Skate Chicago 2016

Friday, June 10 to Sunday, June 12

Back by popular demand!!! Chicago welcomes both inline and roller skaters for a free and exciting three day weekend of social street skating. We’ll take to the streets to explore the Windy City and all it has to offer. Enjoy our World Class Architecture while rolling down the streets in the loop, take in the fresh summer air while gliding along the breathtaking lakefront trail. We’ll explore city landmarks, parks, beaches, riverfront and the nightlife!      

This is a social skating event and not a competition. Skateboarders and cyclists are most welcome to join ! Helmets are required by all, and wrist guards and knee/elbow pads are also strongly recommended. Everyone will be required to sign a waiver form.
Let’s make this a weekend to remember and kick start a new tradition in 2016!


Host Hotel

Hotel Info & Book

For any questions or comments, send an email to

Rules and things to keep in mind

  • You are skating at your own risk
  • Helmets are required, all other protective gear recommended
  • You must obey all traffic laws
  • Bring your own WATER and snacks
  • Do not pass the skate leader
  • All skaters must sign the waiver
  • Have fun!
  • Friday June/10/2016

    3 PM - 6 PM

    Registration at host hotel lobby The Congress Plaza Hotel. Everyone must register and sign the waiver.

    7:00 PM - 11:00 PM

    Friday Night Skate (10-12 miles)
    Highlights: Skate to north side of Chicago. Sears tower, Art institute, Wrigley field, The second city and Lake shore trail.

    Group up at Daley Plaza skate ends at Daley Plaza

    Saturday June/11/2016

    9:30 AM - 3:30 PM

    Saturday Skate (24 miles & 16 miles)
    There are two separate Saturday skates that start at the same location and time. The longer skate is 24 miles and the shorter skate is 16 miles, and the skates will separate after 2 miles.

    24 mile skate Highlights: Skate to south and west side of Chicago. Barack Obama House, South lakefront trail, Promontory Point, Museum of Science and Industry, University of Chicago & United Center.

    16 mile skate Highlights: China town, River north, Rush & Division st, Old town, The second city, Lincoln park, Wicker park and Randolph st.

    Group up at Daley Plaza skate ends at Daley Plaza

    8:30 PM to 11:00 PM

    Group party at Emporium Arcade Bar Wicker Park
    Note that Emporium does not have food but you can bring your food to the bar. There are tons of good restaurants around the bar in Wicker Park.

    Sunday June/12/2016

    9 AM - 9:30 AM

    Dynamic Stretching and Warm-up with Kirsten (Certified Personal Trainer and Posture Alignment Specialist) at Daley Plaza (Bring shoes)

    10 AM - 1 PM

    Sunday Morning Skate. Best of Road Rave (10-12 mile)
    Highlights: The best route of Windy City Skater's signature Biweekly "Road Rave." McCormick Place, Soldier Field, Adler Planetarium, Maggie Daley Park & River walk.

    Group up at Daley Plaza skate ends at Daley Plaza