1. Lake Skyline Paddle: The Chicago skyline is sure to take your breath away during this two-hour kayak tour of Lake Michigan. With some help from seasoned guides, kayakers of all experience levels will learn the rules of the water, along with some stellar paddling techniques. Participants will glide their way along the lake, enjoying sites like North Avenue and Oak Street Beach. Through Sept. 30, tickets $100, North Avenue Beach
2. RED JAC Bicycle Ride: Seeking adventure? Take a wild ride with RED JAC on their 55-mile weekend biking event. Cruise along the Illinois countryside from Elgin to Rochelle with fellow adrenaline junkies who, like their group namesake, live to “Ride, eat, drink, jam and camp.” Cross the finish line into a skydiving jump zone that transforms into an overnight camp complete with food, beverages and live music—now that's a wheelie good time. Sept.16, 8AM, tickets from $60, 150 Dexter Ct., Elgin
3. Girls’ Back to School Meditation: Tell back-to-school stress to chill out at this one-hour meditation session at the River North Chill studio. Bring your daughter along to not only relax, but also learn helpful strategies focused on self-esteem building and tackling adolescent stress. Instructor Rhonda Duffaut will lead the workshop on all things female empowerment. Sept. 16, 9AM, adult tickets $35, 222 W. Kinzie St.
4. Chicago Half Marathon and 5K: Race to the finish line at the 21st annual Chicago half-marathon and 5K. Starting at Jackson Park, thousands of participants will run on the traffic-free Lake Shore Drive with views of the Chicago skyline to guide them to the iconic Statue of the Republic. If the 13.1 mile course doesn't sound too appealing, the LifeTime 5K kicks off at 7:30AM. Sept. 24, 7AM, tickets from $125, 6401 S. Stony Island Ave.
5. Historic Berwyn’s Bungalow Tour: Grab your walking shoes for this day-long event. Appreciate classic bungalow architecture at the Berwyn Historical Society’s 11th annual tour which takes participants inside these well-preserved homes. Take a stroll through the neighborhood while gaining rich knowledge of its residents and putting those calf muscles to work. All proceeds will go toward protecting and maintaining architectural resources in Berwyn. Sept. 24, tickets from $20, 1401 Grove Ave., Berwyn