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.
Upcoming on the Water
Chicago's best moments happen on the lake. Book a charter around these events.
Memorial Day Weekend
Kick off the Chicago boating season in style. Memorial Day Weekend marks the official start of summer on Lake Michigan. The harbors come alive, the Playpen fills up, and the city moves to the water. Charter a yacht and start the season the way it's meant to be.
Book a charter →Black Scene
Chicago's premier Black boating and entertainment celebration. Black Scene brings hundreds of boats to the Playpen and lakefront for a day of music, community, and unforgettable energy on the water. Charter your own yacht and cruise through the heart of the action with a front-row view from the water.
Book a charter →July 4th Weekend
Celebrate Independence Day from the best seat in Chicago. July 4th Weekend is the most sought-after charter weekend of the summer. The lakefront is alive, the harbors are packed, and the skyline has never looked better from the water. July 4, 2026 falls on a Saturday, so the regular Navy Pier fireworks at 10 PM will be happening that evening.
Book a charter →Black Yacht Weekend
One of Chicago's biggest boating weekends. Black Yacht Weekend brings hundreds of boats to the Playpen and lakefront for a weekend of music, culture, and community on Lake Michigan. Charter your own yacht and cruise through the energy with unmatched views from the water.
Book a charter →Chicago Scene Boat Party
The biggest boat party in Chicago. Chicago Scene brings hundreds of boats to the Playpen for the single biggest day on the water all summer. Charter your own vessel, bring your crew, and cruise through the scene with the best views on the lake.
Book a charter →What our guests are saying
“Lola was absolutely amazing! We were so thankful for the patience and kindness she showed. She was so engaged and excited, even with our small class. Was an amazing first experience”
Isabella Hedquist
7 months 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
a year ago
“Had the time of my life at the playpen last night for Sunset 🤩❤️🔥🥂 unreal views!! I can’t wait to go back!!”
Rocio Ferrantella
11 months ago
Earn with your boat
Founding Fleet: 0% commission on your first 3 completed charters. 30 spots.
Join our captain network
Clear trip details, reliable scheduling, and steady access to vetted charter opportunities