Best results for Water Activities in Chicago, IL

Island tunes, skyline views, and a full bar on the Chicago River

Take in Chicago’s skyline from a floating tiki bar with a full bar on board

See Chicago by water from a floating tiki bar with Sunday drink specials

Cruise Chicago’s waterways aboard a floating tiki bar with Sunday drink specials

Watch fireworks and Chicago sights from a floating tiki bar

Celebrate on a tiki-themed yacht with an open bar and Chicago skyline views

Private 50-foot charter with two decks, a waterslide, and an open bar

Private river cruising with Bluetooth sound and beverage credits on longer charters

Sail Chicago’s skyline aboard an 80-foot tiki-chic yacht

Celebrate on an 80-foot yacht with an included open bar

Private yacht charter with an included open bar and skyline charter option

Cruise the Chicago River aboard a private floating tiki bar

Private Chicago river and lake charter with an included open bar

Cruise Chicago’s river and lake skyline aboard a private two-deck party boat

Private 1962 vintage motorboat cruise on the Chicago River for up to 6 guests

Cruise Chicago’s lake and river on a historic fireboat with docent-led stories

2-hour happy hour cruise with skyline views and a full bar

Paddle Lake Michigan from Ohio Street Beach for two hours

Paddle Lake Michigan for Chicago skyline views

Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board

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

Cruise Chicago’s waterfront with a professional crew and private gathering spaces