Tired of the usual stroke-play grind or the same old fourball match? The Chicago golf game is a fantastic alternative that levels the playing field for golfers of all abilities, making every hole an exciting battle for points. This guide will walk you through exactly how to set up, score, and strategize your way to victory in your next Chicago match.
At its heart, the Chicago golf game is a points-based competition managed by handicaps. Unlike traditional games where you compare your total score to others, in Chicago, each player competes against their own personal points target, or "quota." The goal is simply to accumulate as many points as posssible and beat your individual quota by the largest margin.
This structure is brilliant because it allows a 25-handicapper to have a fair and genuinely competitive match against a 5-handicapper. Success isn't about who shoots the lowest gross score, it's about who plays best relative to their own ability. It’s an ideal format for your regular weekend group of three or four, adding an extra layer of strategy and excitement to the round.
Getting a Chicago match started is straightforward, but it requires two key steps before you stick a peg in the ground. Getting this part right is essential for a fair game.
The "quota" is the target number of points each player needs to achieve. This is the handicap system for the game, and it’s what creates a level playing field. The standard formula to calculate a player's quota is:
39 minus the player's Course Handicap
It's important to use the Course Handicap, not a player's general Handicap Index. Your Course Handicap automatically adjusts for the difficulty of the specific course and tees you're playing that day. You can typically find this on the club's handicap computer, a mobile app, or by consulting the conversion chart in the pro shop.
Let's look at a few examples for a foursome:
As you can see, the higher the handicap, the fewer points a player needs to an "even" round. Their goal now is not to shoot par, but to score more points than their personal quota.
Once everyone knows their target, you have to decide what you're playing for. There are two primary ways to handle the betting in a Chicago match.
This is the easiest method to track. Every player puts an agreed-upon amount - say, $10 - into a central pot before the round. At the end of 18 holes, you calculate who exceeded their quota by the most points. That person wins the entire pot.
For example:
In this scenario, Player B is +3, which is the highest score relative to their quota. Player B wins the pot!
This is a more involved but often more exciting format where money changes hands based on every single point. Players decide on a value per point (e.g., $1). At the end of the round, you compare everyone's final score to their quota:
Using the same scores from above with a $1 point value:
The calculation is simple: Each payer gives their point difference to each winner.
Final tally:
This format keeps everyone engaged until the very last putt, as a single point on the 18th hole can swing the final results.
Scoring in Chicago is based on your gross score on each hole. Since the handicap has been factored into the quota at the start, you don't need to worry about net scores. This simplifies things greatly. While groups can tweak the values, here is the standard points system:
As you can see, the points jump significantly for better scores. This is where the strategy of the game really starts to take shape. You earn far more for a birdie than you lose for a bogey.
Let's track the first few holes for Player B from our example:
One person in the group should be designated as the scorekeeper to track the points for every player on every hole. It's much easier than trying to add it all up at the end.
Playing Chicago is different from normal stroke play. As a coach, I tell my students to shift their thinking from simply "avoiding mistakes" to "harvesting points." Here’s how you do it.
Look at the scoring table again. A single birdie (4 points) is worth the same as *four bogeys*. The path to beating your quota, especially for a lower handicapper, is through making birdies and eagles. It's a game of big payoffs.
Before your round, identify your best opportunities: the reachable par 5s, the short par 4s, the par 3s you feel confident on. On those holes, play with a more aggressive strategy. The risk is worth the reward. A failed birdie attempt that leads to a par is still 2 points. But converting just one or two of those aggressive plays into a 4-point birdie will completely change your score.
The worst thing you can do in Chicago is make a “0.” The difference between a bogey (1 point) and a double bogey (0 points) is colossal. One costs you nothing, the other gives you something valuable.
When you hit a bad drive and you’re deep in the trees, resist the urge to be a hero. Don't take on the 1-in-100 shot through a shoebox-sized gap in the branches. That’s how a bogey turns into a triple bogey. Instead, take your medicine. Punch out to the fairway, give yourself a wedge into the green, and try to make your putt for a 1-point bogey. Playing smart and avoiding the zeros is just as powerful as making birdies.
Don't fall into the trap of competing with the other players' scores hole by hole. Compete with your own target number. A high-handicapper with a quota of 17 doesn't need to make birdies to win. A round filled with bogeys (1 point) and five pars (2 points each) gets them to 18 points - and that might be enough to win the whole pot! Respect your own game. If your path to victory is grinding out pars and bogeys, embrace it.
The Chicago format makes golf a truly fair and strategic competition for any group. By establishing a unique point quota for each player, it challenges everyone to play their best relative to their abilities and rewards smart, aggressive play.
The key to winning at Chicago often comes down to course management - knowing when to attack for a 4-point birdie and when to play it safe to avoid that dreaded '0' on the scorecard. We built Caddie AI to give you that expert-level strategy on demand. When you’re faced with a tough decision, like how to play a tricky recovery shot, you can get immediate, simple guidance to help you choose the smartest play. It takes the guesswork out of those critical moments, helping you preserve those valuable points.
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