Your January 2026 Chicago Skate Guide: Learn Roller Dance from a Pro!

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Hey Chicago skaters! As the winter winds howl, our incredible skate scene isn’t hibernating—it’s just moving indoors and heating up! While our app’s discovery feed was quiet this past month, the city is buzzing with opportunities to keep your wheels spinning and skills sharp heading into the new year. The absolute must-do event is the chance to learn from the best in a Fitness Class: Roller Dance with pro skater Myesha McCaskill. It’s the perfect way to add some new moves to your arsenal for 2026.

Beyond that, there’s a ton of action to get into. If you’re craving some high-impact excitement, you can’t miss the Home Teams Triple Header with the legendary Windy City Rollers. And for those just looking for some classic rink time with friends and family, the Winter Break Fun at Dr. MLK Skating & Bowling Center offers a whole schedule of public sessions to keep you rolling through the holidays. Let’s lace up and show this winter how Chicago rolls!

Meet the Skaters of Chicago

We love seeing the Chicago skate family grow, but no new skaters introduced themselves on the app recently. Don’t be shy! Create a profile, share your skate style, and connect with the incredible crew we have here in the Windy City. Let’s see who’s rolling into the new year with us!

Get the full picture of the Chicago skate scene. Download the Let's Roll app!