Best 301 things to do in Chicago, IL

Sail Lake Michigan with live blues from Michael Charles and his band

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

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 Lake Michigan’s shoreline for city views and guided instruction

Watch Navy Pier fireworks from a private yacht

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

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

Host a private Chicago event with open-air decks and a professional crew

Set sail on Chicago waters with a captain at the helm

U.S. Coast Guard-certified captain for your Lake Michigan charter

Experienced U.S. Coast Guard–licensed captain for your Sea Ray outing

Bring your group aboard a rented vessel with a 100GT Masters Captain

Explore Chicago’s shoreline with an experienced captain

Tailor a private Chicago boat outing with an experienced captain

Put an expert captain at the helm of your boat

Set out on Lake Michigan with an experienced captain