Learn to Sail in Chicago: Two Premier Locations with SailTime’s ASA Sailing School
If you’re ready to make this the year you take the helm, SailTime Chicago is here to help you do just that. Now entering its 20th year of offering American Sailing Association (ASA) certified sailing lessons, our school proudly serves both members and the general public. Whether you’re new to sailing or working toward advanced certifications, our hands-on program gives you the skills and confidence to skipper your own sailboat safely.
Our sailing school courses are offered in two convenient locations: Burnham Harbor in downtown Chicago and Winthrop Harbor at the Illinois-Wisconsin state line.
Sail Chicago’s Iconic Waters
Chicago is home to one of the most exciting sailing scenes in the country. With stunning skyline views, dynamic harbor traffic, and direct access to Lake Michigan, it’s the perfect setting for real-world sailing experience. Whether you’re navigating the busy waters of Burnham Harbor or enjoying open-water training out of Winthrop Harbor, you’ll encounter conditions that truly prepare you for independent sailing.
A Full Range of ASA-Certified Courses
SailTime Chicago offers a complete lineup of ASA certification courses designed to guide you from beginner through advanced levels:
- ASA 101 – Basic Keelboat Sailing
- ASA 103 – Basic Coastal Cruising
- ASA 104 – Bareboat Cruising
- ASA 105 – Coastal Navigation
- ASA 106 – Advanced Coastal Cruising
- ASA 118 – Docking Endorsement (we’re one of the few Midwest schools offering this valuable course)
Whether your goal is to sail locally, charter internationally, or simply feel more confident at the helm, our structured program ensures you’ll have the skills to succeed.
All On-the-Water, Hands-On Learning
At SailTime Chicago, we believe the best way to learn to sail is by doing. That’s why our program features 100% on-the-water instruction. There’s no classroom time — just practical experience aboard modern yachts.
Here’s how it works:
- Before your first lesson, you’ll receive study materials to review at your own pace.
- When you arrive for your lesson, we get right out on the water so you can immediately begin practicing what you’ve learned.
- Our training vessels — 33- and 36-foot yachts — offer a safe, stable, and responsive platform for developing your sailing skills.
From hoisting sails to docking, from tacking to anchoring, your learn to sail time is focused entirely on building real ability and confidence to truly enjoy sailing.
Flexible Scheduling to Fit Your Life
The Chicago sailing season officially kicks off each season on May 1st, and we begin lessons right away. Classes are thoughtfully scheduled around student demand, making it easy to find a time that fits your lifestyle—weekday, evening, or weekend options are all available. Whether you’re starting fresh and want to learn to sail or you want to build on past experience, we’ll help you craft a learning path that works for you. Both private instruction and small-group formats are offered to ensure a personalized, hands-on experience on the water.
Why Learn to Sail at SailTime Chicago’s Sailing School?
- 20 years of trusted instruction — We’ve helped sailors succeed since 2005.
- Two great locations — Train downtown or near the state line at Winthrop Harbor.
- Hands-on learning — Every moment of your lesson is spent on the water.
- Small class sizes — Get personalized attention and maximum time at the helm.
- Unique ASA 118 docking training — Build skills that give you confidence in any harbor.
- Pathway to membership — When you learn to sail, our certifications open the door to SailTime yacht access without the responsibility of ownership.
Get Started on Your Sailing Journey
If you’re ready to learn to sail this season, SailTime Chicago is here to help you take the first step.
Contact us today for the latest class schedule and details. Let’s get you out on the water and on your way to becoming a confident, capable sailor!
