H-D Riding Academy

Welcome To Chicago Motorcycle School and Milwaukee Motorcycle School!

Never ridden before? Don't Sweat it. Chicago Motorcycle School and Milwaukee Motorcycle School are designed to make you comfortable on a bike and give you the skills you need to ride with confidence.

If you live anywhere in the Chicagoland and South Wisconsin area - from Chicago's lakefront to Starved Rock - you're ready to embark on an exciting adventure into the two-wheeled world, look no further. The Harley-Davidson® Riding Academy Learn to Ride Class is Harley-Davidson®'s Academy of Motorcycling.

Combining the proven curriculum of the Motorcycle Safety Foundation® and the excitement and passion of Harley-Davidson®, the New Rider Course offers unrivaled hands-on instruction that will bring your motorcycling dreams to life and give you the skills and confidence you need to get the most out of riding.

The Course is a mixture of classroom time and actual riding that delivers the basics of motorcycle operation in Harley-Davidson® style. It's taught by experts certified by both the Motorcycle Safety Foundation® (MSF) and Harley-Davidson® to provide top notch instruction in a relaxed, fun environment. After passing a written test and a riding skills evaluation, you'll receive a MSF RiderCourse® Completion Card that may qualify you for discounts on motorcycle insurance, depending on the provider. More than that, you'll start a journey that will last a lifetime.


  • Be 18 years of age at the time of class
  • ONLINE PRE-COURSE: The MSF Basic eCourse is required to be completed before coming to class. This 3-hour online course is to be taken no more than 30 days before your class. Please log onto the MSF website to register and complete your MSF Basic e-Course. The Basic e-Course costs $19.99 and is not included in the cost of our class. You are required to bring proof of successful completion of this online course to ride in our program. eCourse registration link HERE
  • M-CLASS LEARNERS PERMIT for Illinois Students taking the course in IL (additional information available at DMV / ilsos.gov)
    • A permit is NOT required for Wisconsin Students taking the course in WI
  • Your valid Driver’s License
    • IL driver’s license for taking class in IL
    • WI driver’s license for taking class in WI
  • A DOT approved Motorcycle helmet
  • Protective Eye Wear
  • Leather Full Finger Gloves
  • Long-Sleeved Shirt or Jacket
  • Over-the-Ankle Boots
  • Jeans or Motorcycling Pants


    With classes offered throughout the Chicago & Southern Wisconsin areas.  Chicago Motorcycle School and Milwaukee Motorcycle School are the best options for anyone who wants to learn to ride a motorcycle.


    While in the Classroom and on the range you will be treated to a great learning experience. The Harley-Davidson® Motorcycle Riding Academy course is an extremely interactive and inclusive experience.


    You will be riding a 494cc Harley-Davidson® Street 500® - a responsive, mid-weight streetbike that's easy to handle and rider-friendly. But make no mistake, the Street 500 is a real-world bike that can take you as far as you want to go.

    Class Scheduling: 

    Classes are conducted over 3 or 4 days and attendance at all classes is mandatory for successful completion of the course. Be sure the class you select works with your schedule.

    Illinois Weekday Classes are Held (see schedule for specific class times)
    Monday, Wednesday, Thursday in Villa Park, IL
    Tuesday, Wednesday, Thursday in Countryside, IL & Woodstock, IL

    Illinois Weekend Classes are Held
    Thursday and Friday 5:00pm - 8:00pm
    Saturday and Sunday 8:00am - 5:00pm

    Wisconsin Weekend Classes are Held
    Thursday 5:30pm - 8:30pm
    Saturday and Sunday 8:00am - 5:00pm
    Monday 5:30pm - 8:00pm


    The Motorcycle Riding School Course costs $350 per person in Illinois and $369 per person in Wisconsin.
    Group discounts of 3 or more are available.
    Call 630.433.3490 or email Riding_Academy@windycityhd.com for details.

    Cancelation and Rescheduling:

    14 or more days notice required:

    You must provide written/email notice at least 14 days before your class start date to cancel for a full refund or to request that we reschedule you into a future class.

    Any notification less than 14 days will result in no refund and rescheduling is handled on a case-by-case basis. 

    Once a student has begun a class there will be no refund option for any reason.

    If you do not show up or arrive late for the first night of your scheduled course or any other scheduled class session, you will be considered as having withdrawn from the course and the course fee will not be refunded.

    If you leave or sit out any scheduled exercise or classroom unit for any reason, you will be considered withdrawn from the course and the course fee will not be refunded. By MSF Guidelines, a student must attend all classroom units and must participate in all range exercises in order to successfully complete the course.

    Riding a motorcycle can be dangerous. If you are performing poorly and endanger yourself or others, the instructor may review your performance and recommend that you withdraw from the course.

    You may also voluntarily withdraw from the course at any point if you do not feel comfortable enough to continue, the course fee will not be refunded.

    In the Classroom you will be provided:

    • All written material needed for the class including:
      • Harley-Davidson® Riding Academy Roadbook
    • Miscellaneous handouts and gifts from the dealerships
    • Water and coffee

    On the Range you will be provided:

    • The motorcycle you will learn on (a Harley-Davidson® Street 500® 494cc motorcycle)
    • Expert guidance and training from highly trained and qualified motorcycle instructors
    • Water
    • An experience like none you have ever had before

    Please be prepared for inclement weather

    Our classes are not canceled or postponed unless lightning, excessive rain or snow makes riding the motorcycles impossible. After all, in the real world traffic does not stop for foul weather.

    Some items you may need for the course are:

    • Extra layers (cotton is not recommended unless temperatures warrant)
    • Rain Gear
    • Extra Gloves and Socks

    Everything you may require for the course is available for purchase at the dealerships. You will have ample opportunities to make any additional purchases during your classroom sessions.