Lake Michigan’s sailing scene delivers Chicago’s most impressive views and experiences. A private charter cruise gives you freedom to explore the lake while admiring the city’s famous skyline – perfect for photographers and architecture buffs.
We love the historic Tall Ship Windy’s sunset tours for their combination of sailing heritage and dramatic evening views. For small groups, the 13-passenger catamarans offer intimate, memorable outings with plenty of space to move around.
These vessels and their experienced crews make Chicago’s sailing tours worth every penny. Let’s check out the best sailing options available.
Key Points
- Come Sailing offers a highly-recommended private Lake Michigan sailing charter for up to 6 people at $483.96 per group.
- The 148-foot Tall Ship Windy provides a 75-minute architecture and skyline sailing tour starting from €47.18 per person.
- The “Latitude Adjustment” catamaran accommodates up to 13 people for a 2-4 hour private cruise, priced from €1,415.61 per group.
- Private yacht charters in Chicago start from $1,600 for a 2-hour experience, offering customizable experiences and panoramic skyline views.
- The Chicago Skyline Cruise, led by a US Coast Guard-licensed captain, provides breathtaking views of the iconic architecture with optional amenities.
Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
A private Lake Michigan sailing charter and sightseeing tour in Chicago provides an unparalleled opportunity to experience the city’s stunning skyline and lakefront from the water.
Operated by Come Sailing, this highly-rated tour boasts 60 reviews with a 100% recommendation rate from travelers. Priced at $483.96 per group (up to 6), the charter offers free cancellation up to 24 hours in advance and confirmation upon booking.
The tour departs from the northeast corner of Lake Shore Dr. and Monroe St., with the boat meeting guests along the Monroe Harbor wall. Passengers should follow the lakefront trail north to the harbor’s edge.
The charter has a few regulations, including no smoking, no weapons or animals, and limited alcohol use in plastic cups. Swimming may be permitted on longer charters, with a waiver required.
COVID-19 precautions include optional face masks and social distancing. Customers consistently praise the knowledgeable captains, clean boat, and stunning city views, making this an unforgettable Chicago experience.
Read our full review: Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago Review
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Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
The Come Sailing private Lake Michigan sailing charter and sightseeing cruise offers an unparalleled opportunity to admire Chicago’s stunning skyline from the tranquil waters.
With a 5.0 overall rating based on 4 reviews, this US Coast Guard-licensed captain-led experience provides guests with Bluetooth speakers and breathtaking views of the city’s iconic architecture.
While smoking and inappropriate behavior are prohibited, guests may bring reasonable amounts of alcohol, excluding glass containers.
Health and safety guidelines, including optional mask-wearing and social distancing, are in place to ensure a comfortable journey.
Restroom access is limited, so guests are encouraged to use public facilities before boarding.
Cancellations may occur due to weather, mechanical issues, or safety concerns, but refunds are available if rescheduling isn’t possible.
Guests should also be aware that late arrivals may result in shortened charters without refund, and cleaning fees may be assessed for excessive spillage or inappropriate conduct.
Photography consent is implied upon boarding for promotional purposes.
Read our full review: Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise Review
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Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour
Set sail on the 148-foot Tall Ship Windy, Chicago’s official Tall Ship Ambassador, for a 75-minute architecture and skyline sailing tour.
With prices starting from €47.18 per person, this tour offers spectacular views of Chicago’s iconic skyline and sunset over the skyscrapers.
Choose between an architecture and history-focused tour or a sunset sail, and enjoy live onboard narration in English, providing educational insights about the city’s architecture and history.
The tour departs from the Tall Ship Windy ticket booth at Navy Pier, and weather-appropriate clothing is recommended.
Smoking isn’t allowed, and the tour isn’t suitable for wheelchair users.
With a 4.6/5 overall rating based on 44 reviews, the tour has received mixed feedback, with some customers finding it wonderful and others describing it as slow and boring.
Cancellation is free up to 24 hours in advance for a full refund, and food and drinks are available for purchase onboard.
Read our full review: Chicago: Tall Ship Windy Architecture & Skyline Sailing Tour Review
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Chicago: Private Catamaran Sailing for up to 12 People
Sailing enthusiasts can embark on a private catamaran adventure in Chicago’s picturesque Monroe Harbor. The “Latitude Adjustment,” Chicago’s largest chartered catamaran, can accommodate up to 13 people for a 2-4 hour cruise. Priced from €1,415.61 per group, this experience offers a range of amenities, including a full kitchen, grill, cooler, and Bluetooth radio, ensuring a comfortable and customizable journey.
Guests can savor stunning views of the Chicago skyline, swim, grill, and enjoy BYOB options. The vessel is equipped with luxury features for a pleasant experience.
Groups over 6 must hire a qualified operator if not skippers. The owner provides a list of pre-screened operators, with an estimated cost of $10-$11 per person per hour.
While the experience isn’t suitable for those prone to seasickness or other conditions, it presents an opportunity to create cherished memories on the waters of Lake Michigan.
Read our full review: Chicago: Private Catamaran Sailing for up to 12 People Review
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Chicago: Private Yacht Charter
Adventurous travelers can charter a private yacht in Chicago to explore the city’s stunning lakefront from the waters of Lake Michigan.
For those seeking a more exclusive and personalized experience, a private yacht charter offers the ultimate in luxury and flexibility. Prices start from $1,600 for a 2-hour charter that can accommodate up to 6 guests, with longer durations and larger group sizes available.
Guests can customize their experience, choosing from various yacht sizes, amenities, and catering options to suit their preferences. The private yachts boast comfortable seating, on-board bars, and panoramic views of the Chicago skyline.
Cruising along the shoreline, passengers can admire iconic landmarks like the Willis Tower, Navy Pier, and the Museum Campus.
Whether celebrating a special occasion or simply seeking a unique way to explore the city, a private yacht charter in Chicago promises an unforgettable experience on the water.
Read our full review: Chicago: Private Yacht Charter Review
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The Sum Up
Chicago’s waterfront offers a variety of sailing experiences, from private charters on Lake Michigan to sightseeing cruises along the iconic skyline. Visitors can choose from tall ships, catamarans, and yachts, providing the opportunity to enjoy the city’s stunning architecture and natural beauty from a unique perspective on the water.