Affordable Sailing at Two Locations


  • Guaranteed Sailing
  • Flexible Scheduling
  • New Model Yachts


  • Monthly Revenue
  • Professional Yacht Management
  • Sail Your Boat 14 Times/Month

Sailing School

  • Learn to Sail Safely
  • Logically Sequenced Curriculum
  • ASA Certifications

Fleet Rates

  • Modern Design Sailboats
  • Luxurious and Comfortable
  • Efficient and Easy to Sail

SailTime Membership

Sail All Season Long For an Easy Monthly Fee

Please use the tabs at the top of the page to learn more about SailTime Chicago, and be sure to visit our fleet page. Fill out the Request Information page and to find out why SailTime Chicago is the smart and easy way to sail Lake Michigan

World-Class Training

SailTime is an ASA Awarded Sailing School

Here at SailTime Chicago, we want to help you grow as a boater.  We employ experienced instructors that will guide you through the ASA certification levels.  Become a member and enjoy access to a luxury yacht just as a boat owner would, without the usual expenses and long-term commitment.  Or purchase a boat of your own the intelligent way; through our Managed Ownership program. Whatever your experience or goals, we will help you enjoy boating on Lake Michigan.

Boat Charters

Entertain your clients, friends, and vendors

Looking for a different way to entertain clients and business associates? Forget the golf course, sailing is the best way to make an impression; they’ll always remember their first time sailing along the Chicago lakefront.  And sailing gives you plenty of time to talk over deals and connect.

Beyond entertaining, SailTime is perfect for team-building activities, rewarding high performing employees, and taking your family out for some needed off time.   You’ll spend all summer enjoying your membership boat however you want.

Sailtime chicago logo

News & Updates

Read the latest news and updates from SailTime. Check out articles, insights, care and maintenance tips, and more. For even more content and information, click the link below.

Adventure Awaits

Sail It Like You Own It!
Get more info now to learn about joining SailTime in your local area. You are on the right track to an Easy, Affordable and Smart way of getting on the water!