There is a great sailing culture here but the season is pretty short.
Living aboard is all but impossible year round. There is one very small place on the river (no scheduled bridge lifts after season so you'd be stuck if you had
mast up) that has limited year-round accommodations using extensive bubblers in the
winter but I believe it is nigh impossible to get a spot there. I think you need to own property in the attached high-rise condo.
Most all of the city harbors close October 31, but you can get a late-leaver extension at one of the harbors here for a couple more weeks. Not many folks take advantage of this but a few hearty souls. The
weather is getting pretty rough once October rolls around. November is pretty brisk. Nearly all of the boats
lost off of moorings during storms are during the last few weeks of the season. We loose a few every year. Last year a
boat just a couple of cans over from us broke free and broke up on the wall against the lake shore bike path. It wasn't the only one
lost in our harbor last year either.
Getting a slip downtown probably isn't going to happen the first year and you'd have to go with a
mooring. Getting a slip further north or in 31st street down south is maybe easier but prices are dear. 31st is in bufu so they always have spots. Not great access and once they start storing boats onsite boater lose parking access. Daft...
There are always moorings available in Monroe Harbor right downtown. Some are pretty exposed though. Protection from waves coming in from the SE is horrible and it gets pretty uncomfortable when that happens. It gets so bad that sometimes the tenders can't make it out to the boats, or they need to move their launch area to a different spot when their regular
tender dock is too dangerous to operate out of. It gets that bad quite a few times in the autumn, maybe once or twice a week at the end.
Action starts again in May although a lot of folks wait until June because it is fairly chilly and sporty in the spring.
We lived aboard in Monroe Harbor on a
mooring can the last two summer as much as we could. 5-6 nights a week. There is a
tender service included in the mooring
permit but the hours are not the greatest in the morning if you
work early or anywhere that will take a longer commute from the downtown. You must pay a couple hundred dollars extra to use your own dingy and there really is nothing as far as accommodations or
security. Your dink
will get vandalized and probably stolen at least once a season but usually they find them when the thieves are done joy-riding.
I know of only one guy who attempts to use his own
dinghy regularly in the downtown harbor and he's had to go searching for his
boat a few times. It's just a
cheap plastic WestMarine tender and looks like it went through a war.
There is a large
racing community with regular races on the weekends and on Wednesday nights. If that is what you are into there is plenty here. I'm not into it so can't help you there.
It's an exciting place to sail because there are many neat features,
Navy Pier, the river locks, lifting bridges, the outer seawalls, the lighthouse, the many harbors and even a few big
water utility buildings (cribs) a few miles
offshore along the lake to go out and sail around. Plus there is a lot of traffic here with all the sailboats,
race boats,
motor boats,
cruise ships, dinner cruises,
water taxis, speed boat rides, and even a tall ship to share the water with. You'll get more comfortable sailing nearby hundreds of other boats nearby after a while.
Winter
storage is a big thing here and there are many places that do it. The water freezes up pretty hard most places, or has the potential to, so not many boats stay in the water except some of the big guys. There is some limited wet
storage here and there, usually for wooden boats that don't want to haul I have been told. There are a couple at the place I'm at this year on the river. This time of year I don't even go down to the lake as it's too cold and depressing, but I'm at my boat
on the hard almost every day getting it ready for leaving Chicago for good this coming spring.