easy
3 hours
Suitable for most fitness levels, no prior experience needed
Set sail on a luxurious Chicago lakefront cruise and enjoy breathtaking city views from the water. Whether relaxing, swimming, or sightseeing, this private boat experience offers a unique perspective of the Windy City.
Relax & Breathe In The Beauty of Lake Michigan With This 3-Hour Sip & Sail Adventure!
Experience the thrill of a private 3-hour lakefront cruise aboard a luxurious 37' sailboat in Chicago. With a USCG-certified captain, you can choose your adventure—sail, swim, or simply relax. Enjoy complimentary snacks and beverages while soaking in stunning city views from the water. An unforgettable sailing experience awaits!
Our private Chicago Lakefront Cruise will take you & your guests on a favorable sail along the gorgeous Lakefront, giving a unique perspective on the city's world-class architectural landscape. Want to take the helm, jump in the Lake or just relax on deck to the sound of wind and waves? We provide a choose your own adventure. If you're looking for an intimate way to experience sailing in Chicago - this is the cruise for you.
✅ USCG-Certified Captain trained in First Aid and CPR.
✅ Private use of our fully-permitted, fully-insured sailing yacht.
✅ Complimentary beverages and snacks on board.
✅ Fully stocked kitchenware, fridge and bathroom.
✅ Stereo surround sound speakers with Bluetooth connection.
✅ Swim platform with ladder, life-jackets, noodles, floaties & towels.
❌ NO Separate captain fee
❌ NO Fuel and docking fee
❌ NO Damage/cleaning deposit
We do our best to have on board everything you might need, some personal items to keep in mind include:
You may bring any food and beverages of your choosing including beer, wine, champagne, or hard seltzers. We have alcohol for purchase on board or ahead of time and can provide catering for an added fee.
If there is current or forecasted lightning or high wind, we make a weather cancellation one hour before your scheduled departure and provide a full refund.
You can see all of our FAQs here on our website
On A Boat Sailing, LLC
info@onaboatsailing.com
312.619.7858
Apply sunscreen and wear protective clothing to stay comfortable during the cruise.
Arrive 15 minutes before the departure time for smooth boarding and some time to relax.
Drink plenty of water, especially on warm days, to stay energized.
Bring a swimsuit if you plan to swim, and consider bringing a towel.
The Chicago Lakefront has been a vital part of the city's development since the 19th century, serving as a hub for recreation and transportation.
The cruise operators participate in local water conservation efforts and promote eco-friendly practices to protect Lake Michigan’s ecosystem.
Protect your skin from sunburn during the cruise.
summer specific
Shield your eyes and face from direct sunlight.
summer specific
Optional for swimming or water activities.
summer specific
Stay hydrated throughout the cruise.