Chicago’s skyline isn’t just a backdrop for city photos — it’s a view best appreciated from the water. The Windy City’s lakefront location, combined with its iconic architecture and lively waterfront scene, makes it a perfect place for sailing. Whether you’re seeking a private escape, a luxurious day on a catamaran, or a flexible charter for special occasions, Chicago offers a variety of sailing experiences that cater to different tastes. We especially like the Private Sailing on Lake Michigan for its personalized touch, and the Private Catamaran for larger groups wanting a more indulgent outing. These tours provide an authentic way to see the city from the water while enjoying tailored service and stunning views.
If you’re after an intimate, customizable outing with expert guidance, the Private Sailing on Beautiful Lake Michigan from Navy Pier (More Info) is a top pick. For those who want to indulge in luxury with plenty of space and amenities, the Chicago: Private Catamaran Sailing (More Info) offers a large, comfortable vessel perfect for groups up to 12. Finally, for a more traditional, leisurely yacht experience, the Chicago Private Rental Yacht Charter (More Info) provides a flexible schedule designed for unforgettable moments on the water.
1. Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago
At number one, this private sailing tour offers a personal escape on Lake Michigan with the full attention of your captain. You and up to five friends or family members will enjoy the exclusivity of a private sailboat, with a duration of around 2 hours. The trip departs from Navy Pier Marina, a lively Chicago landmark, and takes you past the Grand Ballroom, the Adler Planetarium, and the shimmering skyline.
What sets this experience apart is its fully customizable itinerary. Want to sail past certain landmarks or include some music? No problem — just let your captain know. The boat is equipped with Bluetooth, so you can play your favorite tunes while enjoying the breeze. The reviews speak volumes: “Captain Mike was awesome, time flew by,” says one happy sailor. Many highlight the intimate setting and the chance to take the helm if you’re feeling adventurous.
Bottom line: this tour is perfect for couples celebrating special occasions or anyone looking for a personalized day on Lake Michigan. It’s a bit pricier but offers a tailored, private experience that’s hard to match.
2. Chicago: Private Catamaran Sailing for up to 12 people
Number two on our list is the luxurious private catamaran designed for larger groups. This tour includes Chicago’s largest chartered catamaran, making it ideal for family reunions, corporate outings, or just a big group of friends. The vessel features upscale amenities to keep everyone comfortable — think sunbathing nets, shaded areas, and a spacious deck. The sail lasts between 2 to 4 hours, offering plenty of time to soak in the breathtaking skyline and enjoy the refreshing waters.
One of the biggest draws here is the opportunity to swim, relax, and indulge in the luxury of private yachting. Watching the sunset from this vessel creates a serene, reflective atmosphere that many find unforgettable. While specific reviews are not provided, the focus on amenities and size indicates this is best suited for groups wanting a more indulgent, social experience. The price reflects the luxury level and capacity, making it a worthwhile splurge for special occasions.
Bottom line: this is your choice if you’re traveling with a larger party and want a high-end, customizable experience with the chance for swimming and sunset views.
$1,500 per group up to 13
3. Chicago Private Rental Yacht Charter
Topping off our list is the Chicago Private Rental Yacht Charter, which offers a luxury, flexible experience on the water. It’s perfect for those wanting to customize their schedule and enjoy a luxury vessel with plenty of space. The rental costs around $700 per group, accommodating up to 12 people, with durations ranging from 3 to 8 hours — ideal for extended outings or special events.
This experience is tailored to your desires, whether that’s a leisurely cruise, a celebration, or just a day of relaxing on the water. The captain’s fees are separate, giving you the freedom to craft your ideal itinerary. While this tour has no reviews yet, the focus on luxury and customization makes it appealing to travelers seeking a bespoke boating experience. It’s also a good option if you’re planning a longer, more leisurely day or special event.
Bottom line: this charter suits travelers who want a personalized experience, with the flexibility to set their own schedule and enjoy a luxury yacht.
$700.00 per group (up to 12)
How to Choose Your Perfect Chicago Sailing Experience
When selecting a sailing tour, consider your budget, group size, and what kind of experience you’re after. For a romantic or intimate outing, the private sailboat offers a personal cruise with the option to customize. If you’re traveling with a larger group and want to indulge in luxury, the catamaran delivers comfort and space for everyone, including swimming and sunset views. For those who prefer complete flexibility and a luxury setting, the yacht charter is an excellent choice, especially for special occasions.
Think about the duration you want — 2 hours is enough for a quick but memorable trip, while 3-8 hours allow for a full day of relaxation. Also, check the reviews for insights on the captain’s knowledge and the quality of the boat. Book early, especially during peak seasons, to ensure availability.
Final Thoughts
Chicago offers a surprising range of sailing adventures that appeal to different tastes and budgets. For an intimate, customizable experience, the private sailboat from Navy Pier is hard to beat. If you want to splurge on luxury with plenty of space, the catamaran is a fantastic option. And for a long, flexible day on the water, the private yacht provides all the amenities and privacy you could want.
No matter which you choose, you’ll enjoy a fresh perspective on this vibrant city. With the skyline as your backdrop, these sailing trips are good enough to make anyone fall in love with Chicago all over again. Remember to book ahead, and don’t hesitate to ask about special requests to make your trip truly memorable.