2025 Chicago Regatta

The Chicago Regatta provides a fun opportunity for all boaters to contribute to the well-being of children while celebrating the boating community that enriches our lives.

The regatta benefits children through the Chicago Yacht Club Foundation, Big Brothers Big Sisters of Metro Chicago, and One Family Illinois (formerly SOS Children's Villages Illinois).

The Chicago Regatta remains the showcase and celebration of the waterfront community's shared generosity, love of the water, and compassion for children.

The regatta lasts a day, but your impact endures. Make plans now to join the fun and maximize our community’s contribution.

Register to race above! For more information on the charities we benefit, more ways to get involved, and to donate, please visit us at www.chicagoregatta.com. 

Update from the Organizers 9/3/2025:

Thank you for competing in this year’s Chicago Regatta and contributing to the well-being of Chicago’s children. This year we weren’t able to generate as many registrations in all the different types of racing we originally planned to offer so we had to consider what the best plan of action is for the event and came to the tough decision to simplify the racing options to only conduct the Chicago Shuffle Distance Race under the PHRF rating system and the Second City DF65 race for this year’s regatta. We know this is disappointing news to some of you, but we hope this will create a more fun and competitive atmosphere on the water to continue ashore at Monroe station after racing.

So, what happens now: your registration will be transferred to the distance racing class and your PHRF rating entered into the system by the race office, so it is no additional work on your part. If you select to not sail this year due to this change, please reach out to regattamanager@chicagoyachtclub.org and we’ll refund your entry fee unless you would like us to consider it a donation where you’ll be able to direct it towards any of the 3 charities we support: Big Brothers Big Sisters, One Family, or the CYC Foundation (or divide it equally among the 3). Whether you race or not, we hope you’ll join us at Monroe for the My-Kind-of-Town party including raffles and silent auction starting at 5pm. Tickets are available for pre-purchase https://www.chicagoregatta.com/celebrate.

We thank you for your understanding and look forward to seeing you Saturday!

Sincerely,

The Chicago Regatta Committee