Events, Fireworks Cruises, Wine Tastings

Make Memories With Us

Chicago Sailing offers a number of special events that can be designed as romantic outings, bachelor/bachelorette parties, or even just a fun night out with friends!  With options ranging from weekly fireworks cruises, monthly wine tastings, even dockside bashes with libations and live music we have you covered!

Don’t see exactly what you are looking for?  Give us a call and let us work our magic!

Wind & Wine

Join us for our bi-weekly sailing and wine tasting event! This is an excellent social sailing opportunity for those looking to give sailing a try

Diesel Engine Workshop

Learn the ins-and-outs of marine diesel engine mechanics as we tear apart a modern engine.

Fireworks Cruises

The perfect way to experience Chicago’s weekly lakefront fireworks shows! 

Delivery Trips

Join us as we set sail from one of many ports around Lake Michigan on our way back to Chicago. Email us for upcoming trips

BVI Cruising Course

Set sail for adventure with our 7 day BVI Cruising course!  

Team Building Events

Treat your team to a one of a kind sailing adventure!