Sharpen your skills, learn about strategy, and meet new friends in a low key racing environment.

OFFSITE and weekend REGATTAS

Sail Chicago fields boats for several regattas in the Chicago area, offering opportunities for longer racing distances and practice with starting sequences. In recent years, Sail Chicago has participated with multiple boats in the Verve Inshore Regatta (held in late August) and the Rainbow Regatta (held in July). Plans are underway to add Columbia Yacht Club's Colors Regatta in 2026.

Wednesday night racing

Monroe Harbor

Sail Chicago is committed to instruction, and our racing program is an extension of our class offerings. We offer weekly Wednesday night windward-leeward racing for as long as the season allows. Skippers and crew are challenged to optimize speed and performance, using spinnakers and learning how to properly rig, hoist, trim, and douse them. Racing is a blend of camaraderie, learning, team-building, and competition. Teams typically gather at Columbia Yacht Club (our Wednesday night sponsor) or on the lawn outside the Monroe tender station after races.

Members must have completed Level 1: Crew in order to participate in Wednesday night racing.

Cost: $100 per season



racing tiller times

Racing Tiller Times, similar to regular Tiller Times, are an opportunity to fine-tune racing skills outside of a competitive setting. Experienced skippers, foredeck specialists, and other seasoned racers are on hand to answer questions.

Unlimited Racing Tiller Times are included in your Wednesday night racing fee.

FREQUENTLY ASKED QUESTIONS

  • Yes, anyone who has completed Sail Chicago's "Crew" (Beginner) class is welcome. Many folks have developed time at the helm and more confidence by racing.

  • That's totally fine. Most people aren't able to commit to racing every week during the summer. You will be allowed to sign-up each week. An email is sent typically on Sunday morning for the upcoming Wednesday race.

    For more information use the Racing channel on the Slack Page.

  • Sail Chicago uses its Colgate 26 fleet for racing.

  • That's not a problem at all! We make sure that there is at least one person who is experienced at the foredeck and also a racing skipper on each boat. We will be happy to introduce you to the thrill of correctly rigging and safely hoisting, trimming and dousing the spinnaker.

  • In order to make for a safe and enjoyable experience for everyone, we do require that racers have completed the Sail Chicago "Crew" class and/or have the equivalent experience. Please see the the Instruction page for a list of skills that students in each class are expected to have acquired.

  • The cost is $100 to purchase a season ticket/pass which allows you to sign-up for weekly races.

  • Unfortunately, we are unable to accommodate visitors. As much as we like to meet people who share our passion for racing, our insurance coverage does not allow us to do this. Sorry!

  • As of 2022, We have started to offer on the water Racing Tiller Times. These sessions cover topics such as the US Sailing Rules of Racing, roles/positions, spinnaker usage, starts, and general tactics

  • Weekend races (exact dates TBD) will be offered as an opportunity for longer racing distances and also an opportunity to practice racing starting sequences. This would be offered as a private sail (not included in the $100 Wednesday night racing "season ticket").

  • In addition to Wednesday night racing, Sail Chicago fields boats for weekend regattas. For the last several years Sail Chicago has participated with multiple boats in the Verve In-shore Regatta held in late August. We intend to add participation in the COLORS regatta as well.

    Participation in Regattas is funded by participants (not included in the $100 Wednesday night "season ticket").

  • Sail Chicago offers weekly Wednesday night windward-leeward racing for as long as the season allows weather-wise. We typically start the season in mid-May based on SC boats being available in the harbor and end the season in late September/early October. The cost to participate in Wednesday night racing is $100 for the season.

    You can purchase a "racing ticket" on the Racing page or on my.sailchicago.org under "Courses and Classes" section of the Instruction Tab. Look for the "Racing Season Membership" course.

    Sail Chicago is committed to instruction and our racing program is in some ways an extension of our class offerings. We challenge skippers and crew members to optimize speed and performance. We also use spinnakers! It is a good blend of camaraderie and competition. Following a Wednesday race we typically gather either at Columbia Yacht Club or simply out on the lawn outside the Monroe tender station.

  • It depends. We require the skills that are taught in Sail Chicago's "Crew" (Basic) class. We understand those skills might be acquired by another program or experience. Please see our Instruction page to learn about the skills needed. If you're still unsure reach out to the Racing channel on the Sail Chicago Slack for more information.

  • Yes, you need to be a current member in good standing to participate in our racing program.