What is the fascination board gamers have with trains omggggggggggg
Chicago Express is kind of the anti-Ticket to Ride. There are no cards, no pre-determined track lines where your trains can go, and you don't even have your own set of trains. Instead, you buy stock in train companies and receive dividends at various points so you can turn around and buy more stock, or just sit on your cash like Scrooge McDuck. And the train companies pay for everything!
The way it works is thus: Each player can do one of three actions per turn. You can start an auction for one stock certificate of your choice, build up to three trains along the line of a company in which you own stock, or build a house in an area to increase the value of any train lines running through there. Running lines and building houses comes out of the money put into a company via stock purchases, so at the start you can only auction stock. This gives ownership stakes to players so they can use the other actions, and money to the companies so they can afford the other actions. However, only so many of each action can be used per turn (different number per action type), and they don't reset until two action types are maxed out.
Once those two action types are maxed, the round resets, and dividends are paid. Dividends are equal to the value of the company, and you receive a percentage of those dividends equal to the percentage of the purchased stock you have in that company. If you have the only stock that anyone's bought, you get it all; if you have one and another person has one, you get half; if you have two and another person has one, you get two-thirds. Early stock ends up being the most valuable, since it's purchased when players don't have much money, but gauging what something's going to be worth at that point is harder. In other words, you need to buy something early, but it's hard to know what to buy.
Chicago is, for the most part, the most valuable city on the map. (A couple others can become worth slightly more, but they require either time or spending on upgrades; see below.) Not only does it add a ton more value to your company than any random town, mountain, or forest, but when a company gets there, its shareholders get an extra dividend paid to them right away. Every train company wants to reach Chicago, but the game doesn't usually last long enough for that to happen. However, roaming a bit with your line to increase its value can be helpful, as long as you make it to Chicago eventually.
There are a few quirks thrown into the game. Detroit acts like a round counter; it slowly increases in value, and once it's worth eight money, the game is in its final round. It can be a good boost to swing one of the northern lines to Detroit before taking it to Chicago. Reaching that final round is unusual, however, and you have to get to Chicago before the game ends.
Pittsburgh and Wheeling can be repeatedly increased through building houses, unlike other areas. Pittsburgh is sometimes worth it; there are usually better options than pumping Wheeling up one dollar at a time, which largely plays to how West Virginia is treated in the real world. And, once a company reaches Chicago, the Wabash company opens up. It only has two shares, but it starts in Fort Wayne and can reach Chicago pretty quickly.
The quirks don't overtake the main concept, though: everything is balanced around how well you judge the value of a company's stock, and how well you improve that value once you have a stake in it. Wabash is special because it comes into the game late and has a short path to Chicago, but that doesn't make it more valuable than the other companies; bidding wars can easily happen because there are only two shares, and that's often a mistake. Getting half of fourteen is not as good as getting one-quarter of thirty-six. (The answers are seven and nine.) It's a nice change from the automatic, whatever opens up last is best idea that games tend to have. And it's not really a secret from new players; the logic may not be immediately obvious, but if you're cognizant of how value works and can see what's possible or probable before the game ending conditions are met, you can take advantage.
I'm not a huge fan of this game because I'm bad at it. If it turns out you're not bad at it, you'll probably have a swell time.
Score: Six broken-down mining towns out of seven.