-guided outing on the water

Explore Chicago River routes by kayak or stand-up paddleboard at your own pace

Learn paddleboard skills for calm-water adventures

Sail Chicago's lakefront from Museum Row to Navy Pier at sunset

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

Choose solo, tandem, or stand-up paddling for a flexible lake outing

Paddle the winding DuPage River past Naperville's quiet corners

Pilot a 2-person Craig Cat and cruise the Chicago River skyline

Paddle past the Wild Mile and Chicago's skyline in a single or double kayak

Cruise Chicago’s river in a vintage 1950s Milo Craft

Paddle the Chicago River and learn downtown architecture in 3 hours

Paddle the Chicago River past the Wild Mile and downtown skyline