Best Charter Boats in Chicago

With nearly three decades of service to the Chicagoland area, Adventure Sea Tours, Inc., offers full-service yacht cruises for private celebrations. The company specializes in hosting events that can include wedding cruises, birthday celebrations, family events, or corporate entertainment cruises. It can accommodate as few as 30 guests or as many as 149 for three to five hours on the water. Guests enjoy views of the Chicago skyline while the celebration is ongoing.

Anita Dee Yacht Charters has specialized in customized “private and exclusive” yacht charter services for over 30 years. 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 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 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. They provide private sailing, semi-private sails are also available and power boat rentals.

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.

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.

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.

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.

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.

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.

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.