Ever heard a playing partner suggest a game of Chicago on the first tee and you just nodded along, completely unsure of the rules? You’re not alone. While not as common as a Scramble or Best Ball, the Chicago format is one of the most exciting and fair betting games you can play, perfectly designed to make a round with your buddies competitive, no matter their skill level. This guide breaks down everything you need to know about the format, from its unique scoring system to the on-course strategy that will help you take home the cash.
At its heart, the Chicago format is a points-based game where individuals compete against a "quota" or target score determined by their handicap. Instead of counting your total strokes, you earn points for your performance on each hole: eagles, birdies, pars, and even bogeys have a point value. The goal isn't to shoot the lowest score, but to accumulate the most points over 18 holes and finish with the highest positive score relative to your personal quota.
The beauty of Chicago is that it levels the playing field. A golfer who shoots 100 has a legitimate chance to beat a player who shoots 75 because their point targets are adjusted accordingly. It also changes your mindset. A blow-up hole that would kill your score in stroke play simply results in zero points in Chicago, allowing you to shake it off and focus on scoring points on the very next hole. It's a game that promotes recovery, aggression, and most of all, fun.
The system might sound a little complex at first, but once you play a hole or two, it becomes second nature. It's essentially a two-part process: first, you figure out every player's point target for the round, and second, you start awarding points hole-by-hole. Let’s walk through it.
This is the element that makes Chicago so balanced. Before the round begins, every player calculates their individual point target, or "quota." The most common formula used to determine this number is 39 minus the player's course handicap.
A "course handicap" is simply your handicap index adiusted for the difficulty of the specific course and tees you are playing from. If you're not an official handicap holder, you can use an honest estimate of your average score (e.g., if you usually shoot around 90, your handicap is roughly 18). Let's look at a few examples of how to calculate the quota:
As you can see, a player with a higher handicap has a much lower point target to meet, which is what allows them to compete directly against much better players.
Once the quotas are set, play begins. The scoring is simple and is based on your gross score - your actual strokes - on each hole. The standard point breakdown is as follows:
Note: Sometimes groups will add more excitement with extra points for big scores (an Eagle might be 8 points and an Albatross 16 points), or even introduce negative points for bad holes (-1 for a double bogey). For your first time, however, sticking to the standard points above is the easiest way to go.
This is where it all comes together. Simply tally up the total points you earned throughout the 18 holes. Then, you subtract your starting quota from your point total. The result is your final Chicago score. The player with the highest final score wins the game (or the money).
Let's play out a hypothetical scenario with two friends, Frank and Susan.
After 18 holes, they add up their points:
Frank's Round: He had a solid day with 2 Birdies (8 pts), 8 Pars (16 pts), and 7 Bogeys (7 pts). His total points are 8 + 16 + 7 = 31 points.
Susan's Round: She struggled a bit but managed to avoid any major disasters. She made 4 Pars (8 pts), 9 Bogeys (9 pts), and five double bogeys (0 pts). Her total points are 8 + 9 = 17 points.
Now, let's calculate their final Chicago scores:
Although Susan shot a much higher stroke play score than Frank, the game was extremely close. Frank wins by a single point! If the bet was $1 a point, Susan would owe Frank $1. This is a perfect illustration of how the format creates a very competitive match between players of different abilities.
Beyond being a fair betting game, Chicago offers some great benefits that can make any round more enjoyable, especially for casual golfers.
As we've seen, this is the format's greatest strength. The quota system acts as a built-in equalizer. It stops the low handicapper from running away with the game and prevents the high handicapper from feeling like they have no chance. If you have a regular group with a wide range of skill levels, Chicago is one of the best formats to ensure everyone stays engaged for all 18 holes.
This is a an excellent benefit. In stroke play, one triple or quadruple bogey can wreck your score and your mood. Pockets are full, heads are down. In Chicago, disaster is limited to zero points. Once you’ve made a double bogey on a hole, you're at 0 and can’t do any more damage. This encourages players to simply pick up their ball and move to the next hole, which is fantastic for pace of play. No more watching your buddy grind over a putt for an 8 when it doesn't matter!
The "pick up" rule also keeps morale high. Instead of dwelling on a tough hole, you can immediately refocus on the next one as a fresh opportunity to score points. A birdie is worth four times as much as a bogey, so making just one great hole can completely offset a few poor ones. This positive scoring system encourages a more resilient and attacking mindset, which is always more fun.
Chicago isn't just about luck, playing with the right strategy can significantly increase your chances of winning. Here are a few tips from a coaching perspective.
For mid-to-high handicap players, the game-winning strategy isn't chasing birdies - it's eliminating zeroes. Earning at least 1 point for a bogey on every single hole gives you a baseline of 18 points. For a 21-handicapper with a quota of 18 (39-21), a round of all bogeys would mean you finish at 0, a very respectable score. See every hole as a mission to secure at least one point. Avoiding the blow-up is more valuable than making a single birdie.
If you're a low-handicap player with a high quota, playing for bogeys won't be enough. You need to hunt for pars and birdies. Since the penalty for a mistake is capped at losing a few potential points (not strokes), Chicago rewards calculated aggression. If you have a chance to go for a par-5 in two or attack a "sucker" pin, it might be worth the risk. A birdie nets you 4 points, a significant boost that can make up for a zero an another hole.
Smart Chicago players have a great sense of self-awareness. If you hit your drive into the woods, take a drop, and then duff your third shot, the hole is likely gone. You’re lying 4 and still not on the green. Instead of trying for a heroic shot to save a bogey (1 point), recognize that the risk of making things worse is high. The smart play is to just get the ball back in play, accept you're probably getting a 0 on this hole, and reset for the next tee. Don’t let one bad decision bleed into two or three.
Chicago is a fantastic golf format that brings a fresh, strategic element to your regular games. By using a handicap-based quota and a forgiving points system, it makes every round competitive and fast-paced, highlighting good shots while minimizing the pain of the inevitable bad holes.
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