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
  • M-Class Learners Permit (additional information available at DMV / ilsos.gov)
  • Your valid IL Driver’s License
  • 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
Monday, Thursday, Friday in Palatine, IL
Tuesday, Wednesday, Thursday in Countryside, 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 for details.

Cancelation and Rescheduling:

14 or more days notice:

You must provide written 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. 

You may Reschedule at no additional cost for a class offered in September or October of the same calendar year.

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

If you do not show up for the first night of your scheduled course or any other scheduled day, 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 by the Riding Academy Rider Coach and the course fee will not be refunded.

Riding a motorcycle can be dangerous. If you are performing poorly and endanger yourself or other students, 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. 

WINDY CITY MOTORCYCLE SCHOOL will offer you, for one time only, the opportunity to take another course at the additional cost of $125 during the same calendar year. Please note that you have to start a new course from the beginning.

If you are late on any day of your scheduled course and miss any unit or exercise you will be considered withdrawn and the course fee will not be refunded. According to MSF Guidelines, a student enrolled in a Motorcycle Safety Class must attend all classroom units and must participate in all range exercises in order to successfully complete the course.

If you do NOT successfully complete the range portion of the course, but have successfully completed the classroom portion, you may re-enroll for the range-only portion of a class (subject to availability) for $75.

In the Classroom you will be provided:

  • All written material needed for the class including:
    • MSF® Handbooks
    • 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 the classroom sessions on Thursday and Friday evenings.