The Top 10 Longest Golf Holes in Chicagoland

Big hitter, are ya? These holes are for you

Calling all long ballers! The Chicago area boasts an incredible golfing landscape, catering to players of all skillsets. But for those who crave the ultimate test of power and precision, this list unveils the longest holes on Chicagoland public courses. Prepare to unleash your inner bomber, because these behemoths stretch far beyond the average par-5. We're talking titans exceeding a staggering 700 yards, demanding not just raw power, but strategic shot selection and course management. These holes push even the most seasoned golfers to their limits.

Dial in your driver settings, grab your most reliable long irons, and take dead aim.

Note: On each image, the tee box is on the left, and greens are on the right.
Hole 17 at Chapel Hill Country Club

1. 703 Yards - Hole 17

Chapel Hill Country Club

Johnsburg, Illinois
Course length: 6,113 yards
Out in McHenry county, the 17th at Chapel Hill is an absolute beast — the longest in all of Chicagoland. There’s actually two blue tees on this hole to choose from: the 703 full length distance, or a 605 yard version which is still plenty long. A wild thing about this course having the longest hole is that the entire course is only 6,113 yards. The 17th hole accounts for almost 12% of the entire distance. Furthermore, Chapel Hill CC is by far the shortest course in this top 10 list, by about 500 yards!

Luckily there’s no water or bunkers to contend with. However, the fairway is extremely narrow the entire length of the hole - only about 22 yards wide. With a small green.

Overall this muni is a humble affair, with course conditions on the lower end of Chicagoland golf venues. Although, isn’t it worth playing here just to say you’ve attempted a 700 yard par-5?
Hole 11 at Golf Club of Illinois

2. 678 Yards - Hole 11

Golf Club of Illinois

Algonquin, Illinois
Course length: 7,011 yards
With a course rating of 74.4 from the back tees, you knew this track was going to test you. The 11th hole at hilly Golf Club of Illinois is a mid-round challenge that has the potential to blow up your scorecard. The hole is named "Grant's March" and a Chicago Tribune article from May 1994 claims it was the longest par-5 in America at the time. Two strategically-placed fairway bunkers aim to gobble your golf balls, while five greenside bunkers look to add insult to injury on this 678-yarder. The green is one of the smallest at the club. Also, keep your slice in check; there’s OB to the right, with homes lining the entire starboard side of this gargantuan hole.
Hole 14 at Shepherds Crook Golf Course

3. 654 Yards - Hole 14

Shepherd's Crook Golf Course

Zion, Illinois
Course length: 6,827 yards
This gem of a course nestled on the Wisconsin border will challenge all aspects of your game. From the back tees, the 14th at Shepherd’s Crook can be played as either a 654-yard colossus, or a slightly more reasonable 617-yard affair. Of course, it’s a tough hole either way. The 654-yard tee box is just a small, round, isolated bump next to a utility area; this is where the psychological torture begins. From there, your drive must avoid fairway bunkers on the right side, so hopefully you have favorable wind and don’t slice it. At least the fairway is forgiving -- as wide as 50 yards in some parts.

If successful on the first shot, you now face the real test: a creek runs across the fairway at about 490 yards from your original tee shot. Only the biggest hitters will be able to clear the water with their second shots. Do you have what it takes?
Hole 16 at University Park Golf Club

4. 623 Yards - Hole 16

University Park Golf Club

University Park, Illinois
Course length: 6,750 yards
From the back tees on hole 16 at University Park, you need to drive it 265 yards to reach the fairway. Said fairway is about 25 yards wide, but there’s no bunkers to worry about unless you’re way offline. Unfortunately you do need to worry about the figure eight-shaped pond on the left side of the green.

Fun fact about this hole: it is not the #1 handicap hole. It’s #2. At this length, it’s obviously a challenging ordeal. So challenging, in fact, that both very good and just-average golfers are likely to struggle with the hole. And that’s a clue to how the golf hole handicapping system works. The handicap rank of each hole isn’t just based on difficulty; it’s based on the disparity in scores between very good players vs average players.
Hole 8 at Whisper Creek Golf Club

5. 616 Yards - Hole 8

Whisper Creek Golf Club

Huntley, Illinois
Course length: 7,103 yards
Number 8 at Whisper Creek gives you a lot to think about. First of all, can we talk about the tee box names? There’s five tees and they’re called Oak, Pine, Birch, Willow, and Maple. Somewhat pretentious and confusing? Yes. But more immediately, golfers face loads of problems on the mighty 8th hole. The South Branch Kishwaukee River runs directly through the heart of it. The S-shaped layout presents confusing angles off the tee box and second shots. The fairway narrows considerably for your opening tee shot. Robust fescue grasses, wetlands, and even homes line the hole on this prairie-links style track -- all obstacles that can ruin your front-9 score. Proceed with extreme caution and vigilance.
Hole 18 at Stonewall Orchard Golf Club

T6. 615 Yards - Hole 18

Stonewall Orchard Golf Club

Grayslake, Illinois
Course length: 7,124 yards
To be considered a great course, it really helps to have a great finishing hole. Hole 18 at Stonewall Orchard is exactly that. This beauty of a track way up in Grayslake is long, scenic, and a blast to play. Stonewall is the second most difficult course on this list (after Dubsdread) and it helps to think your way around the course, rather than just grip it and rip it. That holds true on this final hole too. The green is narrow and flanked by water. The fairway approaching the narrow green forks into two paths. The left path is more direct, but narrow and flirts with the water; the right is wider, but elevated and further away.

I find it somewhat surprising that of all the long holes in this list, Stonewall’s is the only finishing hole.
Hole 6 at Foxford Hills Golf Club

T6. 615 Yards - Hole 6

Foxford Hills Golf Club

Cary, Illinois
Course length: 7,047 yards
With a rating of 74.6 and slope of 142 from the back tees, Foxford Hills is the third most difficult course in this top 10. Golfers will notice the massive dogleg left immediately, along with the nice, wide fairway. It’s generous, however it’s littered with fairway bunkers. In fact, there’s four bunkers in the heart of the fairway itself, a particularly cruel feature for an extremely lengthy hole. Overall, 16 bunkers aim to thwart your progress.
Hole 9 at Cog Hill #4 (Dubsdread)

T8. 613 Yards - Hole 9

Cog Hill Course #4 - Dubsdread

Palos Park, Illinois
Course length: 7,554 yards
By far the most prestigious course on this list (not to mention the most expensive by a mile) is Cog Hill #4, Dubsdread. The site of PGA Tour events for decades, along with various USGA championships, it has hosted the world’s best numerous times. Tiger Woods holds the course record here with an incredible 62 at the BMW Championship in 2009. Here’s a video of him playing the 9th hole that year, making a wild birdie from humble beginnings.

Large, mature trees encroach the narrow fairway, compounding any small mistakes. And like many greens at Dubsdread, this one is elevated and protected like a fortress by large bunkers. Just a devilishly difficult way to finish the front 9.
Hole 11 at White Pines Golf Club

T8. 613 Yards - Hole 11

White Pines West Course

Bensenville, Illinois
Course length: 6,624 yards
The driving range at White Pines is only about 250 yards deep, so you’ll just have to mentally visualize the massive bomb you’ll hit on the 11th hole when practicing. The dogleg left is narrow with lots of tree coverage, so take dead aim. A creek runs perpendicular to the fairway about 40 yards short of the green. That green is small and narrow. Godspeed.
Hole 12 at Tamarach Golf Club

T8. 613 Yards - Hole 12

Tamarack Golf Club

Naperville, Illinois
Course length: 6,901 yards
The DuPage River flows about 1.5 miles east of Tamarack and supplies a tremendous amount of water on the course. Hole 12 is a major beneficiary, with a pond by the tee box, and a creek that cuts across the fairway and then alongside it. But pick your poison -- water on the left, or 11 giant fairway bunkers on the right.
Hole 9 at Big Run Golf Club

Bonus hole

11. 610 Yards - Hole 9

Big Run Golf Club

Lockport, Illinois
Course length: 7,050 yards
Big Run has fun elevation changes and can be a tough walk on a hot day. The long 9th hole has a valley of sorts in the middle, adding to the complexity of the sweeping dogleg right setup. The fairway is only about 20 yards wide. Large trees try to box you out as if they were grabbing rebounds on the court all day. This is an extremely challenging hole, yet Big Run sports another 600 yard affair -- hole #15.

View GolfScout's Golf Courses

Anetsberger Golf Course
Apple Orchard Golf Course
Arboretum Club
Arlington Lakes Golf Club
Arrowhead East Course
Arrowhead South Course
Arrowhead West Course
Bartlett Hills Golf Club
Belmont Golf Club
Big Run Golf Club
Billy Caldwell Golf Course
Bittersweet Golf Club
Blackberry Oaks Golf Course
Blackstone Golf Club
Bliss Creek Golf Course
Bloomingdale Golf Club
Bolingbrook Golf Club
Bonnie Brook Golf Course
Bonnie Dundee Golf Club
Boone Creek Golf Club - Creekside Course
Boone Creek Golf Club - Prairie Course
Boone Creek Golf Club - Valley Course
Boughton Ridge Golf Course
Bowes Creek Country Club
Brae Loch Golf Club
Bridges of Poplar Creek Country Club
Broken Arrow Golf Club - East Course
Broken Arrow Golf Club - North Course
Broken Arrow Golf Club - South Course
Buffalo Grove Golf Course
Burnham Woods Golf Course
Canal Shores Golf Course
Cantigny Hillside Course
Cantigny Lakeside Course
Cantigny Woodside Course
Carriage Greens Country Club
Cary Country Club
Centennial Park Golf Course
Chalet Hills Golf Club
Chapel Hill Country Club
Chevy Chase Country Club
Chicago Heights East Golf Course
Chicago Heights West Golf Course
Chick Evans Golf Course
Cog Hill Course #1
Cog Hill Course #2 - Ravines
Cog Hill Course #3
Cog Hill Course #4 - Dubsdread
Columbus Park Golf Course
Countryside Prairie Course
Countryside Traditional Course
Coyote Run Golf Course
Craig Woods Golf Club
Crane's Landing Golf Club
Crystal Woods Golf Club
Deer Creek Golf Club
Deerfield Golf Club & Learning Center
Deerpath Golf Course
Eaglewood Resort Golf Club
Edgebrook Golf Course
Flagg Creek Golf Course
Foss Park Golf Course
Fountain Hills Golf Club
Fox Bend Golf Course
Fox Lake Country Club
Fox Run Golf Links
Foxford Hills Golf Club
Fresh Meadow Golf Club
George W. Dunne National
Glencoe Golf Club
Glendale Lakes Golf Club
Glenview Park Golf Club
Glenview Prairie Club
Glenwoodie Golf Club
Golf Center Des Plaines
Golf Club of Illinois
Grayslake Golf Course
Green Meadows Golf Course
Greenshire Golf Course
Harborside International - Port Course
Harborside International - Starboard Course
HeatherRidge Golf Course
Heritage Oaks Golf Club - Classic 18
Hickory Hills Country Club
Hickory Knoll Golf Course
Highland Woods Golf Course
Highlands of Elgin Golf Course
Hilldale Golf Club
Hughes Creek Golf Club
Indian Boundary Golf Course
Inwood Golf Course
Jackson Park Golf Course
Joe Louis “The Champ” Golf Course
Klein Creek Golf Club
Lake Bluff Golf Club
Lake Park Golf Course
Lincoln Oaks Golf Course
Links at Carillon - Blue Course
Links at Carillon - Red Course
Links at Carillon - White Course
Lombard Golf Course
Lost Marsh Golf Course
Makray Memorial Golf Club
Maple Meadows Golf Course
Marengo Ridge Golf Club
Marquette Park Golf Course
Meadowlark Golf Course
Meadows Golf Club of Blue Island
Midlane Country Club
Mill Creek Golf Club
Mistwood Golf Club
Mt. Prospect Golf Club
Naperbrook Golf Course
Nickol Knoll Golf Club
Oak Brook Golf Club
Oak Hills Country Club
Odyssey Golf Foundation
Old Oak Country Club
Old Orchard Country Club
Old Top Farm Golf Course
Orchard Valley Golf Course
Palatine Hills Golf Course
Palos Country Club
Palos Hills Golf Club
Phillips Park Golf Course
Pine Meadow Golf Club
Pinecrest Golf Club
Pottawatomie Golf Course
Prairie Bluff Golf Club
Prairie Isle Golf Course
Prairie Landing Golf Club
Randall Oaks Golf Club
Ravisloe Country Club
RedTail Golf Club
Renwood Golf Course
River Bend Golf Club
River Oaks Golf Course
Rob Roy Golf Course
Robert A. Black Golf Course
Ruffled Feathers Golf Club
Salt Creek Golf Club
Sanctuary Golf Course
Schaumburg Golf Club - Baer Course
Schaumburg Golf Club - Players Course
Schaumburg Golf Club - Tournament Course
Settler's Hill Golf Course
Seven Bridges Golf Club
Shepherd's Crook Golf Course
Shiloh Park Golf Course
Silver Lake North Course
Silver Lake Rolling Hills Course
Silver Lake South Course
South Shore Golf Course
Springbrook Golf Course
Square Links Golf Course
St. Andrews - Joe Jemsek Course
St. Andrews - St. Andrews Course
Steeple Chase Golf Club
Stonewall Orchard Golf Club
Stony Creek Golf Course
Streamwood Oaks Golf Club
Sugar Creek Golf Course
Sunset Valley Golf Club
Sydney R. Marovitz Golf Course
Tam O'Shanter Golf Course
Tamarack Golf Club
Tanna Farms Golf Club
The Glen Club
The Preserve at Oak Meadows
Thunderhawk Golf Club
Twin Lakes Golf Club
Twin Lakes Golf Course
University Park Golf Club
Valley Ridge Golf Course
Vernon Hills Golf Course
Veterans Memorial Golf Course
Villa Olivia Golf Course
Village Green Golf Course
Village Greens of Woodridge
Village Links of Glen Ellyn - 18 Hole Course
Village Links of Glen Ellyn - 9 Hole Course
Water’s Edge Golf Club
Wedgewood Golf Course
Whisper Creek Golf Club
White Deer Run Golf Club
White Mountain Golf Park
White Pines East Course
White Pines West Course
Whitetail Ridge Golf Club
Willow Crest Golf Club
Willow Hill Golf Course
Wilmette Golf Club
Wing Park Golf Course
Winnetka Golf Club
Woodruff Golf Course
Zigfield Troy Golf