Chicago Boat Charter with Captain Included
Enjoy an unforgettable day on the water aboard “Loretta”, our classic Hatteras motor yacht. Book a private cruise under the Chicago skyline, tailored to your interests.
Vintage Vibes, Unbelievable Views
EXPANSIVE BOW SEATING
Everyone’s favorite place to sit and take in the spectacular scenery. Enjoy the breeze as you cruise to the Playpen, Monroe Harbor or the Chicago River.
FLYBRIDGE
Interested in a 360 degree view? Spend some time on our flybridge and get a fresh perspective on everything happening around you.
COVERED AFT DECK
Need a little shade? Take a break from the direct sun in our covered cockpit. Ample seating and a capable sound system are at your disposal.
It’s HARD to beat a
SUNSET ON A BOAT
Swim in the shadow of a world-class skyline.
Punch your ticket to the “Playpen”
You’ve heard the name before. You’ve probably inched past it—mired in traffic on Lake Shore Drive—and thought to yourself, “Why am I stuck in this car while all those people are having the time of their lives?”
Trust me, I know from experience. I also know that it’s easier than you think to turn your daydream into a reality. And let me tell you, cruising up to the anchorage in a stunning vintage motor yacht takes the experience to another level. We will drop the hook and roll out the swim mat to allow you and your crew to safely enjoy one of lake Michigan’s most iconic swimming holes.
And for those of you looking for a little less scene and a little more skyline, Monroe Harbor is an excellent choice!
It never gets old.
Cruise the iconic Chicago River
You would be hard-pressed to find a better way to take in the amazing perspective that the Chicago River has to offer. Relax on the bow and wave to people on the Riverwalk as you enjoy view after incredible view. Or join the me on the flybridge for an elevated vantage point. I promise, I’ll let you know when it’s time to duck under a bridge.
There are options for dockage and dining on the river that we can help coordinate to take your trip to the next level.
Light up the night.
Fireworks from the best seat in the (floating) house
Sure, your dog is not a fan. But deep down, you know you still love them. And I can tell you from experience—that awestruck feeling that you had when you were a kid comes flooding back when you see an award-winning fireworks display almost directly overhead.
In 2026, Navy Pier hosts fireworks on Wednesdays at 9pm and Saturdays at 10pm from May 23rd through September 5th. Book your Fireworks Cruise today and look forward to sharing the experience with your closest friends.
Pro tip: a slow cruise through Monroe harbor allows for an up-close view of the incomparable Chicago cityscape prior to taking in the show.
Captain Aaron Grant, USCG 50-ton Master
You’re in good hands
Your Captain has over fifteen years of experience on the water and has been captaining charter boats in the Chicago market for the last five years.
Unlike a bareboat charter, Loretta is 100% owner-operated. I bring all of my personal and professional experience, attention to detail and respect for the water aboard with me for every single trip—this helps ensure that you and your crew can focus on making memories, while I focus on making sure that everything runs as smoothly (and safely) as possible.
Is it Summer yet?
LET’S GO BOATING
Reach out for availability, rates and guidance.