The Sail Chicago Racing community is a group of great people who love to learn, teach and compete -- and also have fun while doing all those things!

Wednesday Night Racing

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 Sail Chicago 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 this season. You can purchase the season "ticket" here or by logging in to my.sailchicago.org and choosing Instruction -> Course Availability.

Sail Chicago is committed to instruction and our racing program is in some ways an extension of our class offerings. We challenge skippers and crewmembers to optimize speed and performance. We also use spinnakers! -- We teach our racers how to properly rig and safely hoist, trim and douse the spinnaker. It is a good blend of camaraderie, learning, team-building and competition. Following a Wednesday race we typically gather either at Columbia Yacht Club (our Wednesday night sponsor) or simply out on the lawn outside the Monroe tender station.

Offsite Regattas

In addition to Wednesday night racing, Sail Chicago fields boats for weekend regattas in the Chicago area. 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 Columbia Yacht Club's COLORS regatta this year's schedule.

Participation in Offsite Regattas is funded by participants -- NOT included in the Wednesday night Racing Season Membership.

Weekend Racing

Weekend races (exact dates TBD) will be offered as an opportunity for longer racing distances and also an opportunity to practice racing starting sequences.

Weekend Racing is NOT included in the Wednesday night Racing Season Membership.

Racing Tiller Times

Racing Tiller Times, similar to what Sail Chicago offers for current or prior year students, provides the opportunity to fine-tune your racing skills outside of a competitive situation. Experienced skippers, foredeck specialists and other experienced racers are onboard to answer these questions.

Racing Tiller Times are NOT included in the Wednesday night Racing Season Membership.