THE SAIL CHICAGO RACING COMMUNITY IS A GROUP OF SAILORS WHO LOVE TO LEARN, TEACH AND COMPETE — AND HAVE FUN WHILE DOING SO!
OFFSITE REGATTAS
Sail Chicago also 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 and plans are in the works to add Columbia Yacht Club's COLORS regatta in 2026.
Participation in Offsite Regattas is funded by participants and NOT included in the Wednesday night Racing Season Membership.
WEEKEND RACING
Weekend races are offered as an opportunity for longer racing distances and to practice racing starting sequences.
Weekend Racing is NOT included in the Wednesday night Racing Season Membership.
Wednesday night racing
Monroe Harbor
Sail Chicago is committed to instruction and our racing program is an extension of class offerings. We offer weekly Wednesday night windward-leeward racing for as long as the seasonal weather allows. Skippers and crew are challenged to optimize speed and performance. Racers will use spinnakers and learn how to properly rig, hoist, trim and douse it. 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.
The cost to participate is $100 per season.
racing tiller times
Racing Tiller Times, similar to regular Tiller Times, is an opportunity to fine-tune racing skills outside of a competitive situation. Experienced skippers, foredeck specialists and other experienced racers are onboard to answer questions.