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 or our new location in downtown Highland Park. Everything you see online is also available in-store at one of our two locations and our expert staff is here for personalized advice.

Learn Something

the latest inlearn something

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Best Downhill Longboards 2016

If you've got a need for speed then your next downhill longboard is definitely on this list. We break down the best downhill longboards for summer 2016.

Best Cruiser Longboards 2016

A good cruiser board is like a best friend that you can stash in your locker. We made a list of our favorite cruiser boards for summer 2016 so you can find your next "best friend".

Best Carving Longboards 2016

The results are in - we've got a list of the industries best carving longboards for summer 2016!

Loaded Longboard Review 2016

Doing it better than so many brands, since 2000, Loaded has perfect the art of longboard technology. We break down what makes them the best and which boards are our personal favorites.

WW

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02 oct 2016

The Fourth Phase Snowboard Movie Premiere

Join us for The Fourth Phase global movie premiere on Oct 2nd, 7pm CT at Windward Boardshop Chicago.

7 oct 2016

Windward Highland Park Ladies Shopping Night and Jewelry Trunk Show

Join us from 6-8pm for complimentary drinks, snacks, a first look at our winter 2017 collection and of course direct access to Erin's beautiful handmade jewelry

16 sep 2016

Chill Chicago Golf Scramble

Join Windward and our good friends at the Chicago Chill Foundation for the first annual Chill Chicago Golf Scramble!

27 jul 2016

Windward x Brooklyn Cloth x Chill Foundation Pop Up Shop Party

Join Windward, Brooklyn Cloth and the Chicago Chill Foundation for a one-night-only pop up shop party and a chance to win 2 x 4-day passes to Lollapalooza!