Small Groups • Up to 13 Guests
Chicago Boat Rentals
for Small Groups
Private yacht charters for up to 13 guests. Whether it's a sunset date, a birthday on the lake, or a casual cruise with friends — we make it easy.
What It's Good For
Built for Intimate Celebrations
Small-group charters are our most flexible option — plan months ahead or lock it in this week.
Date Nights & Sunsets
Glide past the Chicago skyline at golden hour. Intimate, private, and ready when you are.
Friends & Family
Grab your crew and hit the lake. Perfect for birthdays, reunions, and weekend getaways.
Last-Minute Plans
Same-week availability on select vessels. Book today, cruise this weekend.
Bachelorette & Bachelor
Celebrate the big day with a private cruise tailored to your group and vibe.
Why Us
Small Group, Big Experience
Our small-group Sea Rays are bareboat charters — hire a USCG-licensed captain during the booking process, then make the day yours. Bring your own food and drinks, pick your playlist, and swim off the stern.
Our Small Group Fleet
Vessels Up to 13 Passengers
Our Sea Ray fleet — every vessel is a bareboat charter with premium audio, a wet bar, and plenty of space to spread out.
37ft Sea Ray Sundancer
37ft Sea Ray Sundancer
46ft Sea Ray Express
46ft Sea Ray Express
48ft Sea Ray Flybridge
48ft Sea Ray Flybridge
50ft Sea Ray Sundancer
50ft Sea Ray Sundancer
56ft Sea Ray Sundancer
56ft Sundancer 540
Bigger Groups?
We've Got You Covered
Scale up for larger parties, weddings, or corporate events.
Ready to Set Sail?
Book your small-group charter today. Real-time availability on our booking page.