Ultimate Ultimates: Chicago’s Top-10 Toughest Finishing Golf Holes

TOP-TEN-TOUGHEST-FINISHThe Merriam-Webster online dictionary provides multiple definitions for the word “ultimate”, two of which are a) the best or most extreme of its kind (synonym: utmost), and, b) the last in a progression or series (synonym: final). Using this word twice provides a great topic for an article and list pertaining to our area’s most difficult finishing holes. While some readers of Chicago Golf Report may believe that picking up the tab on the 19th hole is the harshest finish, we placed relevance on the factors of beauty and nastiness, and compiled our list of Chicago’s toughest finishing holes, parring any of which could put you on the receiving end of 19th hole refreshments.


10. Prairie Landing Golf Club – Par 5; 570 / 545 / 525 / 504 / 459
The home hole is a longish par five with options galore, just be sure that your ‘landings’ on this finishing hole are fairway and green, not sand and water. A string of three bunkers are in the middle of the rambling fairway. The gamblers will hit left of the bunkers leaving a 235-yard carry over water for a potential eagle. A more conservative route is to play right of the central bunkers, then to the fairway right of the lake. A short iron shot remains to the green nestled amongst mounds. The fairway tips away from the water near the green as the putting surface, protected by the facing bunker, rises to a bowl on the back right.

Chalet Hills Golf Club - 18th Hole

Chalet Hills Golf Club – 18th Hole

9. Chalet Hills Golf Club – Par 5; 494 / 474 / 430 / 367
It’s a semi-circular, counter clockwise trip around the right side of a large lake. Fairly straightforward advice: don’t go left on your drive, don’t go left on any fairway shots, and don’t go left on your approach shot to this green. It’s a nightmare for golfers who hit pulled shots, big draws, and snap hooks. Staying right, a safe distance away from the edge of the lake will keep shots dry but will also lengthen the hole; playing safe-and-dry too far right will bring the out-of-bounds of the back yards of expensive homes into play. The quirky par of 73 for Chalet Hills Golf Club means that ‘bogey golfers’ through the first seventeen holes would need a birdie here to break 90.

Whisper Creek Golf Club - 18th Hole

Whisper Creek Golf Club – 18th Hole

8. Whisper Creek Golf Club – Par 5; 527 / 509 / 469 / 436
Originally routed as hole number nine, a decision to flip-flop the nines placed this testy hole with its dramatic scenery as Whisper Creek’s finale. Multiple rounds of trial and error have probably taught members and repeat players how to properly dissect this ‘beauty and the beast’ hole. First-timers on Whisper Creek’s finisher should carefully study the picture and note all the distances found in the players guide and / or gps. The hole map illustrates that there is a forced carry over water in the mid-section of the hole. Start by calculating the driving distance needed to result in a desirable forced carry yardage for the second shot. The minimum distance over water from the far edge of the first fairway to the close edge of the second fairway is approximately 64 yards. The two fairway framing bunkers on the right side of the second fairway are on a good target line for the second shot, but an over-powered second shot ending up in one of these two sandy hazards will necessitate a long explosion for the third shot. After a well placed drive, long hitters may consider going for the green on their second shot, but as the hole map shows, the flight is entirely over water, so it’s stroke-and-distance penalty if the shot fails to clear the pond. Waterfalls, flora, and a tricky putting surface make the finish of this finishing hole quite memorable.

Glen Club - 18th Hole

Glen Club – 18th Hole

7. The Glen Club – Par 5; 589 / 561 / 530 / 456
Tom Fazio’s masterpiece in Glenview culminates with a masterpiece par-5 hole — a lengthy ‘canvas’ onto which he has painted the troubles of sand, water, and rough. The hole is a long par 5 that can be reached in two by the long hitters. Wind is a key factor for strategy here on #18; a south wind is helpful, take more club when the wind blows from the north. The tee shot is elevated to a wide fairway but must carry over a patch of gorse; players will be looking to drive over the gorse and catch the fairway downslope just past the right fairway bunker. Those shorter hitters will need to contend with a fairway bunker and pond on the right and a fairway that gets narrower the closer you get to the hole. Players should lay up to a yardage that is comfortable to them and be left with a short iron or wedge into a green guarded on the front and right by a pond and bunkers and on the left by another bunker. Players going for the green in two will be hitting a long iron or fairway wood over a pond and bunkers to a shallow green – this is a very risky shot but can also be very rewarding with a sub-par score; successes and failures can be viewed by folks relaxing on the clubhouse patio which overlooks the eighteenth green.


6. Mistwood Golf Course – Par 5; 527 / 527 / 503 / 485 / 390
If Cary’s Chalet Hills finisher is a nightmare for hookers, then Romeoville’s Mistwood finale is no pleasant dream for slicers. With the tee set back in a wooded area forcing a straight drive out of a narrow chute, the hole plays as a mild dog-leg right, but dense woods guard the entire right side of this hole along with two small ponds. No less than nine grass and sand bunkers guard the left side of the fairway inhibiting bailouts that are too wide to the portside. Finally, a creek crosses in front of the green that is also protected by three stacked sod bunkers. This hole is named “Home”; you’ll be headed to your home proudly or sorrowfully depending on your score here.

5. Village Links of Glen Ellyn – Par 4; 422 / 397 / 375 / 353 /329
A fitting finish to a course whose rating is 74.9/138. Village Links’ 18th hole is one of only two par-4’s that occupy Chicago Golf Report’s Top-10 Toughest Finishers list. Two large ponds challenge and befuddle golfers as they stand on the #18 tee and ask themselves ‘where should I, where can I hit my drive’? Long and straight over pond number one and left of pond number two could be ‘Plan A’;
or, long and straight over pond number one and right of pond number two could be ‘Plan B’. Short hitters must develop alternate plans ‘C’, ‘D’, or ‘E’ to reach this green. The green is quite large, pitched, and with a few sneaky undulations, so prepare good battle plans for chipping and putting as well.

Links at Carillon - 9th Hole White Course

Links at Carillon – 9th Hole White Course

4. Links at Carillon – White Course #9 – Par 5; 528 / 510 / 494 / 432
There are approximately 70 sand bunkers scattered throughout the grounds of Carillon, and water comes into play on 16 of its 27 holes. Nowhere is the water more plentiful or intimidating than on the 9th hole of the White Course, nicknamed “The Gauntlet”. This hole, with its two large ponds mandates two forced carries (or perhaps three, depending upon mis-hits). Since this hole is pretty wide open without much protection from the elements, the wind can play a major factor on every shot of “The Gauntlet”. An imposing tee shot requires a minimum carry of 180 yards over water from the back tees. However, there is a second pond just beyond the fairway, so the drive must stay to the left side of the fairway to avoid the second water hazard. The second shot on this hole requires precise distance control and a strategic placement. Most players attempt to favor the right side of the fairway to potentially minimize the danger of their upcoming third shot. The approach to the green on this hole is also a forced carry directly over an inlet that protects the putting surface–a bigger challenge if the hole location is back left. The hole map of White #9 appears to show more blue than green, hence “The Gauntlet” is considered to be one of the most demanding holes in the entire southern portion of Chicago.


3. Cog Hill Golf & Country Club – Dubsdread – Par 4; 494 / 459 / 431 / 401 / 374 / 371
Any hole that can give fits to and produce bogeys for PGA Tour players will certainly give fits to and produce bogeys for Chicago amateur golfers, and thus warrants a position on our Top-10 Toughest Finishers list. TV viewers and attendees of previous Western Opens or BMW Championships recall that this hole demands a straight drive, as trouble in the form of hardwood trees and fairway traps occupy both sides of the fairway. The two fairway bunkers pinch in from both directions and produce a narrow landing area. Trouble lurks on both sides of the kidney shaped green — pond left and bunker right. The speedy green is pitched dramatically toward the pond and produces many 3-putts and / or wet chip shots.

Steeple Chase Golf Club - 18th Hole

Steeple Chase Golf Club – 18th Hole

2. Steeple Chase Golf Club – Par 5; 543 / 526 / 487 /417
Golfers at Steeple Chase must ride their “A” game like a thoroughbred to grab a par or better on this finishing hole in Mundelein. Voice activation or remote control are the only two possible methods to position a long drive properly to have a chance to reach this finishing green in two shots. The zig-zag nature of the first two-thirds of this fairway makes it a true three-shot journey to get to the green. Approach shots that are intentionally hit long to assure carrying the water, can end up in the back left bunker; the water again becomes a frightening sight, as the slope from the back bunker across the green towards the water is a steep decline. What we have here is the personification of beauty and nastiness.


1. Stonewall Orchard Golf Club – Par 5; 615 / 562 / 514 / 441
Stonewall Orchard has been the host site of US Open local qualifying in 2003, 2005, 2009, and 2015. More recently, Stonewall Orchard was the host site of Monday qualifying for the Rust-Oleum Championship on the Web.com Tour. Let it be known that the grounds of Stonewall Orchard contain more than 65,000 mature trees. Golfers may think that most of these trees occupy the 18th hole. Just as Tina Turner says in her song ‘Proud Mary’, Arthur Hills never, ever, does anything nice ‘n’ easy. Architect Hills not only uses trees as a defense against par on Stonewall’s finale, but he reached into his bag of design tricks and emptied it to create Chicago’s toughest public access finishing hole — length, trees, undulations, sand, and water.

The longest par 5 on the course requires three long, straight shots to reach the green. An accurate drive to the not-as-straight-as-is-looks fairway and a second shot between two large oak trees sets up a difficult and challenging approach shot. A lake on the left and behind, and two bunkers right guard the smallest green on the course. Approach shots that bail out to the right of the green will settle into bluegrass rough and be tested with a downhill chip shot. Good luck against the forces of Arthur Hills.

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Greg Miles

Greg Miles has been a writer following golf in Chicago since 1990. For the past 28 years he has been a member of the Golf Writers Association of America and currently is classified as a GWAA "Life Member". He played his first round of golf on his 11th birthday, and since then has played more than 7,000 rounds of golf in his lifetime at 514 different courses. He has interviewed more than 275 golfers across all the professional tours along with famous celebrity golfers. Additionally, he is a member of several other competitive and honorary golf associations, as well as the Golf Nut Society.

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