Best results for South Barrington Illinois

Sail Lake Michigan for Navy Pier fireworks views on a private charter

Sail Chicago's Playpen with a licensed captain and time to swim

Private sailboat time with Chicago skyline views

Watch the Chicago skyline glow from a private sailboat on Lake Michigan

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

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

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

Paddle the Chicago River after dark with city lights and stories from your guide

Paddle Lake Michigan’s shoreline for city views and guided instruction

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

Paddle the Chicago River and learn downtown architecture in 3 hours

Night kayak tour to watch Navy Pier fireworks

Paddle the Chicago River past the Wild Mile and downtown skyline

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

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

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

Paddle Chicago River routes in a single or double kayak

Paddle the Chicago River in a single or double kayak, from the Wild Mile toward downtown

Build foundational kayaking skills on calm Chicago River waters

Learn essential sea kayaking skills with certified instructors

Learn paddleboard skills for calm-water adventures

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