Best 194 things to do in South Barrington, IL

Paddle Chicago River routes in a single or double kayak

Build foundational kayaking skills on calm Chicago River waters

Paddle Goose Island and downtown as Chicago lights reflect on the river

Cruise Chicago by private 47 ft yacht with space for up to 12 guests

Cruise the Chicago River for 2 hours on a private, self-drive pontoon

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

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

Cruise about two miles offshore for wide-open Chicago sunset views

Speed across Lake Michigan with your own music and skyline views

Cruise the Chicago River for skyline views and Riverwalk sights

Sail Lake Michigan on a private day charter with skyline views

Discover Lincoln Park’s nature and history with a local guide

Fish, lounge, or bring your pet aboard a Lake Elizabeth pontoon

A spacious pontoon with a tiki bar, sound system, and swim ladder

Gather your group for a spacious tiki barge day on Lake Elizabeth

Pontoon time for fishing, lounging, and pets

Cruise Chicago’s lakefront in an exotic vehicle with skyline and landmark views

Feel the raw power of a 707-horsepower American muscle sedan

Cruise Chicago on a 10-mile Lamborghini Urus ride

Feel Porsche handling in an all-wheel-drive electric sedan

See Chicago landmarks from the back seat of a Rolls-Royce with a private driver

Twin-turbo V8 performance with grand-touring comfort

Drive a seven-passenger performance SUV with leather, wood, and all-wheel drive

Twin-turbo V8 performance with a 7-speed automatic transmission