Below are the courses that I am somewhat familiar with, meaning either I've played it in the last couple years, or I've played it multiple times. I then separated them by rough tiers, and their year of opening next to them.
Beverly (1907) - Haven't seen it since 2001, but I liked it then and from pictures and what I'm told it's even better now.
Black Sheep (2002) - Very good design in the way western suburbs.
Bob 'O Link (1916) - This is borderline top tier
golf courses IMO...usually gets bumps from others because they mistake the atmosphere for GCA.
Butler (1974) - Much discussed, haven't seen it since Fazio came in a few years ago to spruce up the layout though.
Chicago Golf (1894) - The great-granddaddy
Dubsdread (1964) - Certainly the flagship of the very strong public golf scene
Medinah (1928) - Long and hard, but a mainstay in Chicago and tournament golf.
Old Elm (1913) - Old Elm comes in a close 2nd to SA of courses in Chicago that I most enjoy playing.
OFCC - North (1922) - Great, and pretty underrated, championship golf course.
OFCC - South (1916) - Fantastic renovation by Smyers.
Shoreacres (1921) - Maybe not the "best" even though it's a fantastic course but my favorite place to play in Chicago.
Skokie (1915) - Very strong golf course, even if many hands have touched it at different points.
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Conway Farms (1991) - New Fazio in Lake Forest. Nice place to play but the GCA is lacking in some spots.
Evanston (1914) - Jack N. butchered the course in a "renovation" in the 1980's, Ron P. was recently brought in to fix that.
Exmoor (1915) - Played a lot in high school and always enjoyed it alot, since been renovated.
The Glen Club (2001) - I used to caddy there and actually think it's pretty good Fazio effort.
Kemper Lakes (1979) - Maybe not in fashion today, but I always liked the course and think it's the best of the Nugent/Chicago style GCA.
Knollwood Club (1923)*
Lake Shore CC (1908)*
North Shore CC (1924)* *All nice places to play, but none will blow your socks off IMO.
Onwentsia Club (1896) - Pretty neat since Doak came in and essentially built a new golf course.
Wynstone (1989) - The front nine at this Jack N. course is pretty darn good, back nine gives me headaches.
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Pine Meadow (1985) - Solid public course built on Flynn bones.
Ravisloe (1915) - Fun course recently made public and much talked about here.
Rich Harvest Farms (1998) - Good in spots, but overdone in many others.
Sunset Ridge CC (1924) - Nice North Shore layout.
Thunderhawk (1999) - Solid RTJ, Jr. design in a Forest Preserve up by the WI border.
Westmoreland (1911) - Not my favorite but pretty good, has had major issues with their greens over the past 10 years.
Wilmette GC (1922) -
