Laurels
Best Boat Charters
in Chicago
2017

Why These Boat Charters?

Our goal is to connect people with the best local experts. We scored boat charters on more than 25 variables across five categories, and analysed the results to give you a hand-picked list of the best boat charters in Chicago, IL.

ReviewedCuratedTop Picks71943818

Our Selection Criteria:

  • 1. Reputation

    A history of delighted customers and outstanding service.

  • 2. Credibility

    Building customer confidence with licensing, accreditations, and awards.

  • 3. Experience

    Masters of their craft, based on years of practical experience and education.

  • 4. Availability

    Consistently approachable and responsive, so customers never feel ignored.

  • 5. Professionalism

    Providing service with honesty, reliability, and respect.

Anita Dee Yacht Charters

Anita Dee Yacht Charters specializes in fully customizable events aboard their two private luxury yacht venues for residents and tourists in the Chicago metro area. Their fully equipped boats can accommodate up to 135 or 400 guests and also provide catering and entertainment. Anita Dee Yacht Charters has hosted corporate events, wedding celebrations, social and school events, and special event dates. Former customers speak highly of their friendly and accommodating staff, and catering service.

Chicago, IL(312) 379-3191

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Chicago Line Cruises

Chicago Line Cruises specializes in boat tours throughout Chicago’s historical and architectural sites for over three decades. Owner Terry Johnson and Paul McCarthy are former lawyers who purchased their first boat in 1981 and turned their small business idea into an awarding-winning company. Now they have over ten staff members and have been praised in Time Out Chicago as one of the most engaging tours in the city. Charter boat services are also available which offers a full-service bar, a professional sound system, and more. Former customers speak highly of their knowledgeable and friendly staff.

Chicago, IL(312) 527-1977

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Chicago Sailboat Charters

Chicago Sailboat Charters provides a variety of sailing experiences in the Chicago area. They offer night sailing, firework shows, historical cruises, and swimming and sunbathing sailing trips. Also, weekday daytime sailboat rentals receive a 20 to 30 percent discount. Former customers speak highly of their professionalism and accommodating staff. Private sails fit up to 6 to 10 guests, and semi-private sailing is also available.

Chicago, IL(773) 236-7245

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Chicago Sailing

Chicago Sailing is the largest adult lesson provider in the Chicago metro area for the past three decades. Experienced sailing teachers certify hundreds of students annually according to U.S. Sailing standards. Their fleet of 26 keelboats are available for hourly rentals, and customers can reserve captained charters between mid-April to October. Chicago Sailing is highly rated on Facebook where customers speak highly of their flexibility, friendliness, and professionalism.

Chicago, IL(773) 871-7245

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Chicago Yacht Works

Chicago Yacht Works is a single-source boating facility providing Chicago residents with a one-stop shop for their boating needs. This full-service boat dealer offers new, used, and rental services, boat parts, accessories, and storage. Their 10+ acres facility sits in front of 600 feet of river frontage which creates a convenient location for new and regular customers. Former and current customers speak highly of their low-cost solutions, professionalism, and accommodating staff.

Chicago, IL(312) 666-6670

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Fairwind Sail Charters

Fairwind Sail Charters is one of Chicago’s oldest American Sailing Associated schools with almost four decades of experience. Fairwind Sail Charters provides award-winning ASA sailing lessons for students at any level. They also feature a Sailing Yacht Lease Share Program where members can sail their yacht all season long at a fraction of what it costs to rent or own. Former customers speak highly of their dedication to safety, spotless boats, and patience.

Riverside, IL(708) 442-2670

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Free Spirit Yacht Cruises

Free Spirit Yacht Cruises provides private yacht charters on Lake Michigan for residents and tourists in the Chicago metro area. This family owned business offers two luxury yachts, one smaller for intimate parties, wedding proposals, and meetings, and the larger yacht which accommodates up to 120 people. Select charter cruises are also available - fireworks, air and water shows, 4th of July, and more. Former customers speak highly of their informative tours, spacious boats, and customer service.

Chicago, IL(708) 361-2220

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Island Party Boat

Island Party Boat is a charter and rental boat service for residents and tourists in the Chicago metro area. They have six tiki party themed boats which can accommodate groups of 2 to 90 people. Sailboat and Powerboat rentals are also available. Their ticketed cruises offer an up-close view of firework shows or relaxing rides down the Chicago River with a cocktail in hand. Former customers speak highly of their professionalism and friendly crew.

Chicago, IL(312) 600-8454

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Knock Out Charters

Knock Out Charters is a boat cruise and rental service in Chicago specializing in tourism and special events. Captain Chris Connor is a licensed Master Captain and has over 40 years of boating experience. Packages offered are concert tailgating, marriage proposal, sunbathing, swimming, and casino boat specials. Customers can also rent a private charter any day of the week. Former customers speak highly of their friendliness and knowledge of Chicago’s history.

Chicago, IL(773) 230-9173

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Offshore 312

Offshore 312 is a charter rental service specializes in parties and cruises for residents and tourists in the Chicago metro area. Boats can accommodate up to 12 adults and feature two bedrooms, two full bathrooms, a swimming platform, lounge area, and more. Offshore 312 also offers aquatic pub crawls, concert tailgating, playpen swim parties, sunset cruises, corporate events, and more. They currently hold a five-star rating on Yelp! where customers speak highly of their spacious boats, knowledgeable staff, and onboard amenities.

Chicago, IL(312) 767-7503

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Party on Boats

Party on Boats specializes in fully customizable events aboard one of their three private luxury yachts for residents and tourists in the Chicago metro area. Owner and captain Greg is licensed by the United States Coast Guard and has 40 years of sailing experience. Party on Boats offers breathtaking views of the Chicago skyline and architectural sightseeing from their outdoor observation decks. They currently hold a five-star rating on Yelp! where customers speak highly of their spotless boats, accommodating staff, and flexibility.

Chicago, IL(773) 417-5959

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Playin’ Hooky Charters

Playin’ Hooky Charters provides fishing charters for residents and tourists in the Chicago metro area. Captain John Wagner is licensed by the U.S. Coast Guard and has more than 30 years of fishing experience on Lake Michigan. All necessary equipment is provided and full or half day trips are available. Playin’ Hooky Charters carries all Coast Guard approved safety equipment and life preservers for ultimate security and comfort.

Morton Grove, IL(847) 313-9678

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Seabreeze Charter

Seabreeze Charter is a private sailboat chartering company specializing in sunset and firework cruises in Chicago. Captain Lorenzo is licensed by the United States Coast Guard and has over 30 years of sailing experience. Seabreeze Charter also offers classes and sailing vacation packages. They are highly reviewed and rated on Yelp! where customers speak favorably of their professionalism, customer service, and knowledge.

Chicago, IL(312) 878-7587

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Sun Sea Yacht Charters, Inc.

Sun Sea Yacht Charters, Inc. specializes in cruises on Lake Michigan and the Chicago River for tourists and residents in the Chicago metro area. Sun Sea captains have over 50 years of combined sailing experience on the Great Lakes, Mississippi River, the ocean, and the Intracoastal Waterways of Florida. Yachts feature dining areas, modern galleries, dinettes, staterooms, and full baths. Former customers speak highly of their accommodating staff, great luncheon services, and hospitality.

Chicago, IL(630) 323-5884

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Swel Sailing Chicago

Swel Sailing Chicago is a Chicago-based charter company specializing in sailing excursions for almost five years. Trained staff members strive to offer the best sailing experience by providing luxury, excitement, comfort, and relaxation. Packages available are bed and breakfast and firework specials. Former customers speak highly of Captain Bob and Lauren’s helpful, flexible, professional, and understanding approach.

Chicago, IL(847) 275-0870

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The Advantaged Chicago

The Advantaged Chicago is a charter service specializing in sightseeing tours and events for tourists and residents in the Chicago metro area for over a decade. Charters for a half day to a month are available and experienced staff member also provide assistance in buying or trading yachts. The Advantage Chicago has hosted a broad range of parties such as family gatherings, birthday parties, dinner cruises, bachelor/bachelorette cruises, weddings, and more. They currently hold a five-star rating on Yelp! where customers speak highly of their hassle-free booking, and knowledgeable and friendly staff.

Chicago, IL(312) 515-0551

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Two Brothers Sailing Adventures

Two Brothers Sailing Adventures specializes in boat charters, rentals, and sailing lessons for residents and tourists in the Chicago metro area. Captains Lynda Stephens and Jeff Harris are both U.S. Coast Guard licensed with extensive sailing experience. Packages include cityscape, sunset, off-shore, party, romance, and team building cruises. Former customers speak highly of their knowledge, sense of humor, and competitive prices.

Chicago, IL(630) 816-1427

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Vantage Yacht Club

Vantage Yacht Club is a boat rental company available for tourists and residents in the Chicago metro area with over five years of experience. Their fleet consists of 7 different boats which can accommodate up to 12 guests. Also, a Vantage Boat Club program is available where members have priority reservations at special rates without long term commitments. Former customers speak highly of their scenic tours, accommodating staff, and spotless boats.

Chicago, IL(855) 777-1855

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