Take a Stand Up Paddle lesson from Chicago's top instructors.

Our entire staff are SUP safety certified through the World Paddle Association and all maintain First Aid & CPR certifications. You will not find more qualified SUP instruction any where else in Chicago. Lessons are offered in a private or group setting.


We're the only SUP company in metro Chicago to have all our instructors SUP safety certified.

One hour lessons include:

  • YOLO Board, paddle & leash
  • P.F.D. (personal flotation device)
  • On land paddle and water safety instruction
  • On water paddle instruction with a certified instructor

Intro to SUP Group Lesson

If you have ever wanted to try stand up paddle boarding now is your chance! We are offering a basic class for those new to SUP. This group class demonstrates the proper use of the board and paddle, introduces you to basic paddle techniques, stopping, turning, and has you standing and moving around on the board in no time. You need no previous experience, but should know how to swim and the class is open to all fitness levels.

Cost $45/hr each

If you've already taken our beginner lesson or you're a more experienced paddler, check out one of our SUP Group Fitness Classes or a SUP Social Paddle.

Private Lesson 1-2 People

Looking to improve your paddle stroke or increase overall strength? Take a SUP Lesson in a private setting with a knowledgeable certified instructor. Private lessons can be customized to meet the needs of the individuals from beginners to more experienced paddlers.

$75/hr each person for 1-2 people

Contact Us to make an appointment for a private lesson for you or your group. Private Group lessons are available for parties of 3+. 


Adventure awaits. Get on board this summer with a Stand Up Paddle Board rental. SUP rentals are available at Kathy Osterman 'Hollywood' Beach in Edgewater. Don't miss the chance to paddle Lake Michigan from Chicago's most beautiful beach and see the skyline like you never have before. 


  • YOLO Board, paddle & leash
  • P.F.D. (personal flotation device)
  • Basic paddle and water safety instruction

Cost $35/hour per person

Save now with a 5 or 10 visit pass

(Passes can be used for rentals, group fitness classes, and social paddles.)

Rental Quick Tips

  • Discounts available for private groups of 8+
  • Lessons are suggested but not required

  • Rentals are on a first come first serve basis
  • One hour, one person, one board





Two people Stand Up Paddle for the price of One Hour Rental 

SUP Happy Hour
Half price board rentals Fridays from 4-7 p.m.  Last renters on the water at 6:00 p.m. 


Let your SUP take you places. We offer one, two and three day SUP rentals to take off-site. Off-site rentals include a YOLO Inflatable Board, 3-piece paddle, PFD, and a leash. Pickup at Kathy Osterman Beach. 


  • 1 Day $85
  • 2 Day $140
  • 3 Day $165

Take your workouts to the water. We offer classes that combine the fastest growing sport in the world, Stand Up Paddling, with a variety of group fitness classes that will strengthen, tone and inspire you to get on the water. Designed for all levels of fitness and physical skills, our programs offer a unique and fun way to improve your overall health and well-being. SUP group fitness classes include:

  • YOLO Board, paddle, and leash
  • P.F.D. (personal flotation device)
  • Basic paddle and water safety instruction

Our SUP group fitness classes are not meant to be instructional. We highly recommend a SUP Lesson prior to taking one of these 75 minute classes.

Cost $40/each

Our SUP Group fitness CLASSES


S.U.P. Pilates

S.U.P. Pilates offers total body conditioning and balance training on the water. Using your board as a Pilates 'mat', you will experience leg strengthening, upper body toning, and core conditioning exercises that alternate with brisk bursts of paddling.



Yoga practice brings balance and restores all bodily systems by creating physical, mental and spiritual harmony. Both yoga and stand up paddle boarding are great for building better balance, coordination, endurance, and body strength.



In this class, our Fitness Onboard® certified instructors use resistance bands attached to the boards for our workouts on the water. This class is truly a full-body workout that focuses on core activation, stabilization and core endurance.


Beach Yoga + SUP 

Love yoga & the water? We have the perfect combo for you this summer! This class is divided in two: first we'll do yoga on the beach, then we'll go out as a group for a social paddle. No yoga or paddling experience necessary.

Beach Bootcamp + SUP 

Enjoy best of Chicago summer lakefront while getting your workout on with Fitness Instructor Kat Farrell. This total body workout combines 30 minutes of a beach H.I.I.T. cardio and strength workout followed by a group paddle. This land & sea class will get you in shape while having fun!


Changes to class format: Stand Up Paddling is a weather related activity. We do our best to get you out on the water for your scheduled class. In the event we are able to paddle, but are unable to do the workout on the water due to wind and water conditions, we reserve the right to make last minute changes to the format of the class from a water workout to be a beach workout (beach yoga, beach bootcamp, mat Pilates), plus a stand up paddle class.

The more the merrier. SUP Social Paddles are a great option for those who have graduated from lessons but want to keep paddling on a regular basis while enjoying the group experience. All our social paddles are led by certified instructors and we ensure you will have an enjoyable 75 minute paddle!

Cost $40 / each (includes gear rental)

Save now with a 5 or 10 visit pass.

(Passes may be used for rentals, group fitness classes, and social paddles. Passes may not be used for special events.)

Our Social Paddles

Friday: Rise & grind

Nothing is more serene than an early morning paddle to watch the sunrise over Lake Michigan. This social paddle is for our early risers who want to start the weekend off right. Enjoy a coffee back at the beach.  Friday mornings Kathy Osterman Beach. 


Wednesday: Board Meeting

New for Summer 2017! Nothing reduces workday stress like a post-work day paddle. Join us every Wednesday night for a group sunset social and unwind after a day in the office. 

Monday: Chicks with sticks

Monday nights are Ladies Night at Chicago Paddle Company. Join us for this women only social paddle. Be there or be talked about. Monday nights at Kathy Osterman Beach. 

Private Groups

It's your party. SUP if you want to. Stand up paddle boarding can make your birthday party, corporate team building, sports team cross training, or family vacation a lot more fun, active, and healthy! Whether you want a beginner lesson, a private S.U.P. Yoga or Fitness class, we can customize your package to fit your needs!

Contact us for custom pricing and to schedule your next group outing or party!

Corporate Wellness on Water 

Corporate Wellness on Water. We make it easy for your employees to be active, healthy and more productive through our Corporate Wellness on Water program.  Your employee will learn Stand Up Paddling and its health benefits, gain more skills to create ease and flow into their daily work life, and learn today's must know facts about water to improve their overall health. 

Join us for a 90-minute Corporate Wellness program that includes:

  • Stand Up Paddling (SUP)
  • Stretching to increase flexibility
  • Learning tools for managing stress
  • Reflecting on well-being and personal growth
  • Acquiring new nutritional knowledge and tricks to feel refreshed

Cost $50/each

Designed for 10-20 participants

Corporate Wellness on Water programs are led by Yoga Instructor Alison Rootberg.

Contact us to plan your corporate wellness event!