Chicago’s leading Stand Up Paddling (SUP) destination.

Join Chicago Paddle Co. in experiencing one of the fastest growing sports in the world!  Whether you are new to stand up paddling or are an experienced paddler, Chicago Paddle Co. provides you the opportunity to experience all that stand up paddle boarding has to offer—from family recreation to fitness and race training.

Stand up paddling provides some of the best fun and adventure you can have on the water! With roots in Hawaii, stand up paddling entails balancing atop a large surf-like board while propelling across a body of water with a single paddle. Due to its versatility and ease of learning, stand up paddling is exploding across the nation, and has become the most popular way for people of all ages to explore various waterways from rivers to oceans.

Chicago Paddle Co. is located at Kathy Osterman Beach—a.k.a Hollywood Beach—right on the Lake Michigan lakefront in Chicago, IL. We offer you the ability to experience stand up paddling on the most beautiful beach in Chicago, with amazing city skyline views on one side, and a gorgeous open lake on the other!

Take a beginner lesson today to get your stand up paddle experience started.

Every one of us at Chicago Paddle Co. has a passion for stand up paddling (SUP)! Our desire is to share that passion for stand up paddling with our community, and to increase community awareness of the sport. Our instructors hold certifications from the World Paddle Association and are Adult and Pediatric First Aid, CPR and AED Certified. Our instructors are the most experienced SUP staff in Chicago. We and look forward to meeting you! 


Originally from Green Bay Wisconsin, Westy has returned to his Midwest roots after several years in Florida (where he was first introduced to stand up paddling). Prior to launching Chicago Paddle Co., Westy worked for several years as a professional boat captain in the Florida Keys.

Westy is an elite team rider for YOLO Board, and is also an avid outrigger canoe paddler. He now calls Chicago "home", and has brought his love of paddling to life here in the City by launching Chicago Paddle Co. 

Westy is a World Paddle Association (WPA) Level 2 certified instructor, and is Adult and Pediatric First Aid, CPR and AED Certified.

In the off-season, Westy enjoys traveling the country teaching Advanced Paddle Technique Clinics and competing in stand up paddling races as a YOLO Board team rider.

Listen for Westy on Stoke Radio, the only radio station dedicated to paddlers.


Originally from Kansas, Amy has been a Chicago native for fifteen years. As an avid runner and accomplished triathlete, Amy has always enjoyed the beautiful Chicago lakefront. As an owner and co-founder of Chicago Paddle Co. Amy is devoted to sharing her love of paddling with other Chicagoans!

Amy is a PaddleFit Level 2 and World Paddle Association (WPA) Level 1 certified instructor, and is Adult and Pediatric First Aid, CPR and AED Certified. She is also a brand ambassador for Lole Women. 

maximize your paddle experience

YOLO Boards

We proudly use YOLO Board for our full paddle board fleet. YOLO Board is best known both for their top quality paddle boards and for their lifestyle mantra ‘You Only Live Once’. We provide both recreational boards as well as performance race boards.

Contact us regarding board sales

KIALOA Paddles

We use Kialoa paddles to enhance our customer’s overall Stand Up Paddling experience. Kialoa is known for building the best paddles in the world; they produce a full line of stand up, outrigger and dragon boat paddles. Kialoa’s mission statement, "At Kialoa we live like we paddle," is built on three guiding principles: PO’OKELA (Excellence), MALAMA (Stewardship), and LAULIMA (Teamwork), making them a perfect partner for Chicago Paddle Co.

Contact us regarding paddle sales

Gear storage

We are happy to store your board and paddle for the season with one of our SUP Gear Storage packages.