I completed my bareboat certification years ago (2001-ish) with a company called Sailboats Incorporated.
The do instruction and bareboat chartering.
They have a long standing presence right in the heart of downtown Chicago--Monroe / Du Sable Harbors to be exact. It's an excellent location. They have a few other bases too (Lake Pippin, MN and Bayfield, WI near the Apostle Islands of Lake Superior).
After the course, I chartered with them quite a few times--sailed their boats around Chicago, and as far away as New Buffalo, MI. They were always great to work with. Their fleet is older, but maintained acceptably.
Wednesday and Saturday evenings at Navy Pier there are short fireworks displays. It's not much of a display--but to take it in from a boat is awesome.
Another company of interest is Michigan City Sailboat Charters (although it would be a crunch to sail to Chicago, take it in, and return in two days).
02-04-2010 12:26 PM
Consider Chicago Sailing
Hi MikeyMo! My company might be the right sailing facility for you. We are Chicago Sailing and offer all of our vessels for hourly rentals. As a public facility, we consider anyone on our dock a member!
Our website is chicagosailing.com Consider renting our J/30, T-10 of Hunter-326's. You can rent a vessel for a few hours, or if you want we can offer discounted day rates.
Contact me for more information!
02-03-2010 08:48 PM
Chicago Charter Recommendation
I'm a Chesapeake sailor that will be visiting Chicago this summer and would like to charter a sailboat, 30-36 foot preferred, for at least a day sail and perhaps an overnight or two. Any of our Great Lake sailors have a recommendation on a Charter Company and destination. Please.