Owl Ride for Jackson

Group of cyclists in matching jerseys riding in a city street with "Chicago" sign in the background.

August 15 & 16, 2026

The Owl Ride for Jackson is a two-day 111-mile roundtrip bike ride from Chicago to Valparaiso, IN. Taking off from Chicago’s lakefront, the route serves up breathtaking views and scenic bike trails to Valparaiso. Day 1, bikers ride 55.5 miles, enjoy a complimentary dinner and an evening in Valpo, and then on day 2, ride another 55.5 miles back to Chicago. With a mix of rolling terrain and a few punchy climbs it offers something for cyclists of all abilities. A 1-day option is available. All riders are invited to enjoy a post ride celebration on Sunday including dinner, treats, and massages!

Proceeds from Owl Ride for Jackson benefit JCF’s NICU Transportation Program which partners with Ann & Robert H. Lurie Children’s Hospital, Northwestern Prentice Women’s Hospital and Rush University Children’s Hospital to provide complimentary parking passes for families with critically ill babies in the NICU. Challenge yourself or enjoy the ride while impacting so many families when they need it most.

Register to Ride
Support a Rider or Team
Cyclists riding on a paved trail through lush green forested area, with fallen leaves on the path.

Weekend Timeline:

Saturday:

  • 5:00 AM – 5:45 AM: Check-in, Bag Drop-off, and Bike Safety Check

  • 6:00 AM: Day 1 Departure

  • 1:45 PM: Valparaiso Arrival

  • 6:30 PM: Team Chance Dinner

Sunday:

  • 6:00 AM – 6:30 AM: Check-in, Bag Drop-off, and Bike Safety Check

  • 7:00 AM: Day 2 Departure

  • 2:30 PM: Chicago Arrival and Post-Ride Celebration

GET INVOLVED

  • Training Rides start in Summer 2026 and will take place every other Sunday morning. The Sunday rides will take off from Caldwell Woods Parking Lot (Devon Ave and Milwaukee Ave) starting at 7:00am. Please be sure to bring water, any nutrition you may need, and sunscreen. Also, you must provide your own bike and HELMETS ARE MANDATORY! 

  • Sponsorships are available ranging from $1,000 - $10,000 and not only support the mission, but amazing athletes! Click here to view our Sponsorship Levels!

    If you would like to sponsor the Owl Ride, click here!

  • The Owl Ride Event Committees help ensure the success of the Owl Ride! Email us at info@jacksonchance.org to learn more about each committee responsibilities and find out which committee fits your expertise!

Learn more
Two people wearing orange shirts, holding plush owl toys, standing indoors in front of a sign with "JC" and "Jackson Chance". They appear to be at an event or promotion.
A diverse group of people, including adults and children, standing on a city sidewalk, holding signs supporting "Team Chance" with messages like "Go Riders!" and "You Did It!" Many are wearing orange shirts. The background features a brick building w
Group of people sitting at a restaurant table, smiling for a photo. The table is covered with a white tablecloth and orange runner. Drinks and napkins are on the table. The background shows a bar with shelves of bottles and a TV.
Group of four people smiling at an indoor event, two wearing "Jackson Chance Foundation" shirts, with bicycles in the background.
A group of people gathered on a city sidewalk, some wearing orange shirts and holding signs. The setting includes a brick building and trees along the street. The number "2255" is visible on the building. The mood appears to be supportive and collabo
Group of cyclists wearing helmets and colorful jerseys, standing with their bikes in front of a building with large windows and white curtains.

FAQ

General Information

  • The Owl Ride for Jackson is a two-day, 111-mile roundtrip bike ride from Chicago to Valparaiso, IN, and back. A one-day option covering 55 miles is also available. Proceeds benefit the Jackson Chance Foundation’s (JCF) NICU Transportation Program. Click here to view why parking matters!

    Click here to view our Recruitment Packet!

  • The ride takes place on Saturday, August 15, and Sunday, August 16, 2026.

  • The ride starts on Chicago’s lakefront and concludes at Valparaiso, IN, for day one. Day two brings riders back to Chicago.

  • Proceeds support JCF’s NICU Transportation Program, which provides free parking passes for families with critically ill babies at partnered hospitals.

Registration and Costs

  • • Two-Day Riders: $1,111 fundraising minimum + $165 hotel fee

    • One-Day Riders: $600 fundraising minimum

  • Click here to sign up.

  • Yes! You can create or join a team during registration. Teams fundraise collectively, and each team gets a unique fundraising link. Click here to create a team!

  • Yes! You can become an ambassador and create a personal fundraising page without riding. No fundraising minimum is required. Click here to become an ambassador!

  • Email info@jacksonchance.org.

Preparation and Training

  • You will need a bike, helmet, and appropriate cycling gear. Riders will receive a checklist before the ride.

  • Yes, Team Chance offers weekly training rides starting in the summer on Wednesday evenings and Sunday mornings. Training is designed to prepare participants for both the one-day and two-day options.

  • With fitness and activity 3–4 days a week, most participants can complete the ride with minimal additional training.

  • The route features a mix of cement and gravel trails with some city streets. It includes rolling terrain and occasional climbs.

  • The distance may vary slightly depending on the route and conditions. The 111-mile milestone honors Jackson Chance Meghie’s birthday on 11/11/11.

  • Riders are grouped based on their anticipated pace (typically 13–18 MPH). Group leaders can adjust speeds as needed.

  • Yes, each group has a support cyclist for minor repairs and first aid. Road crew transportation is available for emergencies.

  • All riders are invited to a post-ride celebration on Sunday with dinner, treats, and massages.

  • A shuttle will transport one-day riders back to Chicago after the Saturday ride, departing at approximately 2 PM.