Chicago’s stunning skyline, lively lakefront, and iconic Navy Pier make it one of the best cities in the U.S. for sailing. Whether you’re after a private escape with breathtaking views or a luxurious yacht experience, Chicago offers options that cater to different preferences and budgets.
We particularly love the Private Sailing on Lake Michigan for its personalized approach and intimate setting, ideal for small groups wanting a quiet, customized adventure.
Meanwhile, the Chicago Private Catamaran stands out for its size and luxury, perfect for larger groups seeking a more upscale outing, and the Private Rental Yacht offers total flexibility for special events or leisurely exploration.
All these options let you enjoy Chicago from the water, with some of the best skyline views in the country. If you’re looking for a memorable day on Lake Michigan, this guide will help you find the perfect sailing experience.
Quick Overview
This list features three top Chicago sailing experiences, each with its unique appeal:
- The Private Sailing on Lake Michigan offers a 2-hour, fully customizable trip with a captain, perfect for small groups (Learn more).
- The Chicago Private Catamaran provides a luxurious, larger-scale sailing adventure with amenities for up to 12 people, including sunset cruises (Check details).
- The Chicago Private Rental Yacht gives you full control over your schedule and route, making it ideal for special celebrations or leisurely days (See options).
Below, we break down each tour to help you find the best fit.
1. Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago
At number one on our list, the Private Sailing on Lake Michigan provides an intimate, personalized experience with a 2-hour trip starting from Navy Pier. For around $566, your group (up to six people) gets exclusive use of a sailboat, with a captain guiding the way.
What makes this tour stand out is its fully customizable itinerary, allowing you to focus on what interests you most—whether that’s snapping photos of the skyline, cruising past Navy Pier, or even taking the helm yourself if you’re feeling adventurous.
The boat is equipped with Bluetooth speakers, so you can bring your playlist and set your vibe. Reviewers consistently praise Captain Mike for his knowledge and friendly manner, with many mentioning how flying past landmarks like the Adler Planetarium and the Chicago skyline made their trip unforgettable. The intimate size ensures you’re not crowded, and the flexibility in start times helps fit this into most schedules.
This experience is best for small groups wanting a quiet, private outing tailored precisely to their interests. It’s perfect for celebrating a special occasion or simply enjoying a peaceful day on Lake Michigan with close friends or family.
Bottom Line: If you want a relaxed, personalized sailing experience with spectacular views and a knowledgeable captain, this is your best choice.
2. Chicago: Private Catamaran Sailing for up to 12 people
Next up, the Private Catamaran Sailing offers a larger, more luxurious outing, accommodating up to 12 people comfortably. Starting at $1,500 for groups up to 13, this tour runs between 2 and 4 hours, giving you ample time to soak in Chicago’s skyline from the deck of Chicago’s largest chartered catamaran.
The boat features plush amenities designed to pamper you—think spacious seating, shade, and options for swimming or relaxing onboard.
What truly sets this experience apart is the blend of adventure and luxury. The boat’s size ensures stability, making it an ideal option for groups seeking a smooth ride and plenty of space. Sunset cruises are particularly popular, offering a tranquil setting as the city lights begin to twinkle and the skyline glows against the evening sky.
Reviews aren’t available, but the sheer size and luxury amenities suggest this is an ideal choice for larger groups, corporate parties, or families wanting a more upscale, social experience. The flexibility in duration means you can tailor your day, whether you want a quick sunset sail or a longer cruise with swimming.
Bottom Line: For groups craving a spacious, elegant sailing experience with scenic views and onboard comfort, this catamaran tops the list.
3. Chicago Private Rental Yacht Charter
Finally, the Private Rental Yacht gives you the freedom to design your own itinerary with a minimum rental of three hours. Priced at $700 for groups up to 12, this experience is less about a fixed route and more about creating your perfect day on the water.
S. Silvera Charters provides a luxury yacht where you can explore Lake Michigan at your pace, with the captain’s fees separate to keep the experience flexible.
This option is suited for those celebrating special occasions, like birthdays or anniversaries, or just travelers who want complete control over their day. The boat’s luxurious features, combined with the ability to choose your departure time and route, make it a versatile choice.
Whether you want to cruise past the city skyline, anchor for swimming, or enjoy a sunset, this charter adapts to your desires.
Reviews aren’t available, but the focus on personalization and flexible scheduling makes it attractive for those looking for exclusivity and customization. Keep in mind, the minimum three-hour rental ensures you’ll have plenty of time for relaxed exploration.
Bottom Line: If you prefer complete control and tailored experiences for a special event or leisurely cruise, this yacht charter is your best bet.
How to Choose
When deciding between these Chicago sailing options, consider your group size, budget, and what kind of experience you’re after. For small groups wanting a quiet, personalized adventure, the Private Sailing on Lake Michigan offers a great value with its intimate setting.
Larger groups or those seeking luxury and amenities might find the Private Catamaran more suitable, especially for sunset or extended cruises. If you want the freedom to customize your day entirely, the Private Rental Yacht provides maximum flexibility.
Think about your schedule too: the half-day or longer options are perfect for a relaxed pace, while shorter trips work well for quick escapes. Remember to book early, especially during peak summer months, as these experiences tend to fill up fast.
In summary, Chicago’s waterfront offers a variety of sailing experiences that suit many preferences, from private, quiet outings to luxurious group cruises. Whether you’re after an intimate ride along Navy Pier or a grand yacht adventure, you’re sure to find a boat that will make your visit even more memorable.
The key is to match your choice to your group’s size, interests, and budget—then set sail for a true Chicago adventure.