Why Windward Boardshop?

Since 1982, Windward has served the boardsports, outdoor and apparel industry with top-notch recommendations and un-matched customer service. We invite you to take a look around. Feel free to contact us if we can help at all along the way. Here are some quick facts to get you started.

We Ride First

Gear Tested & Approved

We are snowboarders, stand up paddle boarders, longboarders and skateboarders. Riding the gear we sell is key in a good recommendation for you. Plus, our staff has been riding on average 15+ years and just can't stop.

Since 1982

30+ Years of Expert Knowledge & Service

Our decades of riding experience gives us the know how to get riders like you into the right gear for your next adventure. Take it from others just like you, browse our 5-star collection on Yelp & Shopper Approved.

Fast Free Shipping

No Minimum Orders To Get It

Sure, others offer free shipping that might get there in 7-10 days. Our average free delivery time is 2.5 days with over 95% of shipments arriving in 4 days or less. We can't laser beam it to you just yet but we're getting close.

365 Day Free Returns

Easy Return Label In The Box

Sometimes it just doesn't fit right or isn't exactly what you expected. No problem, as long as the item is brand new w/tags, you have a full 365 days to return it. Just look for your pre-paid free return label included with every order.

Shop Secure

128-bit encryption + No Sensitive Storage

Shop with security and peace of mind under our 128-bit encryption powered by Thawte and credit card processing with Authorize.net or PayPal. All major credit cards are accepted and we don't store your private credit card account info.

Shop Local

Everything Online Is Also In-Store

Visit us at Chicago's original boardshop, just south of Wrigley Field. Everything you see online is also available in-store and our expert staff is here for personalized advice. Short on time? Use in-store pickup at checkout for speedy results.

Learn Something

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get more knowledge & news

Riviera Paddlesurf Paddleboard Review 2015

The SUP season is upon us and Riviera Paddlesurf is back with another killer collection of boards. New colors, sizes and shapes for every type of paddler.

Best Carving Longboards 2015

With the 2015 longboards arriving, we hand-picked a list of our favorite carving longboards. Check out some of the best carving longboards for 2015.

Best Downhill Longboards 2015

The results are in, we've got a list of some of the best downhill longboards for 2015. See if your dream board made the cut!

Best Cruiser Longboards 2015

For city ripping or quick trips to the liquor store, cruiser longboards are the ideal way to get around. Here is a list of our favorites for 2015.

WW

the latest inwindward events

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21 jun 2015

Go Skate Day 2015

Celebrate skateboarding's annual holiday, Go Skateboard Day, with us at Wilson Skatepark on June 21st.

28 jun 2015

Stand Up Against Blood Cancers 2015

Paddle for charity and help fight blood cancers with the Columbia Yacht Club, Windward and the Leukemia & Lymphoma Society on June 28th, 2015.

18 jul 2015

Columbia Yacht Club SUP Cup 2015

The Inaugural Columbia Yacht Club SUP Cup is on July 18th, 2015.

26 apr 2015

The Hunt Longboard Race 2015

Chicago's Scavenger Hunt on Longboards is back for 2015.