Chicago Golf Eclectic 18

In the lead-up to this week’s Presidents Cup at Medinah Country Club, our team put together a deep-dive video on the recent renovation to the host Course 3 and curated an in-depth guide to Chicago. That got me thinking: what are some of the best holes in and around city?

For this exercise, I allowed myself to pick one hole per course, and the routing must be a true 1-18. Now, you might think routing an Eclectic 18 would be an easy task. Just pick your favorite holes. How hard can that be? With Chicagoland as the theme, it turns out to be a pretty difficult challenge. Keep in mind that most of the great golf in the area is private, so by nature this list doesn’t feature the most-accessible places to play (click here for that list).

Without further ado, here’s my Chicago Eclectic 18:

No. 1, Par 5

Flossmoor Golf Club

A gettable opener that is made tricky by the green, which falls away and to the right. This is the start to one of the best sets of greens in Chicagoland. 

No. 2, Par 4

Old Elm Club

One of the toughest holes in Chicago thanks to its elevated volcano green that repels shots in all directions. 

No. 3, Par 3

Chicago Golf Club

One of the many awe-inspiring greens at Chicago Golf Club. The third is a monster par 3 that requires a run-up shot for lower-trajectory players. My favorite feature is the two spines that run through the fairway run-up area, known for corralling shots and kicking balls that are a bit too offline into the bunkers.

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No. 4, Par 4

Skokie Country Club

A brawny hole that jogs left and features one of Skokie’s greens that was built by Langford and Moreau. The bold contours allow for running shots into this long par 4. 

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No. 5, Par 4

Knollwood Club

This mid-length hole plays downhill from the locker room and features a neat green complex which obscures your view from the right. Drew Rogers added a series of moguls in the right rough which add to its character. 

No. 6, Par 4

Medinah Country Club (Course 3)

The new sixth at Medinah features an out-of-bounds fence down the entire left side of the hole, which begs players to take it on off the tee to get a better shot into the green. If you play away to the right, then you will have to deal with the fence on the approach shot to left hole locations.

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No. 7, Par 4

Conway Farms

One of Conway Farms’ tricky short par 4s. The seventh features a shallow and undulating green complex. The ideal miss around the green depends on the day’s hole location. The option to lay up off the tee is always available, which leaves a full wedge shot in. 

No. 8, Par 4

Olympia Fields Country Club (South Course)

This stellar short hole features one of the scariest approaches in Chicago to a tiny, elevated green. Nicknamed “Hell’s Kitchen,” it certainly has a fitting title. 

No. 9, Par 4

Medinah Country Club (Course 2)

One of the most fun shots in Chicagoland. The oft-overlooked Course 2 at Medinah is filled with shorter par 4s, and the ninth green is unique with its monster backstop. Front pins have to deal with the fronting lake and back pins have the option to use the big backstop to get it close — just a fun shot to hit. 

No. 10, Par 5

Onwentsia Club

This hole runs along the property line on the right. It makes for a challenging tee shot, as the fairway then cants left. It is difficult to hold the fairway unless you hit it up the right center. The green complex is great with a big false front and then a back portion that falls away. A really fun golf hole. 

No. 11, Par 4

Shoreacres

Possibly the most jaw-dropping hole in Chicago, this hole plays through a ravine that cuts in front of the tee box and runs along the right side of the fairway before wrapping in front of the green. The 11th at Shoreacres is one of the most naturally intimidating holes in Chicago. 

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No. 12, Par 3

Beverly Country Club

A wonderful little par 3. Beverly’s 12th is surrounded by bunkers, and the green shape amplifies their impact. Little lobes at the corners allow for tucked pins that make for a tricky test. 

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No. 13, Par 4

Medinah Country Club (Course 1)

A stellar short par 4 on flat land which is made by the green and the big mound on the right side. The ideal line off the tee is up the left, but the property line and a bunker sit where you want to hit it. Bailing right is an option but makes for a very tricky up and down. 

No. 14, Par 4

Olympia Fields Country Club (North Course)

The 14th is probably the most beautiful hole at Olympia Fields. It tees off on a ridge above the Butterfield Creek before playing down into the low area along the creek. The approach shot then plays back up to the green that sits on a ridge; an absolutely stellar golf hole. 

No. 15, Par 3

Kankakee Elks Country Club

A stunning hole which plays from a low point on the property up a monstrous ridge on which the green sits. This is as dramatic a par 3 as there is in Chicagoland. 

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No. 16, Par 4

Ravisloe Country Club

A wonderful mid-length par 4 that plays over Ravisloe’s best terrain. The tee shot needs to hug the right side to hold the fairway and find short grass to set up the ideal approach to a tricky fall-away green. 

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No. 17, Par 4

Glen View Club

It’s a blind shot off the tee to a fairway that sits in the course’s river valley. Finding the right side leaves a better approach to this severe green that sits on a ridge. 

No. 18, Par 4

Exmoor Country Club

Your quintessential big par 4 finisher with Exmoor’s wonderful clubhouse in the background.