Best results for Water Activities in Naperville, IL

Celebrate, cruise, and swim aboard a 52-foot Sea Ray

Cruise Lake Michigan with a full kitchen, two bathrooms, and skyline views

Ride a Yamaha jet ski across Lake Michigan with views of Chicago's skyline

Paddle Lake Michigan with Chicago skyline views

Paddle Chicago's lakefront with skyline views and basic instruction

Charter a 47’ Carver yacht with kitchen, bathrooms, and Bluetooth audio

Set sail aboard a 50' Sea Ray with a kitchen, bathrooms, and Sonos audio

Cruise a 47-foot Carver with space to relax, dine, and play your music

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

Ride a Yamaha VX WaveRunner across Lake Michigan with Chicago skyline views

Ride Lake Michigan with downtown Chicago views

Private 6–8 hour fishing charter for up to 6 on Lake Michigan

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

Celebrate on the Gypsy Spirit along Chicago’s waterfront

Design your own Chicago lakefront day aboard Soulshine

Ride a new 2026 Yamaha cruiser along Chicago's lakefront