Best results for Chicago Illinois

Private Lake Michigan sailing with swimming, snacks, and a certified captain

Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht

A private sail for proposals, photos, and a champagne toast

Sail Lake Michigan for views of Chicago’s shoreline and skyline

Live blues, Lake Michigan sailing, and Chicago skyline views

See Chicago’s skyline from Lake Michigan on an evening sail

Cruise out for Navy Pier fireworks with skyline views and bar service

90-minute group sail for Navy Pier fireworks and Chicago skyline views

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

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

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