Chicago Sailing with a Sailo Boat Charter

Renting a boat charter in Chicago is one of the best things to do in the summer months, whether you’re planning to party or just to escape the city heat. Find your perfect private boat rental with Sailo!

Despite being a long way from the sea, Chicago offers lots of things to do out on the water. From helming a sailboat, going on a fishing trip or enjoying the wild parties of the summer months, there is always something going on. When it comes to choosing your ideal yacht, Sailo offer the perfect selection of boat charters in Chicago for adventure boat trips, bachelor or bachelorette parties, or big events like weddings or corporate meetings.

Sailing the Windy City

Feeling the wind in the sails of your Chicago boat charter out on Lake Michigan is one of the best ways to take in the awe inspiring views of the Windy City. The lake makes a great playground, especially in the summer months, with plenty of coastline to explore. 

Just a short boat ride from downtown Chicago there is a whole world of fishing towns and beaches. Sure, you could drive there, but the adventure and thrill of sailing is something special which can really make a big difference to your vacation. Most people rent a yacht charter from Chicago for a day trip, but there is always the option for something longer if you would like to explore.

Partying in Chi-Town

Chicago likes to party, and one of the most wild parties is the Chicago Scene Boat Party. Hundreds of boats and thousands of attendees arrive at the Playpen, an area just off the shore of the downtown area. People from all walks of life come to enjoy a day on the deck of their yacht and party like there's no tomorrow.

All year round, of course, there are also plenty of opportunities to party on the water. You’ll find Sailo offers a great selection of party boats in Chicago which are perfect for big or small groups. Whatever the occasion, from weddings or corporate events to a wild weekend of partying, take a look at our selection of great motor yachts and sailboats on the shores of Lake Michigan.