My personal favorites from Chicago, each hole is the appropriately numbered hole from its course. There are many other courses that I could include, most notably Chicago Golf Club, but I only played there once and the memory ain't what it used to be. Strictly a personal list!
#1 Skokie: A man-sized par 4 of 440 yards with terrific fairway and greenside bunkering.
#2 Bob O'Link: Mid-sized par 4 with a pond to the left and a demanding green.
#3 Olympia Fields North: 460 yard par 4 with a second shot to a small, elevated green. The creek isn't really in play but it sure is pretty!
#4 Shoreacres: Quite possibly one of the best mid-sized cape holes that you'll ever play, with a meandering burn that insinuates its way up and across the fairway.
#5 Beverly Country Club: The best 400 yard par 4 in Chicago, with an impressive plateau green.
#6 Olympia Fields South: A spectacular short par four with a volcano green protected by a creek in front and dramatic dropoffs on all sides.
#7 Dunes Club (well, it's in the Chicago district!): A little bit of Pine Valley in Harbor Country, a very scenic par three cut out of the forested sand dunes. Multiple tee boxes present different angles that present different challenges. The green is one of the best protected this side of Sand Hills. Simply the best par 3 I've ever played.
#8 Butler National: 180 yard par 3 with a pond that runs up to the front of the green. Tough stuff.
#9 Cog Hill (#4): A serpentine and well bunkered par 5 that kills us mere mortals but the pros demolish.
THE BACK NINE
#10 Butler National: A brutal 450ish par 4 from the members tees with hazards to the left and right, Salt Creek just in front of the green, which is a shallow, horizontal torture chamber.
#11 Flossmoor CC: 175 yard uphill par three with a relatively blind tee shot to a tricky green.
#12 Medinah (#3): Quite possibly the best par 4 in Chicago, a big par 4 that bends slightly to the right, with a dramatically tilted fairway and a big pond just to the right of the green.
#13 LaGrange CC: A midsized par 4 with terrific fairway and green bunkering. A hidden gem of a golf course.
#14 Olympia Fields North: A 445 yard par 4 with a creek that pops into view 100 yards in front of the tee, runs up the right side of the fairway to 300 yards from the tee, cuts left across the fairway and then takes a hard right where it waits for pulled second shots. A tough back to front tilted green awaits you.
#15 Shoreacres: a short par 5 (490 yards) with an ingenious split fairway on two elevations and a creek cutting across the fairway.
#16 Cog Hill (#4) Big, sweeping par 4 with a pond to the left. One of the more scenic 4's in Chicago.
#17 Medinah (#3): Terrific par three over Lake Kadijah. Hard to beat this one.
#18 Beverly Country Club: 600 yard dogleg to the right with well placed fairway bunkers that come into play on your second shot. The shot into the green is very tight, but the green is enormous and tilted from back to front. Spectacular finishing par 5 with a great view of the clubhouse.
Par 71, roughly 7200 yards.