See the skyline from the water
Private yacht charters and boat rentals in Chicago
Birthdays, proposals, corporate events, fireworks, river cruises
What are you planning?
Have questions? Contact Us
Weather Protection
Flexible rescheduling and refund options when Chicago weather has other plans.
Guaranteed Departure
Your charter departs on time or you receive a full refund — no exceptions.
Credential-Verified Captains
Every captain is USCG-licensed and vetted by our maritime safety team.
Transparent Pricing
The price you see is the price you pay. No hidden fees, no fuel surcharges.
What’s the occasion?
Birthday Cruise
Celebrate another year on Lake Michigan.
Bachelorette Party
The ultimate send-off on the water.
Corporate Event
Impress clients with skyline views.
Proposal Cruise
Pop the question against the Chicago skyline.
Family Outing
Quality time, open water, zero screens.
Date Night
An evening they will never forget.
Sunset Cruise
Golden hour from the best seat in the city.
Fireworks Viewing
Front-row seats to Navy Pier fireworks.
Friends & Good Times
No occasion needed. Just good people and open water.
Featured vessels
View all boats →
Three steps to your perfect charter
Browse & Choose
Pick your occasion and explore our curated fleet. Filter by guest count, date, and budget to find the perfect vessel.
Book & Customize
Secure your date with transparent pricing. Add catering, decorations, or special requests to make it yours.
Board & Enjoy
Arrive at the dock, step aboard, and let your captain handle the rest. All you have to do is enjoy the skyline.
What our guests are saying
“Great place to drop anchor and enjoy the day.”
Kevin
4 weeks ago
“One time as we sailed by the playpen, my mom shouted, “look! A boat full of bikini babies!”. Scarred for life and will literally never be the same. Quality urban agua spot, still.”
Russell’s Reviews
a month ago
“Had a blast yesterday with the Nautichicago team at the playpen chicago! Summer is here. Be sure to head out to the playpen because summertimechi is the best!”
Edwin Medina
2 years ago
Earn with your boat
Founding Fleet: 30 spots, recognition badge, priority onboarding, and an advisory-board seat for Chicago’s launch cohort.
Join our captain network
Clear trip details, reliable scheduling, and steady access to vetted charter opportunities