Omega,
Clearing would be a Really tough condition right now, it was torn down a few years ago and is now a gravel parking lot that the city uses to store machinery. It was a really tough house though, with the above gound returns, poles on the other side, no oil, and divots the size of potholes in the lanes. The other Marzano house, Miami, is closed now too, so two of the oldest and toughest houses on the Southwest side are no more.
H,
There's a place like michelle described in Frankfort, way southwest of the city. It's a second floor, six lane house with above ground returns. The place is in good shape, no ball damage, but it can get pretty squirrelly. If you get there on the wrong day it can be like the Sahara.
One of the hardest houses for a long time was Lawn Bowl on 67th and Pulaski, not too far from Midway Airport. So if you're flying in, it may be close. They have some of the original Brunswick synthetics, and never used to strip them, I know I used to be a mechanic there. They got a new machine that strips them now, so they're not as hard as they used to be, still pretty difficult though, the owner doesn't believe in giving anything away. It's especially fun if you bowl on 1 and 2 as a righty or 15 and 16 as a lefty, because the wall runs right along the edge of the gutter, no room to get deep without kicking it.
If it's still open, Town Hall in Cicero can be pretty hard, although I think they have new owners who softened it up a little bit. It's on 25th St. and has/had one of the biggest money leagues in the city because everyone was under like 202. You really had to work to shoot anything big, and forget about putting a few games together.
Rolling is really difficult. I think they oil with a garden house. Eveyone I know that bowls there complains about not being able to wrinkle a ball, even if it's an Animal with surface or a Fear Factor, or what ever. You really need to have a lot of hand to get any carry or throw BBs at the pocket.
Bluebird Lanes, formerly Laredo Lanes on Sothwest Highway and Pulaski used to be really brutal. You had to play the 1 or 2 board most of the time and basically hang it over the ditch. They have like 16 lanes on one side and another 6 or 8 on the other. The small side was always pretty brutal when I went to practice.
I really only know the South Side, but those are the only ones I can really think of. Anyone have any different opinions?
The rest of the houses are like Omega said. Orland Bowl, Arena (Brunswick Zone now I think?), Tinley, Palos, Centennial (Centenni-Wall to us local), Burr Oak, and the rest are all pretty easy, either get inside and grip it and rip it, or fluff it up the track.
I Hope Some of this Helps,
Mankow