Chicago’s sailing experiences offer the best views of the city, period.
Lake Michigan’s waters provide two standout options: private charters and scheduled tours. Our favorite is the private charter experience – you’ll get a certified Coast Guard captain, freedom to swim, and your own music choice, making it perfect for small groups.
The historic Windy schooner’s 75-minute tour is another winner, featuring expert narration about the skyline’s architecture.
For a more cozy option, architectural river cruises on vintage yachts show off the city’s famous buildings from a unique angle.
Let’s explore Chicago’s top sailing tours.
Key Points
- Private Lake Michigan sailing charters offer an unforgettable experience with a licensed captain, catering to groups of up to 6 people.
- Tall Ship Windy provides 75-minute architecture and skyline sailing tours with live guides narrating about Chicago’s buildings.
- The Chicago River Architecture Tour aboard a historic yacht showcases the city’s architectural wonders in an intimate 90-minute excursion.
- Come Sailing offers private charters along the Chicago skyline with a professional U.S. Coast Guard licensed captain.
- Sailing experiences in Chicago range from private charters to public tours, providing various options for sightseeing and enjoying the city’s waterfront.
Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
This private Lake Michigan sailing charter and sightseeing tour of Chicago offers an unforgettable experience on the open waters.
With a licensed US Coast Guard captain, you’ll enjoy unparalleled views of the city skyline from the comfort of a sailboat. The tour caters to groups of up to 6 people, making it an ideal activity for special occasions or family outings.
Throughout the charter, you’ll have access to Bluetooth speakers to create a personalized soundtrack for your journey. Feel free to bring your own food and reasonable amounts of alcohol, but be mindful of any spills.
Swimming is permitted on charters of 3 hours or longer, subject to the captain’s discretion.
The tour departs and returns to the East Monroe Street & South Lake Shore Drive meeting point, ensuring a seamless experience.
With 100% traveler recommendation and an average rating of 5.0, this sailing charter promises an unforgettable adventure in the heart of Chicago.
Read our full review: Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago Review
Book now: Check availability
Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour
Explore Chicago’s iconic architecture and skyline from the decks of the majestic Tall Ship Windy. This 148-foot traditional schooner offers breathtaking 75-minute sailing tours along Lake Michigan, with options for either an Architecture and Skyline Sail or a Sunset and Skyline Sail.
Led by a live guide, the tour provides in-depth narration about the plans, people, and persistence behind Chicago’s renowned buildings. Enjoy panoramic views of the city’s stunning skyline and soak in the sunset as you sail.
Food and drinks are available from the onboard bar, and the experience is suitable for all ages.
Priced from $49.99 per person, the Tall Ship Windy tour is a flexible and affordable way to explore Chicago from the water. Reserve your spot online and enjoy free cancellation up to 24 hours in advance.
With an overall rating of 4.6/5 and high praise for the transportation and value, this sailing adventure is a must-do for visitors and locals alike.
Read our full review: Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour Review
Book now: Check availability
Chicago River Architecture Tour Aboard a Historic Yacht
Enjoy Chicago’s architectural wonders aboard a historic yacht on the Chicago River Architecture Tour. This 90-minute excursion offers a unique perspective on the city’s iconic buildings and bridges.
With a maximum of 60 travelers, you’ll enjoy an intimate experience with knowledgeable and articulate guides who provide in-depth information about Chicago’s rich history and renowned architecture.
The small boat experience allows for excellent visibility and interaction with the guide, who’ll captivate you with their expertise. Sip complimentary soda, bottled water, Starbucks coffee, and snacks as you take in the stunning views. For an additional cost, you can also indulge in beer, wine, champagne, and cocktails.
The tour is accessible, with wheelchair and stroller access, as well as accommodations for service animals. Located near public transportation, it’s easy to get to the meeting point at 465 N McClurg Ct.
While the narration may be fast-paced, the positive reviews highlight the crew’s friendliness and the guide’s exceptional knowledge, making this a must-do activity for architecture and history enthusiasts.
Read our full review: Chicago River Architecture Tour Aboard a Historic Yacht Review
Book now: Check availability
Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
Set out on a private Lake Michigan sailing charter and sightseeing cruise along the stunning Chicago skyline with Come Sailing
You’ll enjoy a 5-star experience with a professional U.S. Coast Guard licensed captain. The charter includes Bluetooth speakers, all applicable taxes, gratuities, and food and drinks. Depart from and return to the company’s location at 400 E Monroe St, Chicago.
For safety, no smoking, weapons, animals, or swimming are allowed. Glass containers are prohibited, but wine and champagne may be brought in secure containers.
Inappropriate behavior could lead to early termination without a refund. Face masks are optional, and social distancing is at your discretion. Cleaning up spills and taking garbage with you is required, and late arrivals may shorten your charter.
The captain can cancel for weather, mechanical issues, or safety concerns, but rescheduling is available. Most travelers can participate, though the charter isn’t wheelchair accessible.
Read our full review: Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise Review
Book now: Check availability
Recap
You’ll enjoy the best sailing experiences in Chicago with private charters and sightseeing tours. From Lake Michigan to the Chicago River, you’ll see the city’s iconic architecture and skyline from the water. Whether it’s a tall ship, historic yacht, or private sailboat, these tours offer unique perspectives of Chicago’s stunning natural and urban landscapes.