Why choose Two Brothers Sailing adventures when you are looking to charter a boat in Chicago? Because you can trust us for Chicago Boat charters or whatever you’re looking for in your sailing trip, we can give it to you. We pride ourselves on tailoring each charter boat experience to the unique desires of all our passengers. 

One of our favorite things about our job is watching our customer’s dream come to life. Whether that’s planning the perfect proposal, family reunion, or a team building experience with coworkers, we make sure your next boat charter or sail in Chicago is exactly how you pictured it.

If you want a romantic, gourmet meal catered from one of Chicago’s finest restaurants, we’ll take care of the booking. Or, if you prefer, you can bring your own food. When you step aboard one of our charters, you call the shots.

Never been sailing, and not sure what type of experience you would like? Let us share some of our most popular requests.

Romance, a Captain favorite:

“I love the fact that there’s no motor. It’s quiet, peaceful and romantic.” “It’s nature pushing us not a motor — it’s very romantic.” — Captain Jeff

We love helping our passengers plan the perfect date. We have helped coordinate everything from engagement proposals to anniversaries, and every time it has proved to be something special. You tell us what you want, and we’ll take care of the rest, so you can enjoy a candlelight dinner for two on the dock.



Nothing beats the look of Chicago’s skyline at sunset. That’s why it’s one of our most requested times to rent a sailing charter. It’s the perfect setting for a romantic getaway, or spending time with loved ones.


Whether you’re visiting Chicago for the weekend, or have been living in the area all your life, setting sail along Lake Michigan and soaking in the sites is timeless. We can take you along downtown to see Navy Pier, the water cribs, and so much more.


If you’re looking for something a little more turned up, we’ve got you covered. So invite all your friends and step aboard any one of our sailboats for the ride of your life. Besides, who said speed boats get to have all the fun?
At the end of the day, we’re a people that loves the art of sailing, and we hope to share that passion with you. Give us a call today and book your next Chicago sailing adventure. We look forward to providing you with the exact luxury charter you desire.