things to do in South Barrington, IL

Taste Lincoln Square’s European roots and Silk Road flavors on foot

See Chicago from the water aboard a former Navy tactical boat

Cruise Chicago’s lakefront for skyline and Navy Pier views

A quiet private weeknight sail with Chicago skyline views

Enjoy a weekday farm visit with tickets for just the activities you want to try

Paddle Chicago River routes in a single or double kayak

Pontoon time for fishing, lounging, and pets

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

Discover the artists and history behind West Town’s street art

Stretch, cuddle and take photos with rescue puppies in a private yoga session

Discover the sweeter side of wine this Halloween

Self-drive pontoon on the Chicago River with Navy Pier fireworks

Float above the landscape on a private flight with your group

Taste four Chicago pizza styles on a guided West Loop walk

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

Sail Lake Michigan on a private weeknight cruise with sunset and skyline views

Bring your group together for an autumn outing on the farm

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

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

Jet ski across seven lakes with a guide, from shoreline sights to open water

Save 40% on a midweek team adventure

Slow down with goats, mindful movement, and a guided walk on the farm

Discover the journey from fresh grapes to wine during Chicago's harvest season

Cruise and swim aboard a spacious Sea Ray with room to lounge