Tours And Adventures in Chicago, IL

Watch Navy Pier fireworks from the water with Chicago skyline views

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

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

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

Ride Lake Michigan with downtown Chicago views

Jet ski on Lake Michigan with skyline and Navy Pier views

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

Night kayak tour to watch Navy Pier fireworks

Paddle the Chicago River past the Wild Mile and downtown skyline

Paddle Chicago River routes in a single or double kayak

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

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

Walk Logan Square murals and learn the artists behind them

Sail Lake Michigan on a private day charter with skyline views

Watch Navy Pier fireworks from a private yacht

Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing

Paddle Lake Michigan with Chicago skyline views

Explore Lake Michigan by boat, from Playpen outings to Chicago river cruises

Bring your group aboard for a captain-led Chicago outing

Cruise Chicago’s waterfront with a certified EMT captain

Cruise Chicago with a flexible captain for your 3–4 hour charter

Chart a captain-led Lake Michigan or Chicago River outing tailored to your plans

Set sail on Chicago waters with a captain at the helm